diff --git a/src/interface/web/app/chat/page.tsx b/src/interface/web/app/chat/page.tsx
index c3d5ff37..966cdd17 100644
--- a/src/interface/web/app/chat/page.tsx
+++ b/src/interface/web/app/chat/page.tsx
@@ -8,7 +8,7 @@ import ChatHistory from "../components/chatHistory/chatHistory";
 import { useSearchParams } from "next/navigation";
 import Loading from "../components/loading/loading";
 
-import { processMessageChunk } from "../common/chatFunctions";
+import { generateNewTitle, processMessageChunk } from "../common/chatFunctions";
 
 import "katex/dist/katex.min.css";
 
@@ -19,7 +19,11 @@ import {
     StreamMessage,
 } from "../components/chatMessage/chatMessage";
 import { useIPLocationData, useIsMobileWidth, welcomeConsole } from "../common/utils";
-import { ChatInputArea, ChatOptions } from "../components/chatInputArea/chatInputArea";
+import {
+    AttachedFileText,
+    ChatInputArea,
+    ChatOptions,
+} from "../components/chatInputArea/chatInputArea";
 import { useAuthenticatedData } from "../common/auth";
 import { AgentData } from "../agents/page";
 
@@ -30,7 +34,7 @@ interface ChatBodyDataProps {
     setQueryToProcess: (query: string) => void;
     streamedMessages: StreamMessage[];
     setStreamedMessages: (messages: StreamMessage[]) => void;
-    setUploadedFiles: (files: string[]) => void;
+    setUploadedFiles: (files: AttachedFileText[] | undefined) => void;
     isMobileWidth?: boolean;
     isLoggedIn: boolean;
     setImages: (images: string[]) => void;
@@ -77,7 +81,24 @@ function ChatBodyData(props: ChatBodyDataProps) {
                 setIsInResearchMode(true);
             }
         }
-    }, [setQueryToProcess, props.setImages]);
+
+        const storedUploadedFiles = localStorage.getItem("uploadedFiles");
+
+        if (storedUploadedFiles) {
+            const parsedFiles = storedUploadedFiles ? JSON.parse(storedUploadedFiles) : [];
+            const uploadedFiles: AttachedFileText[] = [];
+            for (const file of parsedFiles) {
+                uploadedFiles.push({
+                    name: file.name,
+                    file_type: file.file_type,
+                    content: file.content,
+                    size: file.size,
+                });
+            }
+            localStorage.removeItem("uploadedFiles");
+            props.setUploadedFiles(uploadedFiles);
+        }
+    }, [setQueryToProcess, props.setImages, conversationId]);
 
     useEffect(() => {
         if (message) {
@@ -100,6 +121,7 @@ function ChatBodyData(props: ChatBodyDataProps) {
         ) {
             setProcessingMessage(false);
             setImages([]); // Reset images after processing
+            props.setUploadedFiles(undefined); // Reset uploaded files after processing
         } else {
             setMessage("");
         }
@@ -153,7 +175,7 @@ export default function Chat() {
     const [messages, setMessages] = useState<StreamMessage[]>([]);
     const [queryToProcess, setQueryToProcess] = useState<string>("");
     const [processQuerySignal, setProcessQuerySignal] = useState(false);
-    const [uploadedFiles, setUploadedFiles] = useState<string[]>([]);
+    const [uploadedFiles, setUploadedFiles] = useState<AttachedFileText[] | undefined>(undefined);
     const [images, setImages] = useState<string[]>([]);
 
     const locationData = useIPLocationData() || {
@@ -192,6 +214,7 @@ export default function Chat() {
                 timestamp: new Date().toISOString(),
                 rawQuery: queryToProcess || "",
                 images: images,
+                queryFiles: uploadedFiles,
             };
             setMessages((prevMessages) => [...prevMessages, newStreamMessage]);
             setProcessQuerySignal(true);
@@ -224,6 +247,9 @@ export default function Chat() {
                 setQueryToProcess("");
                 setProcessQuerySignal(false);
                 setImages([]);
+
+                if (conversationId) generateNewTitle(conversationId, setTitle);
+
                 break;
             }
 
@@ -273,6 +299,7 @@ export default function Chat() {
                 timezone: locationData.timezone,
             }),
             ...(images.length > 0 && { images: images }),
+            ...(uploadedFiles && { files: uploadedFiles }),
         };
 
         const response = await fetch(chatAPI, {
@@ -325,7 +352,7 @@ export default function Chat() {
             <div>
                 <SidePanel
                     conversationId={conversationId}
-                    uploadedFiles={uploadedFiles}
+                    uploadedFiles={[]}
                     isMobileWidth={isMobileWidth}
                 />
             </div>
diff --git a/src/interface/web/app/common/chatFunctions.ts b/src/interface/web/app/common/chatFunctions.ts
index a42dde40..b4777ba8 100644
--- a/src/interface/web/app/common/chatFunctions.ts
+++ b/src/interface/web/app/common/chatFunctions.ts
@@ -267,6 +267,78 @@ export async function createNewConversation(slug: string) {
     }
 }
 
+export async function packageFilesForUpload(files: FileList): Promise<FormData> {
+    const formData = new FormData();
+
+    const fileReadPromises = Array.from(files).map((file) => {
+        return new Promise<void>((resolve, reject) => {
+            let reader = new FileReader();
+            reader.onload = function (event) {
+                if (event.target === null) {
+                    reject();
+                    return;
+                }
+
+                let fileContents = event.target.result;
+                let fileType = file.type;
+                let fileName = file.name;
+                if (fileType === "") {
+                    let fileExtension = fileName.split(".").pop();
+                    if (fileExtension === "org") {
+                        fileType = "text/org";
+                    } else if (fileExtension === "md") {
+                        fileType = "text/markdown";
+                    } else if (fileExtension === "txt") {
+                        fileType = "text/plain";
+                    } else if (fileExtension === "html") {
+                        fileType = "text/html";
+                    } else if (fileExtension === "pdf") {
+                        fileType = "application/pdf";
+                    } else if (fileExtension === "docx") {
+                        fileType =
+                            "application/vnd.openxmlformats-officedocument.wordprocessingml.document";
+                    } else {
+                        // Skip this file if its type is not supported
+                        resolve();
+                        return;
+                    }
+                }
+
+                if (fileContents === null) {
+                    reject();
+                    return;
+                }
+
+                let fileObj = new Blob([fileContents], { type: fileType });
+                formData.append("files", fileObj, file.name);
+                resolve();
+            };
+            reader.onerror = reject;
+            reader.readAsArrayBuffer(file);
+        });
+    });
+
+    await Promise.all(fileReadPromises);
+    return formData;
+}
+
+export function generateNewTitle(conversationId: string, setTitle: (title: string) => void) {
+    fetch(`/api/chat/title?conversation_id=${conversationId}`, {
+        method: "POST",
+    })
+        .then((res) => {
+            if (!res.ok) throw new Error(`Failed to call API with error ${res.statusText}`);
+            return res.json();
+        })
+        .then((data) => {
+            setTitle(data.title);
+        })
+        .catch((err) => {
+            console.error(err);
+            return;
+        });
+}
+
 export function uploadDataForIndexing(
     files: FileList,
     setWarning: (warning: string) => void,
diff --git a/src/interface/web/app/common/iconUtils.tsx b/src/interface/web/app/common/iconUtils.tsx
index b6391d1b..f266cac5 100644
--- a/src/interface/web/app/common/iconUtils.tsx
+++ b/src/interface/web/app/common/iconUtils.tsx
@@ -49,8 +49,11 @@ import {
     Gavel,
     Broadcast,
     KeyReturn,
+    FilePdf,
+    FileMd,
+    MicrosoftWordLogo,
 } from "@phosphor-icons/react";
-import { Markdown, OrgMode, Pdf, Word } from "@/app/components/logo/fileLogo";
+import { OrgMode } from "@/app/components/logo/fileLogo";
 
 interface IconMap {
     [key: string]: (color: string, width: string, height: string) => JSX.Element | null;
@@ -238,11 +241,12 @@ function getIconFromFilename(
             return <OrgMode className={className} />;
         case "markdown":
         case "md":
-            return <Markdown className={className} />;
+            return <FileMd className={className} />;
         case "pdf":
-            return <Pdf className={className} />;
+            return <FilePdf className={className} />;
         case "doc":
-            return <Word className={className} />;
+        case "docx":
+            return <MicrosoftWordLogo className={className} />;
         case "jpg":
         case "jpeg":
         case "png":
diff --git a/src/interface/web/app/common/utils.ts b/src/interface/web/app/common/utils.ts
index 6c10ba8a..efa2c1d3 100644
--- a/src/interface/web/app/common/utils.ts
+++ b/src/interface/web/app/common/utils.ts
@@ -71,6 +71,16 @@ export function useIsMobileWidth() {
     return isMobileWidth;
 }
 
+export const convertBytesToText = (fileSize: number) => {
+    if (fileSize < 1024) {
+        return `${fileSize} B`;
+    } else if (fileSize < 1024 * 1024) {
+        return `${(fileSize / 1024).toFixed(2)} KB`;
+    } else {
+        return `${(fileSize / (1024 * 1024)).toFixed(2)} MB`;
+    }
+};
+
 export function useDebounce<T>(value: T, delay: number): T {
     const [debouncedValue, setDebouncedValue] = useState<T>(value);
 
diff --git a/src/interface/web/app/components/chatHistory/chatHistory.tsx b/src/interface/web/app/components/chatHistory/chatHistory.tsx
index 772f1d35..ea566df4 100644
--- a/src/interface/web/app/components/chatHistory/chatHistory.tsx
+++ b/src/interface/web/app/components/chatHistory/chatHistory.tsx
@@ -373,6 +373,7 @@ export default function ChatHistory(props: ChatHistoryProps) {
                                             images: message.images,
                                             conversationId: props.conversationId,
                                             turnId: messageTurnId,
+                                            queryFiles: message.queryFiles,
                                         }}
                                         customClassName="fullHistory"
                                         borderLeftColor={`${data?.agent?.color}-500`}
diff --git a/src/interface/web/app/components/chatInputArea/chatInputArea.tsx b/src/interface/web/app/components/chatInputArea/chatInputArea.tsx
index a036ccb3..88a4fcae 100644
--- a/src/interface/web/app/components/chatInputArea/chatInputArea.tsx
+++ b/src/interface/web/app/components/chatInputArea/chatInputArea.tsx
@@ -40,19 +40,36 @@ import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from "@/comp
 import { convertColorToTextClass, convertToBGClass } from "@/app/common/colorUtils";
 
 import LoginPrompt from "../loginPrompt/loginPrompt";
-import { uploadDataForIndexing } from "../../common/chatFunctions";
 import { InlineLoading } from "../loading/loading";
-import { getIconForSlashCommand } from "@/app/common/iconUtils";
+import { getIconForSlashCommand, getIconFromFilename } from "@/app/common/iconUtils";
+import { packageFilesForUpload } from "@/app/common/chatFunctions";
+import { convertBytesToText } from "@/app/common/utils";
+import {
+    Dialog,
+    DialogContent,
+    DialogDescription,
+    DialogHeader,
+    DialogTitle,
+    DialogTrigger,
+} from "@/components/ui/dialog";
+import { ScrollArea } from "@/components/ui/scroll-area";
 
 export interface ChatOptions {
     [key: string]: string;
 }
 
+export interface AttachedFileText {
+    name: string;
+    content: string;
+    file_type: string;
+    size: number;
+}
+
 interface ChatInputProps {
     sendMessage: (message: string) => void;
     sendImage: (image: string) => void;
     sendDisabled: boolean;
-    setUploadedFiles?: (files: string[]) => void;
+    setUploadedFiles: (files: AttachedFileText[]) => void;
     conversationId?: string | null;
     chatOptionsData?: ChatOptions | null;
     isMobileWidth?: boolean;
@@ -75,6 +92,9 @@ export const ChatInputArea = forwardRef<HTMLTextAreaElement, ChatInputProps>((pr
     const [imagePaths, setImagePaths] = useState<string[]>([]);
     const [imageData, setImageData] = useState<string[]>([]);
 
+    const [attachedFiles, setAttachedFiles] = useState<FileList | null>(null);
+    const [convertedAttachedFiles, setConvertedAttachedFiles] = useState<AttachedFileText[]>([]);
+
     const [recording, setRecording] = useState(false);
     const [mediaRecorder, setMediaRecorder] = useState<MediaRecorder | null>(null);
 
@@ -154,6 +174,8 @@ export const ChatInputArea = forwardRef<HTMLTextAreaElement, ChatInputProps>((pr
         }
 
         props.sendMessage(messageToSend);
+        setAttachedFiles(null);
+        setConvertedAttachedFiles([]);
         setMessage("");
     }
 
@@ -203,22 +225,69 @@ export const ChatInputArea = forwardRef<HTMLTextAreaElement, ChatInputProps>((pr
             setImagePaths((prevPaths) => [...prevPaths, ...newImagePaths]);
             // Set focus to the input for user message after uploading files
             chatInputRef?.current?.focus();
-            return;
         }
 
-        uploadDataForIndexing(
-            files,
-            setWarning,
-            setUploading,
-            setError,
-            props.setUploadedFiles,
-            props.conversationId,
+        // Process all non-image files
+        const nonImageFiles = Array.from(files).filter(
+            (file) => !image_endings.includes(file.name.split(".").pop() || ""),
         );
 
+        // Concatenate attachedFiles and files
+        const newFiles = nonImageFiles
+            ? Array.from(nonImageFiles).concat(Array.from(attachedFiles || []))
+            : Array.from(attachedFiles || []);
+
+        // Ensure files are below size limit (10 MB)
+        for (let i = 0; i < newFiles.length; i++) {
+            if (newFiles[i].size > 10 * 1024 * 1024) {
+                setWarning(
+                    `File ${newFiles[i].name} is too large. Please upload files smaller than 10 MB.`,
+                );
+                return;
+            }
+        }
+
+        const dataTransfer = new DataTransfer();
+        newFiles.forEach((file) => dataTransfer.items.add(file));
+        setAttachedFiles(dataTransfer.files);
+
+        // Extract text from files
+        extractTextFromFiles(dataTransfer.files).then((data) => {
+            props.setUploadedFiles(data);
+            setConvertedAttachedFiles(data);
+        });
+
         // Set focus to the input for user message after uploading files
         chatInputRef?.current?.focus();
     }
 
+    async function extractTextFromFiles(files: FileList): Promise<AttachedFileText[]> {
+        const formData = await packageFilesForUpload(files);
+        setUploading(true);
+
+        try {
+            const response = await fetch("/api/content/convert", {
+                method: "POST",
+                body: formData,
+            });
+            setUploading(false);
+
+            if (!response.ok) {
+                throw new Error(`HTTP error! status: ${response.status}`);
+            }
+
+            return await response.json();
+        } catch (error) {
+            setError(
+                "Error converting files. " +
+                    error +
+                    ". Please try again, or contact team@khoj.dev if the issue persists.",
+            );
+            console.error("Error converting files:", error);
+            return [];
+        }
+    }
+
     // Assuming this function is added within the same context as the provided excerpt
     async function startRecordingAndTranscribe() {
         try {
@@ -445,6 +514,93 @@ export const ChatInputArea = forwardRef<HTMLTextAreaElement, ChatInputProps>((pr
                 </div>
             )}
             <div>
+                <div className="flex items-center gap-2 overflow-x-auto">
+                    {imageUploaded &&
+                        imagePaths.map((path, index) => (
+                            <div key={index} className="relative flex-shrink-0 pb-3 pt-2 group">
+                                <img
+                                    src={path}
+                                    alt={`img-${index}`}
+                                    className="w-auto h-16 object-cover rounded-xl"
+                                />
+                                <Button
+                                    variant="ghost"
+                                    size="icon"
+                                    className="absolute -top-0 -right-2 h-5 w-5 rounded-full bg-neutral-200 dark:bg-neutral-600 hover:bg-neutral-300 dark:hover:bg-neutral-500 opacity-0 group-hover:opacity-100 transition-opacity"
+                                    onClick={() => removeImageUpload(index)}
+                                >
+                                    <X className="h-3 w-3" />
+                                </Button>
+                            </div>
+                        ))}
+                    {convertedAttachedFiles &&
+                        Array.from(convertedAttachedFiles).map((file, index) => (
+                            <Dialog key={index}>
+                                <DialogTrigger asChild>
+                                    <div key={index} className="relative flex-shrink-0 p-2 group">
+                                        <div
+                                            className={`w-auto h-16 object-cover rounded-xl ${props.agentColor ? convertToBGClass(props.agentColor) : "bg-orange-300 hover:bg-orange-500"} bg-opacity-15`}
+                                        >
+                                            <div className="flex p-2 flex-col justify-start items-start h-full">
+                                                <span className="text-sm font-bold text-neutral-500 dark:text-neutral-400 text-ellipsis truncate max-w-[200px] break-words">
+                                                    {file.name}
+                                                </span>
+                                                <span className="flex items-center gap-1">
+                                                    {getIconFromFilename(file.file_type)}
+                                                    <span className="text-xs text-neutral-500 dark:text-neutral-400">
+                                                        {convertBytesToText(file.size)}
+                                                    </span>
+                                                </span>
+                                            </div>
+                                        </div>
+                                        <Button
+                                            variant="ghost"
+                                            size="icon"
+                                            className="absolute -top-0 -right-2 h-5 w-5 rounded-full bg-neutral-200 dark:bg-neutral-600 hover:bg-neutral-300 dark:hover:bg-neutral-500 opacity-0 group-hover:opacity-100 transition-opacity"
+                                            onClick={() => {
+                                                setAttachedFiles((prevFiles) => {
+                                                    const removeFile = file.name;
+                                                    if (!prevFiles) return null;
+                                                    const updatedFiles = Array.from(
+                                                        prevFiles,
+                                                    ).filter((file) => file.name !== removeFile);
+                                                    const dataTransfer = new DataTransfer();
+                                                    updatedFiles.forEach((file) =>
+                                                        dataTransfer.items.add(file),
+                                                    );
+
+                                                    const filteredConvertedAttachedFiles =
+                                                        convertedAttachedFiles.filter(
+                                                            (file) => file.name !== removeFile,
+                                                        );
+
+                                                    props.setUploadedFiles(
+                                                        filteredConvertedAttachedFiles,
+                                                    );
+                                                    setConvertedAttachedFiles(
+                                                        filteredConvertedAttachedFiles,
+                                                    );
+                                                    return dataTransfer.files;
+                                                });
+                                            }}
+                                        >
+                                            <X className="h-3 w-3" />
+                                        </Button>
+                                    </div>
+                                </DialogTrigger>
+                                <DialogContent>
+                                    <DialogHeader>
+                                        <DialogTitle>{file.name}</DialogTitle>
+                                    </DialogHeader>
+                                    <DialogDescription>
+                                        <ScrollArea className="h-72 w-full rounded-md">
+                                            {file.content}
+                                        </ScrollArea>
+                                    </DialogDescription>
+                                </DialogContent>
+                            </Dialog>
+                        ))}
+                </div>
                 <div
                     className={`${styles.actualInputArea} justify-between dark:bg-neutral-700 relative ${isDragAndDropping && "animate-pulse"}`}
                     onDragOver={handleDragOver}
@@ -453,12 +609,14 @@ export const ChatInputArea = forwardRef<HTMLTextAreaElement, ChatInputProps>((pr
                 >
                     <input
                         type="file"
+                        accept=".pdf,.doc,.docx,.txt,.md,.org,.jpg,.jpeg,.png,.webp"
                         multiple={true}
                         ref={fileInputRef}
                         onChange={handleFileChange}
                         style={{ display: "none" }}
                     />
-                    <div className="flex items-end pb-2">
+
+                    <div className="flex items-center">
                         <Button
                             variant={"ghost"}
                             className="!bg-none p-0 m-2 h-auto text-3xl rounded-full text-gray-300 hover:text-gray-500"
@@ -469,29 +627,6 @@ export const ChatInputArea = forwardRef<HTMLTextAreaElement, ChatInputProps>((pr
                         </Button>
                     </div>
                     <div className="flex-grow flex flex-col w-full gap-1.5 relative">
-                        <div className="flex items-center gap-2 overflow-x-auto">
-                            {imageUploaded &&
-                                imagePaths.map((path, index) => (
-                                    <div
-                                        key={index}
-                                        className="relative flex-shrink-0 pb-3 pt-2 group"
-                                    >
-                                        <img
-                                            src={path}
-                                            alt={`img-${index}`}
-                                            className="w-auto h-16 object-cover rounded-xl"
-                                        />
-                                        <Button
-                                            variant="ghost"
-                                            size="icon"
-                                            className="absolute -top-0 -right-2 h-5 w-5 rounded-full bg-neutral-200 dark:bg-neutral-600 hover:bg-neutral-300 dark:hover:bg-neutral-500 opacity-0 group-hover:opacity-100 transition-opacity"
-                                            onClick={() => removeImageUpload(index)}
-                                        >
-                                            <X className="h-3 w-3" />
-                                        </Button>
-                                    </div>
-                                ))}
-                        </div>
                         <Textarea
                             ref={chatInputRef}
                             className={`border-none focus:border-none
@@ -582,10 +717,14 @@ export const ChatInputArea = forwardRef<HTMLTextAreaElement, ChatInputProps>((pr
                                 <span className="text-muted-foreground text-sm">Research Mode</span>
                                 {useResearchMode ? (
                                     <ToggleRight
+                                        weight="fill"
                                         className={`w-6 h-6 inline-block ${props.agentColor ? convertColorToTextClass(props.agentColor) : convertColorToTextClass("orange")} rounded-full`}
                                     />
                                 ) : (
-                                    <ToggleLeft className={`w-6 h-6 inline-block rounded-full`} />
+                                    <ToggleLeft
+                                        weight="fill"
+                                        className={`w-6 h-6 inline-block ${props.agentColor ? convertColorToTextClass(props.agentColor) : convertColorToTextClass("orange")} rounded-full`}
+                                    />
                                 )}
                             </Button>
                         </TooltipTrigger>
diff --git a/src/interface/web/app/components/chatMessage/chatMessage.tsx b/src/interface/web/app/components/chatMessage/chatMessage.tsx
index d05d9829..aae271b1 100644
--- a/src/interface/web/app/components/chatMessage/chatMessage.tsx
+++ b/src/interface/web/app/components/chatMessage/chatMessage.tsx
@@ -40,6 +40,18 @@ import { AgentData } from "@/app/agents/page";
 import renderMathInElement from "katex/contrib/auto-render";
 import "katex/dist/katex.min.css";
 import ExcalidrawComponent from "../excalidraw/excalidraw";
+import { AttachedFileText } from "../chatInputArea/chatInputArea";
+import {
+    Dialog,
+    DialogContent,
+    DialogDescription,
+    DialogHeader,
+    DialogTrigger,
+} from "@/components/ui/dialog";
+import { DialogTitle } from "@radix-ui/react-dialog";
+import { convertBytesToText } from "@/app/common/utils";
+import { ScrollArea } from "@/components/ui/scroll-area";
+import { getIconFromFilename } from "@/app/common/iconUtils";
 
 const md = new markdownIt({
     html: true,
@@ -149,6 +161,7 @@ export interface SingleChatMessage {
     images?: string[];
     conversationId: string;
     turnId?: string;
+    queryFiles?: AttachedFileText[];
 }
 
 export interface StreamMessage {
@@ -165,6 +178,7 @@ export interface StreamMessage {
     intentType?: string;
     inferredQueries?: string[];
     turnId?: string;
+    queryFiles?: AttachedFileText[];
 }
 
 export interface ChatHistoryData {
@@ -398,7 +412,6 @@ const ChatMessage = forwardRef<HTMLDivElement, ChatMessageProps>((props, ref) =>
         if (props.chatMessage.intent) {
             const { type, "inferred-queries": inferredQueries } = props.chatMessage.intent;
 
-            console.log("intent type", type);
             if (type in intentTypeHandlers) {
                 message = intentTypeHandlers[type as keyof typeof intentTypeHandlers](message);
             }
@@ -695,6 +708,40 @@ const ChatMessage = forwardRef<HTMLDivElement, ChatMessageProps>((props, ref) =>
             onMouseLeave={(event) => setIsHovering(false)}
             onMouseEnter={(event) => setIsHovering(true)}
         >
+            {props.chatMessage.queryFiles && props.chatMessage.queryFiles.length > 0 && (
+                <div className="flex flex-wrap flex-col m-2 max-w-full">
+                    {props.chatMessage.queryFiles.map((file, index) => (
+                        <Dialog key={index}>
+                            <DialogTrigger asChild>
+                                <div
+                                    className="flex items-center space-x-2 cursor-pointer bg-gray-500 bg-opacity-25 rounded-lg m-1 p-2 w-full
+                                "
+                                >
+                                    <div className="flex-shrink-0">
+                                        {getIconFromFilename(file.file_type)}
+                                    </div>
+                                    <span className="truncate flex-1 min-w-0">{file.name}</span>
+                                    {file.size && (
+                                        <span className="text-gray-400 flex-shrink-0">
+                                            ({convertBytesToText(file.size)})
+                                        </span>
+                                    )}
+                                </div>
+                            </DialogTrigger>
+                            <DialogContent>
+                                <DialogHeader>
+                                    <DialogTitle>{file.name}</DialogTitle>
+                                </DialogHeader>
+                                <DialogDescription>
+                                    <ScrollArea className="h-72 w-full rounded-md">
+                                        {file.content}
+                                    </ScrollArea>
+                                </DialogDescription>
+                            </DialogContent>
+                        </Dialog>
+                    ))}
+                </div>
+            )}
             <div className={chatMessageWrapperClasses(props.chatMessage)}>
                 <div
                     ref={messageRef}
diff --git a/src/interface/web/app/components/logo/fileLogo.tsx b/src/interface/web/app/components/logo/fileLogo.tsx
index 56bef3f7..e6e8217f 100644
--- a/src/interface/web/app/components/logo/fileLogo.tsx
+++ b/src/interface/web/app/components/logo/fileLogo.tsx
@@ -81,111 +81,3 @@ export function OrgMode({ className }: { className?: string }) {
         </svg>
     );
 }
-
-export function Markdown({ className }: { className?: string }) {
-    const classes = className ?? "w-6 h-6 text-muted-foreground inline-flex mr-1";
-    return (
-        <svg
-            className={`${classes}`}
-            xmlns="http://www.w3.org/2000/svg"
-            width="208"
-            height="128"
-            viewBox="0 0 208 128"
-        >
-            <rect
-                width="198"
-                height="118"
-                x="5"
-                y="5"
-                ry="10"
-                stroke="#000"
-                strokeWidth="10"
-                fill="none"
-            />
-            <path d="M30 98V30h20l20 25 20-25h20v68H90V59L70 84 50 59v39zm125 0l-30-33h20V30h20v35h20z" />
-        </svg>
-    );
-}
-
-export function Pdf({ className }: { className?: string }) {
-    const classes = className ?? "w-6 h-6 text-muted-foreground inline-flex mr-1";
-    return (
-        <svg
-            className={`${classes}`}
-            xmlns="http://www.w3.org/2000/svg"
-            enableBackground="new 0 0 334.371 380.563"
-            version="1.1"
-            viewBox="0 0 14 16"
-        >
-            <g transform="matrix(.04589 0 0 .04589 -.66877 -.73379)">
-                <polygon
-                    points="51.791 356.65 51.791 23.99 204.5 23.99 282.65 102.07 282.65 356.65"
-                    fill="#fff"
-                    strokeWidth="212.65"
-                />
-                <path
-                    d="m201.19 31.99 73.46 73.393v243.26h-214.86v-316.66h141.4m6.623-16h-164.02v348.66h246.85v-265.9z"
-                    strokeWidth="21.791"
-                />
-            </g>
-            <g transform="matrix(.04589 0 0 .04589 -.66877 -.73379)">
-                <polygon
-                    points="282.65 356.65 51.791 356.65 51.791 23.99 204.5 23.99 206.31 25.8 206.31 100.33 280.9 100.33 282.65 102.07"
-                    fill="#fff"
-                    strokeWidth="212.65"
-                />
-                <path
-                    d="m198.31 31.99v76.337h76.337v240.32h-214.86v-316.66h138.52m9.5-16h-164.02v348.66h246.85v-265.9l-6.43-6.424h-69.907v-69.842z"
-                    strokeWidth="21.791"
-                />
-            </g>
-            <g transform="matrix(.04589 0 0 .04589 -.66877 -.73379)" strokeWidth="21.791">
-                <polygon points="258.31 87.75 219.64 87.75 219.64 48.667 258.31 86.38" />
-                <path d="m227.64 67.646 12.41 12.104h-12.41v-12.104m-5.002-27.229h-10.998v55.333h54.666v-12.742z" />
-            </g>
-            <g
-                transform="matrix(.04589 0 0 .04589 -.66877 -.73379)"
-                fill="#ed1c24"
-                strokeWidth="212.65"
-            >
-                <polygon points="311.89 284.49 22.544 284.49 22.544 167.68 37.291 152.94 37.291 171.49 297.15 171.49 297.15 152.94 311.89 167.68" />
-                <path d="m303.65 168.63 1.747 1.747v107.62h-276.35v-107.62l1.747-1.747v9.362h272.85v-9.362m-12.999-31.385v27.747h-246.86v-27.747l-27.747 27.747v126h302.35v-126z" />
-            </g>
-            <rect x="1.7219" y="7.9544" width="10.684" height="4.0307" fill="none" />
-            <g transform="matrix(.04589 0 0 .04589 1.7219 11.733)" fill="#fff" strokeWidth="21.791">
-                <path d="m9.216 0v-83.2h30.464q6.784 0 12.928 1.408 6.144 1.28 10.752 4.608 4.608 3.2 7.296 8.576 2.816 5.248 2.816 13.056 0 7.68-2.816 13.184-2.688 5.504-7.296 9.088-4.608 3.456-10.624 5.248-6.016 1.664-12.544 1.664h-8.96v26.368zm22.016-43.776h7.936q6.528 0 9.6-3.072 3.2-3.072 3.2-8.704t-3.456-7.936-9.856-2.304h-7.424z" />
-                <path d="m87.04 0v-83.2h24.576q9.472 0 17.28 2.304 7.936 2.304 13.568 7.296t8.704 12.8q3.2 7.808 3.2 18.816t-3.072 18.944-8.704 13.056q-5.504 5.12-13.184 7.552-7.552 2.432-16.512 2.432zm22.016-17.664h1.28q4.48 0 8.448-1.024 3.968-1.152 6.784-3.84 2.944-2.688 4.608-7.424t1.664-12.032-1.664-11.904-4.608-7.168q-2.816-2.56-6.784-3.456-3.968-1.024-8.448-1.024h-1.28z" />
-                <path d="m169.22 0v-83.2h54.272v18.432h-32.256v15.872h27.648v18.432h-27.648v30.464z" />
-            </g>
-        </svg>
-    );
-}
-
-export function Word({ className }: { className?: string }) {
-    const classes = className ?? "w-6 h-6 text-muted-foreground inline-flex mr-1";
-    return (
-        <svg
-            className={`${classes}`}
-            xmlns="http://www.w3.org/2000/svg"
-            fill="#FFF"
-            stroke-miterlimit="10"
-            strokeWidth="2"
-            viewBox="0 0 96 96"
-        >
-            <path
-                stroke="#979593"
-                d="M67.1716 7H27c-1.1046 0-2 .8954-2 2v78c0 1.1046.8954 2 2 2h58c1.1046 0 2-.8954 2-2V26.8284c0-.5304-.2107-1.0391-.5858-1.4142L68.5858 7.5858C68.2107 7.2107 67.702 7 67.1716 7z"
-            />
-            <path fill="none" stroke="#979593" d="M67 7v18c0 1.1046.8954 2 2 2h18" />
-            <path
-                fill="#C8C6C4"
-                d="M79 61H48v-2h31c.5523 0 1 .4477 1 1s-.4477 1-1 1zm0-6H48v-2h31c.5523 0 1 .4477 1 1s-.4477 1-1 1zm0-6H48v-2h31c.5523 0 1 .4477 1 1s-.4477 1-1 1zm0-6H48v-2h31c.5523 0 1 .4477 1 1s-.4477 1-1 1zm0 24H48v-2h31c.5523 0 1 .4477 1 1s-.4477 1-1 1z"
-            />
-            <path
-                fill="#185ABD"
-                d="M12 74h32c2.2091 0 4-1.7909 4-4V38c0-2.2091-1.7909-4-4-4H12c-2.2091 0-4 1.7909-4 4v32c0 2.2091 1.7909 4 4 4z"
-            />
-            <path d="M21.6245 60.6455c.0661.522.109.9769.1296 1.3657h.0762c.0306-.3685.0889-.8129.1751-1.3349.0862-.5211.1703-.961.2517-1.319L25.7911 44h4.5702l3.6562 15.1272c.183.7468.3353 1.6973.457 2.8532h.0608c.0508-.7979.1777-1.7184.3809-2.7615L37.8413 44H42l-5.1183 22h-4.86l-3.4885-14.5744c-.1016-.4197-.2158-.9663-.3428-1.6417-.127-.6745-.2057-1.1656-.236-1.4724h-.0608c-.0407.358-.1195.8896-.2364 1.595-.1169.7062-.211 1.2273-.2819 1.565L24.1 66h-4.9357L14 44h4.2349l3.1843 15.3882c.0709.3165.1392.7362.2053 1.2573z" />
-        </svg>
-    );
-}
diff --git a/src/interface/web/app/page.tsx b/src/interface/web/app/page.tsx
index 532b4420..98d3a47e 100644
--- a/src/interface/web/app/page.tsx
+++ b/src/interface/web/app/page.tsx
@@ -11,7 +11,11 @@ import { Card, CardTitle } from "@/components/ui/card";
 import SuggestionCard from "@/app/components/suggestions/suggestionCard";
 import SidePanel from "@/app/components/sidePanel/chatHistorySidePanel";
 import Loading from "@/app/components/loading/loading";
-import { ChatInputArea, ChatOptions } from "@/app/components/chatInputArea/chatInputArea";
+import {
+    AttachedFileText,
+    ChatInputArea,
+    ChatOptions,
+} from "@/app/components/chatInputArea/chatInputArea";
 import { Suggestion, suggestionsData } from "@/app/components/suggestions/suggestionsData";
 import LoginPrompt from "@/app/components/loginPrompt/loginPrompt";
 
@@ -34,7 +38,7 @@ import { Popover, PopoverContent, PopoverTrigger } from "@/components/ui/popover
 interface ChatBodyDataProps {
     chatOptionsData: ChatOptions | null;
     onConversationIdChange?: (conversationId: string) => void;
-    setUploadedFiles: (files: string[]) => void;
+    setUploadedFiles: (files: AttachedFileText[]) => void;
     isMobileWidth?: boolean;
     isLoggedIn: boolean;
     userConfig: UserConfig | null;
@@ -155,6 +159,7 @@ function ChatBodyData(props: ChatBodyDataProps) {
                     if (images.length > 0) {
                         localStorage.setItem("images", JSON.stringify(images));
                     }
+
                     window.location.href = `/chat?conversationId=${newConversationId}`;
                 } catch (error) {
                     console.error("Error creating new conversation:", error);
@@ -401,7 +406,7 @@ export default function Home() {
     const [chatOptionsData, setChatOptionsData] = useState<ChatOptions | null>(null);
     const [isLoading, setLoading] = useState(true);
     const [conversationId, setConversationID] = useState<string | null>(null);
-    const [uploadedFiles, setUploadedFiles] = useState<string[]>([]);
+    const [uploadedFiles, setUploadedFiles] = useState<AttachedFileText[] | null>(null);
     const isMobileWidth = useIsMobileWidth();
 
     const { userConfig: initialUserConfig, isLoadingUserConfig } = useUserConfig(true);
@@ -417,6 +422,12 @@ export default function Home() {
         setUserConfig(initialUserConfig);
     }, [initialUserConfig]);
 
+    useEffect(() => {
+        if (uploadedFiles) {
+            localStorage.setItem("uploadedFiles", JSON.stringify(uploadedFiles));
+        }
+    }, [uploadedFiles]);
+
     useEffect(() => {
         fetch("/api/chat/options")
             .then((response) => response.json())
@@ -442,7 +453,7 @@ export default function Home() {
             <div className={`${styles.sidePanel}`}>
                 <SidePanel
                     conversationId={conversationId}
-                    uploadedFiles={uploadedFiles}
+                    uploadedFiles={[]}
                     isMobileWidth={isMobileWidth}
                 />
             </div>
diff --git a/src/interface/web/app/settings/page.tsx b/src/interface/web/app/settings/page.tsx
index fe3e11e7..bab7df32 100644
--- a/src/interface/web/app/settings/page.tsx
+++ b/src/interface/web/app/settings/page.tsx
@@ -137,10 +137,8 @@ const ManageFilesModal: React.FC<{ onClose: () => void }> = ({ onClose }) => {
 
     const deleteSelected = async () => {
         let filesToDelete = selectedFiles.length > 0 ? selectedFiles : filteredFiles;
-        console.log("Delete selected files", filesToDelete);
 
         if (filesToDelete.length === 0) {
-            console.log("No files to delete");
             return;
         }
 
@@ -162,15 +160,12 @@ const ManageFilesModal: React.FC<{ onClose: () => void }> = ({ onClose }) => {
 
             // Reset selectedFiles
             setSelectedFiles([]);
-
-            console.log("Deleted files:", filesToDelete);
         } catch (error) {
             console.error("Error deleting files:", error);
         }
     };
 
     const deleteFile = async (filename: string) => {
-        console.log("Delete selected file", filename);
         try {
             const response = await fetch(
                 `/api/content/file?filename=${encodeURIComponent(filename)}`,
@@ -189,8 +184,6 @@ const ManageFilesModal: React.FC<{ onClose: () => void }> = ({ onClose }) => {
 
             // Remove the file from selectedFiles if it's there
             setSelectedFiles((prevSelected) => prevSelected.filter((file) => file !== filename));
-
-            console.log("Deleted file:", filename);
         } catch (error) {
             console.error("Error deleting file:", error);
         }
diff --git a/src/interface/web/app/share/chat/page.tsx b/src/interface/web/app/share/chat/page.tsx
index a7e66940..2a956083 100644
--- a/src/interface/web/app/share/chat/page.tsx
+++ b/src/interface/web/app/share/chat/page.tsx
@@ -5,23 +5,25 @@ import React, { Suspense, useEffect, useRef, useState } from "react";
 
 import SidePanel from "../../components/sidePanel/chatHistorySidePanel";
 import ChatHistory from "../../components/chatHistory/chatHistory";
-import NavMenu from "../../components/navMenu/navMenu";
 import Loading from "../../components/loading/loading";
 
 import "katex/dist/katex.min.css";
 
-import { useIPLocationData, useIsMobileWidth, welcomeConsole } from "../../common/utils";
+import { useIsMobileWidth, welcomeConsole } from "../../common/utils";
 import { useAuthenticatedData } from "@/app/common/auth";
 
-import { ChatInputArea, ChatOptions } from "@/app/components/chatInputArea/chatInputArea";
+import {
+    AttachedFileText,
+    ChatInputArea,
+    ChatOptions,
+} from "@/app/components/chatInputArea/chatInputArea";
 import { StreamMessage } from "@/app/components/chatMessage/chatMessage";
-import { processMessageChunk } from "@/app/common/chatFunctions";
 import { AgentData } from "@/app/agents/page";
 
 interface ChatBodyDataProps {
     chatOptionsData: ChatOptions | null;
     setTitle: (title: string) => void;
-    setUploadedFiles: (files: string[]) => void;
+    setUploadedFiles: (files: AttachedFileText[]) => void;
     isMobileWidth?: boolean;
     publicConversationSlug: string;
     streamedMessages: StreamMessage[];
@@ -50,23 +52,6 @@ function ChatBodyData(props: ChatBodyDataProps) {
         }
     }, [images, props.setImages]);
 
-    useEffect(() => {
-        const storedImages = localStorage.getItem("images");
-        if (storedImages) {
-            const parsedImages: string[] = JSON.parse(storedImages);
-            setImages(parsedImages);
-            const encodedImages = parsedImages.map((img: string) => encodeURIComponent(img));
-            props.setImages(encodedImages);
-            localStorage.removeItem("images");
-        }
-
-        const storedMessage = localStorage.getItem("message");
-        if (storedMessage) {
-            setProcessingMessage(true);
-            setQueryToProcess(storedMessage);
-        }
-    }, [setQueryToProcess, props.setImages]);
-
     useEffect(() => {
         if (message) {
             setProcessingMessage(true);
@@ -130,14 +115,10 @@ export default function SharedChat() {
     const [conversationId, setConversationID] = useState<string | undefined>(undefined);
     const [messages, setMessages] = useState<StreamMessage[]>([]);
     const [queryToProcess, setQueryToProcess] = useState<string>("");
-    const [processQuerySignal, setProcessQuerySignal] = useState(false);
-    const [uploadedFiles, setUploadedFiles] = useState<string[]>([]);
+    const [uploadedFiles, setUploadedFiles] = useState<AttachedFileText[] | null>(null);
     const [paramSlug, setParamSlug] = useState<string | undefined>(undefined);
     const [images, setImages] = useState<string[]>([]);
 
-    const locationData = useIPLocationData() || {
-        timezone: Intl.DateTimeFormat().resolvedOptions().timeZone,
-    };
     const authenticatedData = useAuthenticatedData();
     const isMobileWidth = useIsMobileWidth();
 
@@ -161,6 +142,12 @@ export default function SharedChat() {
         setParamSlug(window.location.pathname.split("/").pop() || "");
     }, []);
 
+    useEffect(() => {
+        if (uploadedFiles) {
+            localStorage.setItem("uploadedFiles", JSON.stringify(uploadedFiles));
+        }
+    }, [uploadedFiles]);
+
     useEffect(() => {
         if (queryToProcess && !conversationId) {
             // If the user has not yet started conversing in the chat, create a new conversation
@@ -173,6 +160,11 @@ export default function SharedChat() {
                 .then((response) => response.json())
                 .then((data) => {
                     setConversationID(data.conversation_id);
+                    localStorage.setItem("message", queryToProcess);
+                    if (images.length > 0) {
+                        localStorage.setItem("images", JSON.stringify(images));
+                    }
+                    window.location.href = `/chat?conversationId=${data.conversation_id}`;
                 })
                 .catch((err) => {
                     console.error(err);
@@ -180,105 +172,8 @@ export default function SharedChat() {
                 });
             return;
         }
-
-        if (queryToProcess) {
-            // Add a new object to the state
-            const newStreamMessage: StreamMessage = {
-                rawResponse: "",
-                trainOfThought: [],
-                context: [],
-                onlineContext: {},
-                codeContext: {},
-                completed: false,
-                timestamp: new Date().toISOString(),
-                rawQuery: queryToProcess || "",
-                images: images,
-            };
-            setMessages((prevMessages) => [...prevMessages, newStreamMessage]);
-            setProcessQuerySignal(true);
-        }
     }, [queryToProcess, conversationId, paramSlug]);
 
-    useEffect(() => {
-        if (processQuerySignal) {
-            chat();
-        }
-    }, [processQuerySignal]);
-
-    async function readChatStream(response: Response) {
-        if (!response.ok) throw new Error(response.statusText);
-        if (!response.body) throw new Error("Response body is null");
-
-        const reader = response.body.getReader();
-        const decoder = new TextDecoder();
-        const eventDelimiter = "␃🔚␗";
-        let buffer = "";
-
-        while (true) {
-            const { done, value } = await reader.read();
-            if (done) {
-                setQueryToProcess("");
-                setProcessQuerySignal(false);
-                setImages([]);
-                break;
-            }
-
-            const chunk = decoder.decode(value, { stream: true });
-
-            buffer += chunk;
-
-            let newEventIndex;
-            while ((newEventIndex = buffer.indexOf(eventDelimiter)) !== -1) {
-                const event = buffer.slice(0, newEventIndex);
-                buffer = buffer.slice(newEventIndex + eventDelimiter.length);
-                if (event) {
-                    const currentMessage = messages.find((message) => !message.completed);
-
-                    if (!currentMessage) {
-                        console.error("No current message found");
-                        return;
-                    }
-
-                    processMessageChunk(event, currentMessage);
-
-                    setMessages([...messages]);
-                }
-            }
-        }
-    }
-
-    async function chat() {
-        if (!queryToProcess || !conversationId) return;
-        const chatAPI = "/api/chat?client=web";
-        const chatAPIBody = {
-            q: queryToProcess,
-            conversation_id: conversationId,
-            stream: true,
-            ...(locationData && {
-                region: locationData.region,
-                country: locationData.country,
-                city: locationData.city,
-                country_code: locationData.countryCode,
-                timezone: locationData.timezone,
-            }),
-            ...(images.length > 0 && { image: images }),
-        };
-
-        const response = await fetch(chatAPI, {
-            method: "POST",
-            headers: {
-                "Content-Type": "application/json",
-            },
-            body: JSON.stringify(chatAPIBody),
-        });
-
-        try {
-            await readChatStream(response);
-        } catch (error) {
-            console.error(error);
-        }
-    }
-
     if (isLoading) {
         return <Loading />;
     }
@@ -293,7 +188,7 @@ export default function SharedChat() {
             <div className={styles.sidePanel}>
                 <SidePanel
                     conversationId={conversationId ?? null}
-                    uploadedFiles={uploadedFiles}
+                    uploadedFiles={[]}
                     isMobileWidth={isMobileWidth}
                 />
             </div>
diff --git a/src/interface/web/components/ui/textarea.tsx b/src/interface/web/components/ui/textarea.tsx
index 68aefb3e..ce071877 100644
--- a/src/interface/web/components/ui/textarea.tsx
+++ b/src/interface/web/components/ui/textarea.tsx
@@ -9,7 +9,7 @@ const Textarea = React.forwardRef<HTMLTextAreaElement, TextareaProps>(
         return (
             <textarea
                 className={cn(
-                    "flex min-h-[80px] w-full rounded-md border border-input bg-background px-3 py-2 text-sm ring-offset-background placeholder:text-muted-foreground focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-ring focus-visible:ring-offset-2 disabled:cursor-not-allowed disabled:opacity-50",
+                    "flex min-h-[80px] w-full rounded-md border border-input bg-background px-3 py-2 text-sm ring-offset-background placeholder:text-muted-foreground disabled:cursor-not-allowed disabled:opacity-50",
                     className,
                 )}
                 ref={ref}
diff --git a/src/khoj/database/adapters/__init__.py b/src/khoj/database/adapters/__init__.py
index fbb00690..6676eefa 100644
--- a/src/khoj/database/adapters/__init__.py
+++ b/src/khoj/database/adapters/__init__.py
@@ -1387,6 +1387,10 @@ class FileObjectAdapters:
     async def async_get_file_objects_by_name(user: KhojUser, file_name: str, agent: Agent = None):
         return await sync_to_async(list)(FileObject.objects.filter(user=user, file_name=file_name, agent=agent))
 
+    @staticmethod
+    async def async_get_file_objects_by_names(user: KhojUser, file_names: List[str]):
+        return await sync_to_async(list)(FileObject.objects.filter(user=user, file_name__in=file_names))
+
     @staticmethod
     async def async_get_all_file_objects(user: KhojUser):
         return await sync_to_async(list)(FileObject.objects.filter(user=user))
diff --git a/src/khoj/database/models/__init__.py b/src/khoj/database/models/__init__.py
index 477690cb..bcd8d376 100644
--- a/src/khoj/database/models/__init__.py
+++ b/src/khoj/database/models/__init__.py
@@ -458,7 +458,11 @@ class Conversation(BaseModel):
     user = models.ForeignKey(KhojUser, on_delete=models.CASCADE)
     conversation_log = models.JSONField(default=dict)
     client = models.ForeignKey(ClientApplication, on_delete=models.CASCADE, default=None, null=True, blank=True)
+
+    # Slug is an app-generated conversation identifier. Need not be unique. Used as display title essentially.
     slug = models.CharField(max_length=200, default=None, null=True, blank=True)
+
+    # The title field is explicitly set by the user.
     title = models.CharField(max_length=200, default=None, null=True, blank=True)
     agent = models.ForeignKey(Agent, on_delete=models.SET_NULL, default=None, null=True, blank=True)
     file_filters = models.JSONField(default=list)
diff --git a/src/khoj/processor/content/docx/docx_to_entries.py b/src/khoj/processor/content/docx/docx_to_entries.py
index 00ed3ca4..19d9ba13 100644
--- a/src/khoj/processor/content/docx/docx_to_entries.py
+++ b/src/khoj/processor/content/docx/docx_to_entries.py
@@ -1,6 +1,5 @@
 import logging
-import os
-from datetime import datetime
+import tempfile
 from typing import Dict, List, Tuple
 
 from langchain_community.document_loaders import Docx2txtLoader
@@ -58,28 +57,13 @@ class DocxToEntries(TextToEntries):
         file_to_text_map = dict()
         for docx_file in docx_files:
             try:
-                timestamp_now = datetime.utcnow().timestamp()
-                tmp_file = f"tmp_docx_file_{timestamp_now}.docx"
-                with open(tmp_file, "wb") as f:
-                    bytes_content = docx_files[docx_file]
-                    f.write(bytes_content)
-
-                # Load the content using Docx2txtLoader
-                loader = Docx2txtLoader(tmp_file)
-                docx_entries_per_file = loader.load()
-
-                # Convert the loaded entries into the desired format
-                docx_texts = [page.page_content for page in docx_entries_per_file]
-
+                docx_texts = DocxToEntries.extract_text(docx_files[docx_file])
                 entry_to_location_map += zip(docx_texts, [docx_file] * len(docx_texts))
                 entries.extend(docx_texts)
                 file_to_text_map[docx_file] = docx_texts
             except Exception as e:
-                logger.warning(f"Unable to process file: {docx_file}. This file will not be indexed.")
+                logger.warning(f"Unable to extract entries from file: {docx_file}")
                 logger.warning(e, exc_info=True)
-            finally:
-                if os.path.exists(f"{tmp_file}"):
-                    os.remove(f"{tmp_file}")
         return file_to_text_map, DocxToEntries.convert_docx_entries_to_maps(entries, dict(entry_to_location_map))
 
     @staticmethod
@@ -103,3 +87,25 @@ class DocxToEntries(TextToEntries):
         logger.debug(f"Converted {len(parsed_entries)} DOCX entries to dictionaries")
 
         return entries
+
+    @staticmethod
+    def extract_text(docx_file):
+        """Extract text from specified DOCX file"""
+        try:
+            docx_entry_by_pages = []
+            # Create temp file with .docx extension that gets auto-deleted
+            with tempfile.NamedTemporaryFile(suffix=".docx", delete=True) as tmp:
+                tmp.write(docx_file)
+                tmp.flush()  # Ensure all data is written
+
+                # Load the content using Docx2txtLoader
+                loader = Docx2txtLoader(tmp.name)
+                docx_entries_per_file = loader.load()
+
+                # Convert the loaded entries into the desired format
+                docx_entry_by_pages = [page.page_content for page in docx_entries_per_file]
+        except Exception as e:
+            logger.warning(f"Unable to extract text from file: {docx_file}")
+            logger.warning(e, exc_info=True)
+
+        return docx_entry_by_pages
diff --git a/src/khoj/processor/content/pdf/pdf_to_entries.py b/src/khoj/processor/content/pdf/pdf_to_entries.py
index 063d1e74..f1ac5104 100644
--- a/src/khoj/processor/content/pdf/pdf_to_entries.py
+++ b/src/khoj/processor/content/pdf/pdf_to_entries.py
@@ -1,13 +1,10 @@
-import base64
 import logging
-import os
-from datetime import datetime
+import tempfile
+from io import BytesIO
 from typing import Dict, List, Tuple
 
 from langchain_community.document_loaders import PyMuPDFLoader
 
-# importing FileObjectAdapter so that we can add new files and debug file object db.
-# from khoj.database.adapters import FileObjectAdapters
 from khoj.database.models import Entry as DbEntry
 from khoj.database.models import KhojUser
 from khoj.processor.content.text_to_entries import TextToEntries
@@ -60,31 +57,13 @@ class PdfToEntries(TextToEntries):
         entry_to_location_map: List[Tuple[str, str]] = []
         for pdf_file in pdf_files:
             try:
-                # Write the PDF file to a temporary file, as it is stored in byte format in the pdf_file object and the PDF Loader expects a file path
-                timestamp_now = datetime.utcnow().timestamp()
-                tmp_file = f"tmp_pdf_file_{timestamp_now}.pdf"
-                with open(f"{tmp_file}", "wb") as f:
-                    bytes = pdf_files[pdf_file]
-                    f.write(bytes)
-                try:
-                    loader = PyMuPDFLoader(f"{tmp_file}", extract_images=False)
-                    pdf_entries_per_file = [page.page_content for page in loader.load()]
-                except ImportError:
-                    loader = PyMuPDFLoader(f"{tmp_file}")
-                    pdf_entries_per_file = [
-                        page.page_content for page in loader.load()
-                    ]  # page_content items list for a given pdf.
-                entry_to_location_map += zip(
-                    pdf_entries_per_file, [pdf_file] * len(pdf_entries_per_file)
-                )  # this is an indexed map of pdf_entries for the pdf.
+                pdf_entries_per_file = PdfToEntries.extract_text(pdf_files[pdf_file])
+                entry_to_location_map += zip(pdf_entries_per_file, [pdf_file] * len(pdf_entries_per_file))
                 entries.extend(pdf_entries_per_file)
                 file_to_text_map[pdf_file] = pdf_entries_per_file
             except Exception as e:
-                logger.warning(f"Unable to process file: {pdf_file}. This file will not be indexed.")
+                logger.warning(f"Unable to extract entries from file: {pdf_file}")
                 logger.warning(e, exc_info=True)
-            finally:
-                if os.path.exists(f"{tmp_file}"):
-                    os.remove(f"{tmp_file}")
 
         return file_to_text_map, PdfToEntries.convert_pdf_entries_to_maps(entries, dict(entry_to_location_map))
 
@@ -109,3 +88,32 @@ class PdfToEntries(TextToEntries):
         logger.debug(f"Converted {len(parsed_entries)} PDF entries to dictionaries")
 
         return entries
+
+    @staticmethod
+    def extract_text(pdf_file):
+        """Extract text from specified PDF files"""
+        try:
+            # Create temp file with .pdf extension that gets auto-deleted
+            with tempfile.NamedTemporaryFile(suffix=".pdf", delete=True) as tmpf:
+                tmpf.write(pdf_file)
+                tmpf.flush()  # Ensure all data is written
+
+                # Load the content using PyMuPDFLoader
+                loader = PyMuPDFLoader(tmpf.name, extract_images=True)
+                pdf_entries_per_file = loader.load()
+
+                # Convert the loaded entries into the desired format
+                pdf_entry_by_pages = [PdfToEntries.clean_text(page.page_content) for page in pdf_entries_per_file]
+        except Exception as e:
+            logger.warning(f"Unable to process file: {pdf_file}. This file will not be indexed.")
+            logger.warning(e, exc_info=True)
+
+        return pdf_entry_by_pages
+
+    @staticmethod
+    def clean_text(text: str) -> str:
+        # Remove null bytes
+        text = text.replace("\x00", "")
+        # Replace invalid Unicode
+        text = text.encode("utf-8", errors="ignore").decode("utf-8")
+        return text
diff --git a/src/khoj/processor/conversation/anthropic/anthropic_chat.py b/src/khoj/processor/conversation/anthropic/anthropic_chat.py
index e878ceea..c934292a 100644
--- a/src/khoj/processor/conversation/anthropic/anthropic_chat.py
+++ b/src/khoj/processor/conversation/anthropic/anthropic_chat.py
@@ -36,6 +36,7 @@ def extract_questions_anthropic(
     query_images: Optional[list[str]] = None,
     vision_enabled: bool = False,
     personality_context: Optional[str] = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     """
@@ -82,9 +83,12 @@ def extract_questions_anthropic(
         images=query_images,
         model_type=ChatModelOptions.ModelType.ANTHROPIC,
         vision_enabled=vision_enabled,
+        attached_file_context=query_files,
     )
 
-    messages = [ChatMessage(content=prompt, role="user")]
+    messages = []
+
+    messages.append(ChatMessage(content=prompt, role="user"))
 
     messages, system_prompt = format_messages_for_anthropic(messages, system_prompt)
 
@@ -148,6 +152,7 @@ def converse_anthropic(
     agent: Agent = None,
     query_images: Optional[list[str]] = None,
     vision_available: bool = False,
+    query_files: str = None,
     tracer: dict = {},
 ):
     """
@@ -205,6 +210,7 @@ def converse_anthropic(
         query_images=query_images,
         vision_enabled=vision_available,
         model_type=ChatModelOptions.ModelType.ANTHROPIC,
+        query_files=query_files,
     )
 
     messages, system_prompt = format_messages_for_anthropic(messages, system_prompt)
diff --git a/src/khoj/processor/conversation/google/gemini_chat.py b/src/khoj/processor/conversation/google/gemini_chat.py
index aebda1a8..db6f3c4e 100644
--- a/src/khoj/processor/conversation/google/gemini_chat.py
+++ b/src/khoj/processor/conversation/google/gemini_chat.py
@@ -37,6 +37,7 @@ def extract_questions_gemini(
     query_images: Optional[list[str]] = None,
     vision_enabled: bool = False,
     personality_context: Optional[str] = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     """
@@ -83,9 +84,13 @@ def extract_questions_gemini(
         images=query_images,
         model_type=ChatModelOptions.ModelType.GOOGLE,
         vision_enabled=vision_enabled,
+        attached_file_context=query_files,
     )
 
-    messages = [ChatMessage(content=prompt, role="user"), ChatMessage(content=system_prompt, role="system")]
+    messages = []
+
+    messages.append(ChatMessage(content=prompt, role="user"))
+    messages.append(ChatMessage(content=system_prompt, role="system"))
 
     response = gemini_send_message_to_model(
         messages, api_key, model, response_type="json_object", temperature=temperature, tracer=tracer
@@ -108,7 +113,13 @@ def extract_questions_gemini(
 
 
 def gemini_send_message_to_model(
-    messages, api_key, model, response_type="text", temperature=0, model_kwargs=None, tracer={}
+    messages,
+    api_key,
+    model,
+    response_type="text",
+    temperature=0,
+    model_kwargs=None,
+    tracer={},
 ):
     """
     Send message to model
@@ -151,6 +162,7 @@ def converse_gemini(
     agent: Agent = None,
     query_images: Optional[list[str]] = None,
     vision_available: bool = False,
+    query_files: str = None,
     tracer={},
 ):
     """
@@ -209,6 +221,7 @@ def converse_gemini(
         query_images=query_images,
         vision_enabled=vision_available,
         model_type=ChatModelOptions.ModelType.GOOGLE,
+        query_files=query_files,
     )
 
     messages, system_prompt = format_messages_for_gemini(messages, system_prompt)
diff --git a/src/khoj/processor/conversation/offline/chat_model.py b/src/khoj/processor/conversation/offline/chat_model.py
index aaaaa081..c41c847b 100644
--- a/src/khoj/processor/conversation/offline/chat_model.py
+++ b/src/khoj/processor/conversation/offline/chat_model.py
@@ -37,6 +37,7 @@ def extract_questions_offline(
     max_prompt_size: int = None,
     temperature: float = 0.7,
     personality_context: Optional[str] = None,
+    query_files: str = None,
     tracer: dict = {},
 ) -> List[str]:
     """
@@ -87,6 +88,7 @@ def extract_questions_offline(
         loaded_model=offline_chat_model,
         max_prompt_size=max_prompt_size,
         model_type=ChatModelOptions.ModelType.OFFLINE,
+        query_files=query_files,
     )
 
     state.chat_lock.acquire()
@@ -152,6 +154,7 @@ def converse_offline(
     location_data: LocationData = None,
     user_name: str = None,
     agent: Agent = None,
+    query_files: str = None,
     tracer: dict = {},
 ) -> Union[ThreadedGenerator, Iterator[str]]:
     """
@@ -216,6 +219,7 @@ def converse_offline(
         max_prompt_size=max_prompt_size,
         tokenizer_name=tokenizer_name,
         model_type=ChatModelOptions.ModelType.OFFLINE,
+        query_files=query_files,
     )
 
     truncated_messages = "\n".join({f"{message.content[:70]}..." for message in messages})
diff --git a/src/khoj/processor/conversation/openai/gpt.py b/src/khoj/processor/conversation/openai/gpt.py
index c376a90e..c4cb0c67 100644
--- a/src/khoj/processor/conversation/openai/gpt.py
+++ b/src/khoj/processor/conversation/openai/gpt.py
@@ -34,6 +34,7 @@ def extract_questions(
     query_images: Optional[list[str]] = None,
     vision_enabled: bool = False,
     personality_context: Optional[str] = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     """
@@ -79,9 +80,11 @@ def extract_questions(
         images=query_images,
         model_type=ChatModelOptions.ModelType.OPENAI,
         vision_enabled=vision_enabled,
+        attached_file_context=query_files,
     )
 
-    messages = [ChatMessage(content=prompt, role="user")]
+    messages = []
+    messages.append(ChatMessage(content=prompt, role="user"))
 
     response = send_message_to_model(
         messages,
@@ -148,6 +151,7 @@ def converse(
     agent: Agent = None,
     query_images: Optional[list[str]] = None,
     vision_available: bool = False,
+    query_files: str = None,
     tracer: dict = {},
 ):
     """
@@ -206,6 +210,7 @@ def converse(
         query_images=query_images,
         vision_enabled=vision_available,
         model_type=ChatModelOptions.ModelType.OPENAI,
+        query_files=query_files,
     )
     truncated_messages = "\n".join({f"{message.content[:70]}..." for message in messages})
     logger.debug(f"Conversation Context for GPT: {truncated_messages}")
diff --git a/src/khoj/processor/conversation/prompts.py b/src/khoj/processor/conversation/prompts.py
index 864b864e..4ff8aa9c 100644
--- a/src/khoj/processor/conversation/prompts.py
+++ b/src/khoj/processor/conversation/prompts.py
@@ -988,16 +988,27 @@ You are an extremely smart and helpful title generator assistant. Given a user q
 
 # Examples:
 User: Show a new Calvin and Hobbes quote every morning at 9am. My Current Location: Shanghai, China
-Khoj: Your daily Calvin and Hobbes Quote
+Assistant: Your daily Calvin and Hobbes Quote
 
 User: Notify me when version 2.0.0 of the sentence transformers python package is released. My Current Location: Mexico City, Mexico
-Khoj: Sentence Transformers Python Package Version 2.0.0 Release
+Assistant: Sentence Transformers Python Package Version 2.0.0 Release
 
 User: Gather the latest tech news on the first sunday of every month.
-Khoj: Your Monthly Dose of Tech News
+Assistant: Your Monthly Dose of Tech News
 
 User Query: {query}
-Khoj:
+Assistant:
+""".strip()
+)
+
+conversation_title_generation = PromptTemplate.from_template(
+    """
+You are an extremely smart and helpful title generator assistant. Given a conversation, extract the subject of the conversation. Crisp, informative, ten words or less.
+
+Conversation History:
+{chat_history}
+
+Assistant:
 """.strip()
 )
 
diff --git a/src/khoj/processor/conversation/utils.py b/src/khoj/processor/conversation/utils.py
index 1f43aa80..dd43a785 100644
--- a/src/khoj/processor/conversation/utils.py
+++ b/src/khoj/processor/conversation/utils.py
@@ -36,6 +36,7 @@ from khoj.utils.helpers import (
     is_none_or_empty,
     merge_dicts,
 )
+from khoj.utils.rawconfig import FileAttachment
 
 logger = logging.getLogger(__name__)
 
@@ -146,7 +147,7 @@ def construct_chat_history(conversation_history: dict, n: int = 4, agent_name="A
             chat_history += f"User: {chat['intent']['query']}\n"
 
             if chat["intent"].get("inferred-queries"):
-                chat_history += f'Khoj: {{"queries": {chat["intent"].get("inferred-queries")}}}\n'
+                chat_history += f'{agent_name}: {{"queries": {chat["intent"].get("inferred-queries")}}}\n'
 
             chat_history += f"{agent_name}: {chat['message']}\n\n"
         elif chat["by"] == "khoj" and ("text-to-image" in chat["intent"].get("type")):
@@ -155,6 +156,16 @@ def construct_chat_history(conversation_history: dict, n: int = 4, agent_name="A
         elif chat["by"] == "khoj" and ("excalidraw" in chat["intent"].get("type")):
             chat_history += f"User: {chat['intent']['query']}\n"
             chat_history += f"{agent_name}: {chat['intent']['inferred-queries'][0]}\n"
+        elif chat["by"] == "you":
+            raw_query_files = chat.get("queryFiles")
+            if raw_query_files:
+                query_files: Dict[str, str] = {}
+                for file in raw_query_files:
+                    query_files[file["name"]] = file["content"]
+
+                query_file_context = gather_raw_query_files(query_files)
+                chat_history += f"User: {query_file_context}\n"
+
     return chat_history
 
 
@@ -243,8 +254,9 @@ def save_to_conversation_log(
     conversation_id: str = None,
     automation_id: str = None,
     query_images: List[str] = None,
-    tracer: Dict[str, Any] = {},
+    raw_query_files: List[FileAttachment] = [],
     train_of_thought: List[Any] = [],
+    tracer: Dict[str, Any] = {},
 ):
     user_message_time = user_message_time or datetime.now().strftime("%Y-%m-%d %H:%M:%S")
     turn_id = tracer.get("mid") or str(uuid.uuid4())
@@ -255,6 +267,7 @@ def save_to_conversation_log(
             "created": user_message_time,
             "images": query_images,
             "turnId": turn_id,
+            "queryFiles": [file.model_dump(mode="json") for file in raw_query_files],
         },
         khoj_message_metadata={
             "context": compiled_references,
@@ -289,25 +302,50 @@ Khoj: "{inferred_queries if ("text-to-image" in intent_type) else chat_response}
     )
 
 
-def construct_structured_message(message: str, images: list[str], model_type: str, vision_enabled: bool):
+def construct_structured_message(
+    message: str, images: list[str], model_type: str, vision_enabled: bool, attached_file_context: str
+):
     """
     Format messages into appropriate multimedia format for supported chat model types
     """
-    if not images or not vision_enabled:
-        return message
-
     if model_type in [
         ChatModelOptions.ModelType.OPENAI,
         ChatModelOptions.ModelType.GOOGLE,
         ChatModelOptions.ModelType.ANTHROPIC,
     ]:
-        return [
+        constructed_messages: List[Any] = [
             {"type": "text", "text": message},
-            *[{"type": "image_url", "image_url": {"url": image}} for image in images],
         ]
+
+        if not is_none_or_empty(attached_file_context):
+            constructed_messages.append({"type": "text", "text": attached_file_context})
+        if vision_enabled and images:
+            for image in images:
+                constructed_messages.append({"type": "image_url", "image_url": {"url": image}})
+        return constructed_messages
+
+    if not is_none_or_empty(attached_file_context):
+        return f"{attached_file_context}\n\n{message}"
+
     return message
 
 
+def gather_raw_query_files(
+    query_files: Dict[str, str],
+):
+    """
+    Gather contextual data from the given (raw) files
+    """
+
+    if len(query_files) == 0:
+        return ""
+
+    contextual_data = " ".join(
+        [f"File: {file_name}\n\n{file_content}\n\n" for file_name, file_content in query_files.items()]
+    )
+    return f"I have attached the following files:\n\n{contextual_data}"
+
+
 def generate_chatml_messages_with_context(
     user_message,
     system_message=None,
@@ -320,6 +358,7 @@ def generate_chatml_messages_with_context(
     vision_enabled=False,
     model_type="",
     context_message="",
+    query_files: str = None,
 ):
     """Generate chat messages with appropriate context from previous conversation to send to the chat model"""
     # Set max prompt size from user config or based on pre-configured for model and machine specs
@@ -336,6 +375,8 @@ def generate_chatml_messages_with_context(
     chatml_messages: List[ChatMessage] = []
     for chat in conversation_log.get("chat", []):
         message_context = ""
+        message_attached_files = ""
+
         if chat["by"] == "khoj" and "excalidraw" in chat["intent"].get("type", ""):
             message_context += chat.get("intent").get("inferred-queries")[0]
         if not is_none_or_empty(chat.get("context")):
@@ -347,14 +388,27 @@ def generate_chatml_messages_with_context(
                 }
             )
             message_context += f"{prompts.notes_conversation.format(references=references)}\n\n"
+
+        if chat.get("queryFiles"):
+            raw_query_files = chat.get("queryFiles")
+            query_files_dict = dict()
+            for file in raw_query_files:
+                query_files_dict[file["name"]] = file["content"]
+
+            message_attached_files = gather_raw_query_files(query_files_dict)
+            chatml_messages.append(ChatMessage(content=message_attached_files, role="user"))
+
         if not is_none_or_empty(chat.get("onlineContext")):
             message_context += f"{prompts.online_search_conversation.format(online_results=chat.get('onlineContext'))}"
+
         if not is_none_or_empty(message_context):
             reconstructed_context_message = ChatMessage(content=message_context, role="user")
             chatml_messages.insert(0, reconstructed_context_message)
 
         role = "user" if chat["by"] == "you" else "assistant"
-        message_content = construct_structured_message(chat["message"], chat.get("images"), model_type, vision_enabled)
+        message_content = construct_structured_message(
+            chat["message"], chat.get("images"), model_type, vision_enabled, attached_file_context=query_files
+        )
 
         reconstructed_message = ChatMessage(content=message_content, role=role)
         chatml_messages.insert(0, reconstructed_message)
@@ -366,14 +420,18 @@ def generate_chatml_messages_with_context(
     if not is_none_or_empty(user_message):
         messages.append(
             ChatMessage(
-                content=construct_structured_message(user_message, query_images, model_type, vision_enabled),
+                content=construct_structured_message(
+                    user_message, query_images, model_type, vision_enabled, query_files
+                ),
                 role="user",
             )
         )
     if not is_none_or_empty(context_message):
         messages.append(ChatMessage(content=context_message, role="user"))
+
     if len(chatml_messages) > 0:
         messages += chatml_messages
+
     if not is_none_or_empty(system_message):
         messages.append(ChatMessage(content=system_message, role="system"))
 
diff --git a/src/khoj/processor/image/generate.py b/src/khoj/processor/image/generate.py
index bdc00e09..6c1f71b6 100644
--- a/src/khoj/processor/image/generate.py
+++ b/src/khoj/processor/image/generate.py
@@ -28,6 +28,7 @@ async def text_to_image(
     send_status_func: Optional[Callable] = None,
     query_images: Optional[List[str]] = None,
     agent: Agent = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     status_code = 200
@@ -69,6 +70,7 @@ async def text_to_image(
         query_images=query_images,
         user=user,
         agent=agent,
+        query_files=query_files,
         tracer=tracer,
     )
 
diff --git a/src/khoj/processor/tools/online_search.py b/src/khoj/processor/tools/online_search.py
index 2ee6e72c..7fdb82d4 100644
--- a/src/khoj/processor/tools/online_search.py
+++ b/src/khoj/processor/tools/online_search.py
@@ -68,6 +68,7 @@ async def search_online(
     query_images: List[str] = None,
     previous_subqueries: Set = set(),
     agent: Agent = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     query += " ".join(custom_filters)
@@ -78,7 +79,14 @@ async def search_online(
 
     # Breakdown the query into subqueries to get the correct answer
     new_subqueries = await generate_online_subqueries(
-        query, conversation_history, location, user, query_images=query_images, agent=agent, tracer=tracer
+        query,
+        conversation_history,
+        location,
+        user,
+        query_images=query_images,
+        agent=agent,
+        tracer=tracer,
+        query_files=query_files,
     )
     subqueries = list(new_subqueries - previous_subqueries)
     response_dict: Dict[str, Dict[str, List[Dict] | Dict]] = {}
@@ -169,13 +177,21 @@ async def read_webpages(
     send_status_func: Optional[Callable] = None,
     query_images: List[str] = None,
     agent: Agent = None,
-    tracer: dict = {},
     max_webpages_to_read: int = DEFAULT_MAX_WEBPAGES_TO_READ,
+    query_files: str = None,
+    tracer: dict = {},
 ):
     "Infer web pages to read from the query and extract relevant information from them"
     logger.info(f"Inferring web pages to read")
     urls = await infer_webpage_urls(
-        query, conversation_history, location, user, query_images, agent=agent, tracer=tracer
+        query,
+        conversation_history,
+        location,
+        user,
+        query_images,
+        agent=agent,
+        query_files=query_files,
+        tracer=tracer,
     )
 
     # Get the top 10 web pages to read
diff --git a/src/khoj/processor/tools/run_code.py b/src/khoj/processor/tools/run_code.py
index d4ba9af1..e24b3b53 100644
--- a/src/khoj/processor/tools/run_code.py
+++ b/src/khoj/processor/tools/run_code.py
@@ -36,6 +36,7 @@ async def run_code(
     query_images: List[str] = None,
     agent: Agent = None,
     sandbox_url: str = SANDBOX_URL,
+    query_files: str = None,
     tracer: dict = {},
 ):
     # Generate Code
@@ -53,6 +54,7 @@ async def run_code(
                 query_images,
                 agent,
                 tracer,
+                query_files,
             )
     except Exception as e:
         raise ValueError(f"Failed to generate code for {query} with error: {e}")
@@ -82,6 +84,7 @@ async def generate_python_code(
     query_images: List[str] = None,
     agent: Agent = None,
     tracer: dict = {},
+    query_files: str = None,
 ) -> List[str]:
     location = f"{location_data}" if location_data else "Unknown"
     username = prompts.user_name.format(name=user.get_full_name()) if user.get_full_name() else ""
@@ -109,6 +112,7 @@ async def generate_python_code(
         response_type="json_object",
         user=user,
         tracer=tracer,
+        query_files=query_files,
     )
 
     # Validate that the response is a non-empty, JSON-serializable list
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index 3eb2dea5..f66fbce8 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -351,6 +351,7 @@ async def extract_references_and_questions(
     query_images: Optional[List[str]] = None,
     previous_inferred_queries: Set = set(),
     agent: Agent = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     user = request.user.object if request.user.is_authenticated else None
@@ -425,6 +426,7 @@ async def extract_references_and_questions(
                 user=user,
                 max_prompt_size=conversation_config.max_prompt_size,
                 personality_context=personality_context,
+                query_files=query_files,
                 tracer=tracer,
             )
         elif conversation_config.model_type == ChatModelOptions.ModelType.OPENAI:
@@ -443,6 +445,7 @@ async def extract_references_and_questions(
                 query_images=query_images,
                 vision_enabled=vision_enabled,
                 personality_context=personality_context,
+                query_files=query_files,
                 tracer=tracer,
             )
         elif conversation_config.model_type == ChatModelOptions.ModelType.ANTHROPIC:
@@ -458,6 +461,7 @@ async def extract_references_and_questions(
                 user=user,
                 vision_enabled=vision_enabled,
                 personality_context=personality_context,
+                query_files=query_files,
                 tracer=tracer,
             )
         elif conversation_config.model_type == ChatModelOptions.ModelType.GOOGLE:
@@ -474,6 +478,7 @@ async def extract_references_and_questions(
                 user=user,
                 vision_enabled=vision_enabled,
                 personality_context=personality_context,
+                query_files=query_files,
                 tracer=tracer,
             )
 
diff --git a/src/khoj/routers/api_chat.py b/src/khoj/routers/api_chat.py
index 648fb8dd..33476a97 100644
--- a/src/khoj/routers/api_chat.py
+++ b/src/khoj/routers/api_chat.py
@@ -19,7 +19,6 @@ from khoj.database.adapters import (
     AgentAdapters,
     ConversationAdapters,
     EntryAdapters,
-    FileObjectAdapters,
     PublicConversationAdapters,
     aget_user_name,
 )
@@ -45,12 +44,13 @@ from khoj.routers.helpers import (
     ConversationCommandRateLimiter,
     DeleteMessageRequestBody,
     FeedbackData,
+    acreate_title_from_history,
     agenerate_chat_response,
     aget_relevant_information_sources,
     aget_relevant_output_modes,
     construct_automation_created_message,
     create_automation,
-    extract_relevant_info,
+    gather_raw_query_files,
     generate_excalidraw_diagram,
     generate_summary_from_files,
     get_conversation_command,
@@ -76,7 +76,12 @@ from khoj.utils.helpers import (
     get_device,
     is_none_or_empty,
 )
-from khoj.utils.rawconfig import FileFilterRequest, FilesFilterRequest, LocationData
+from khoj.utils.rawconfig import (
+    ChatRequestBody,
+    FileFilterRequest,
+    FilesFilterRequest,
+    LocationData,
+)
 
 # Initialize Router
 logger = logging.getLogger(__name__)
@@ -374,7 +379,7 @@ def fork_public_conversation(
             {
                 "status": "ok",
                 "next_url": redirect_uri,
-                "conversation_id": new_conversation.id,
+                "conversation_id": str(new_conversation.id),
             }
         ),
     )
@@ -530,6 +535,32 @@ async def set_conversation_title(
     )
 
 
+@api_chat.post("/title")
+@requires(["authenticated"])
+async def generate_chat_title(
+    request: Request,
+    common: CommonQueryParams,
+    conversation_id: str,
+):
+    user: KhojUser = request.user.object
+    conversation = await ConversationAdapters.aget_conversation_by_user(user=user, conversation_id=conversation_id)
+
+    # Conversation.title is explicitly set by the user. Do not override.
+    if conversation.title:
+        return {"status": "ok", "title": conversation.title}
+
+    if not conversation:
+        raise HTTPException(status_code=404, detail="Conversation not found")
+
+    new_title = await acreate_title_from_history(request.user.object, conversation=conversation)
+
+    conversation.slug = new_title
+
+    conversation.asave()
+
+    return {"status": "ok", "title": new_title}
+
+
 @api_chat.delete("/conversation/message", response_class=Response)
 @requires(["authenticated"])
 def delete_message(request: Request, delete_request: DeleteMessageRequestBody) -> Response:
@@ -571,6 +602,7 @@ async def chat(
     country_code = body.country_code or get_country_code_from_timezone(body.timezone)
     timezone = body.timezone
     raw_images = body.images
+    raw_query_files = body.files
 
     async def event_generator(q: str, images: list[str]):
         start_time = time.perf_counter()
@@ -582,6 +614,7 @@ async def chat(
         q = unquote(q)
         train_of_thought = []
         nonlocal conversation_id
+        nonlocal raw_query_files
 
         tracer: dict = {
             "mid": turn_id,
@@ -601,6 +634,11 @@ async def chat(
                 if uploaded_image:
                     uploaded_images.append(uploaded_image)
 
+        query_files: Dict[str, str] = {}
+        if raw_query_files:
+            for file in raw_query_files:
+                query_files[file.name] = file.content
+
         async def send_event(event_type: ChatEvent, data: str | dict):
             nonlocal connection_alive, ttft, train_of_thought
             if not connection_alive or await request.is_disconnected():
@@ -711,6 +749,8 @@ async def chat(
         ## Extract Document References
         compiled_references: List[Any] = []
         inferred_queries: List[Any] = []
+        file_filters = conversation.file_filters if conversation and conversation.file_filters else []
+        attached_file_context = gather_raw_query_files(query_files)
 
         if conversation_commands == [ConversationCommand.Default] or is_automated_task:
             conversation_commands = await aget_relevant_information_sources(
@@ -720,6 +760,7 @@ async def chat(
                 user=user,
                 query_images=uploaded_images,
                 agent=agent,
+                query_files=attached_file_context,
                 tracer=tracer,
             )
 
@@ -765,6 +806,7 @@ async def chat(
                 user_name=user_name,
                 location=location,
                 file_filters=conversation.file_filters if conversation else [],
+                query_files=attached_file_context,
                 tracer=tracer,
             ):
                 if isinstance(research_result, InformationCollectionIteration):
@@ -804,10 +846,6 @@ async def chat(
                 response_log = "No files selected for summarization. Please add files using the section on the left."
                 async for result in send_llm_response(response_log):
                     yield result
-            elif len(file_filters) > 1 and not agent_has_entries:
-                response_log = "Only one file can be selected for summarization."
-                async for result in send_llm_response(response_log):
-                    yield result
             else:
                 async for response in generate_summary_from_files(
                     q=q,
@@ -817,6 +855,7 @@ async def chat(
                     query_images=uploaded_images,
                     agent=agent,
                     send_status_func=partial(send_event, ChatEvent.STATUS),
+                    query_files=attached_file_context,
                     tracer=tracer,
                 ):
                     if isinstance(response, dict) and ChatEvent.STATUS in response:
@@ -837,8 +876,9 @@ async def chat(
                 client_application=request.user.client_app,
                 conversation_id=conversation_id,
                 query_images=uploaded_images,
-                tracer=tracer,
                 train_of_thought=train_of_thought,
+                raw_query_files=raw_query_files,
+                tracer=tracer,
             )
             return
 
@@ -882,8 +922,9 @@ async def chat(
                 inferred_queries=[query_to_run],
                 automation_id=automation.id,
                 query_images=uploaded_images,
-                tracer=tracer,
                 train_of_thought=train_of_thought,
+                raw_query_files=raw_query_files,
+                tracer=tracer,
             )
             async for result in send_llm_response(llm_response):
                 yield result
@@ -905,6 +946,7 @@ async def chat(
                     partial(send_event, ChatEvent.STATUS),
                     query_images=uploaded_images,
                     agent=agent,
+                    query_files=attached_file_context,
                     tracer=tracer,
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
@@ -950,6 +992,7 @@ async def chat(
                     custom_filters,
                     query_images=uploaded_images,
                     agent=agent,
+                    query_files=attached_file_context,
                     tracer=tracer,
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
@@ -975,6 +1018,7 @@ async def chat(
                     partial(send_event, ChatEvent.STATUS),
                     query_images=uploaded_images,
                     agent=agent,
+                    query_files=attached_file_context,
                     tracer=tracer,
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
@@ -1015,6 +1059,7 @@ async def chat(
                     partial(send_event, ChatEvent.STATUS),
                     query_images=uploaded_images,
                     agent=agent,
+                    query_files=attached_file_context,
                     tracer=tracer,
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
@@ -1055,6 +1100,7 @@ async def chat(
                 send_status_func=partial(send_event, ChatEvent.STATUS),
                 query_images=uploaded_images,
                 agent=agent,
+                query_files=attached_file_context,
                 tracer=tracer,
             ):
                 if isinstance(result, dict) and ChatEvent.STATUS in result:
@@ -1086,8 +1132,10 @@ async def chat(
                 compiled_references=compiled_references,
                 online_results=online_results,
                 query_images=uploaded_images,
-                tracer=tracer,
                 train_of_thought=train_of_thought,
+                attached_file_context=attached_file_context,
+                raw_query_files=raw_query_files,
+                tracer=tracer,
             )
             content_obj = {
                 "intentType": intent_type,
@@ -1116,6 +1164,7 @@ async def chat(
                 user=user,
                 agent=agent,
                 send_status_func=partial(send_event, ChatEvent.STATUS),
+                query_files=attached_file_context,
                 tracer=tracer,
             ):
                 if isinstance(result, dict) and ChatEvent.STATUS in result:
@@ -1144,8 +1193,10 @@ async def chat(
                 compiled_references=compiled_references,
                 online_results=online_results,
                 query_images=uploaded_images,
-                tracer=tracer,
                 train_of_thought=train_of_thought,
+                attached_file_context=attached_file_context,
+                raw_query_files=raw_query_files,
+                tracer=tracer,
             )
 
             async for result in send_llm_response(json.dumps(content_obj)):
@@ -1171,8 +1222,10 @@ async def chat(
             user_name,
             researched_results,
             uploaded_images,
-            tracer,
             train_of_thought,
+            attached_file_context,
+            raw_query_files,
+            tracer,
         )
 
         # Send Response
diff --git a/src/khoj/routers/api_content.py b/src/khoj/routers/api_content.py
index 72b304ef..40a1fb78 100644
--- a/src/khoj/routers/api_content.py
+++ b/src/khoj/routers/api_content.py
@@ -36,16 +36,18 @@ from khoj.database.models import (
     LocalPlaintextConfig,
     NotionConfig,
 )
+from khoj.processor.content.docx.docx_to_entries import DocxToEntries
+from khoj.processor.content.pdf.pdf_to_entries import PdfToEntries
 from khoj.routers.helpers import (
     ApiIndexedDataLimiter,
     CommonQueryParams,
     configure_content,
+    get_file_content,
     get_user_config,
     update_telemetry_state,
 )
 from khoj.utils import constants, state
 from khoj.utils.config import SearchModels
-from khoj.utils.helpers import get_file_type
 from khoj.utils.rawconfig import (
     ContentConfig,
     FullConfig,
@@ -375,6 +377,75 @@ async def delete_content_source(
     return {"status": "ok"}
 
 
+@api_content.post("/convert", status_code=200)
+@requires(["authenticated"])
+async def convert_documents(
+    request: Request,
+    files: List[UploadFile],
+    client: Optional[str] = None,
+):
+    MAX_FILE_SIZE_MB = 10  # 10MB limit
+    MAX_FILE_SIZE_BYTES = MAX_FILE_SIZE_MB * 1024 * 1024
+
+    converted_files = []
+    supported_files = ["org", "markdown", "pdf", "plaintext", "docx"]
+
+    for file in files:
+        # Check file size first
+        file_size = 0
+        content = await file.read()
+        file_size = len(content)
+        await file.seek(0)  # Reset file pointer
+
+        if file_size > MAX_FILE_SIZE_BYTES:
+            logger.warning(
+                f"Skipped converting oversized file ({file_size / 1024 / 1024:.1f}MB) sent by {client} client: {file.filename}"
+            )
+            continue
+
+        file_data = get_file_content(file)
+        if file_data.file_type in supported_files:
+            extracted_content = (
+                file_data.content.decode(file_data.encoding) if file_data.encoding else file_data.content
+            )
+
+            if file_data.file_type == "docx":
+                entries_per_page = DocxToEntries.extract_text(file_data.content)
+                annotated_pages = [
+                    f"Page {index} of {file_data.name}:\n\n{entry}" for index, entry in enumerate(entries_per_page)
+                ]
+                extracted_content = "\n".join(annotated_pages)
+
+            elif file_data.file_type == "pdf":
+                entries_per_page = PdfToEntries.extract_text(file_data.content)
+                annotated_pages = [
+                    f"Page {index} of {file_data.name}:\n\n{entry}" for index, entry in enumerate(entries_per_page)
+                ]
+                extracted_content = "\n".join(annotated_pages)
+
+            size_in_bytes = len(extracted_content.encode("utf-8"))
+
+            converted_files.append(
+                {
+                    "name": file_data.name,
+                    "content": extracted_content,
+                    "file_type": file_data.file_type,
+                    "size": size_in_bytes,
+                }
+            )
+        else:
+            logger.warning(f"Skipped converting unsupported file type sent by {client} client: {file.filename}")
+
+    update_telemetry_state(
+        request=request,
+        telemetry_type="api",
+        api="convert_documents",
+        client=client,
+    )
+
+    return Response(content=json.dumps(converted_files), media_type="application/json", status_code=200)
+
+
 async def indexer(
     request: Request,
     files: list[UploadFile],
@@ -398,12 +469,13 @@ async def indexer(
     try:
         logger.info(f"📬 Updating content index via API call by {client} client")
         for file in files:
-            file_content = file.file.read()
-            file_type, encoding = get_file_type(file.content_type, file_content)
-            if file_type in index_files:
-                index_files[file_type][file.filename] = file_content.decode(encoding) if encoding else file_content
+            file_data = get_file_content(file)
+            if file_data.file_type in index_files:
+                index_files[file_data.file_type][file_data.name] = (
+                    file_data.content.decode(file_data.encoding) if file_data.encoding else file_data.content
+                )
             else:
-                logger.warning(f"Skipped indexing unsupported file type sent by {client} client: {file.filename}")
+                logger.warning(f"Skipped indexing unsupported file type sent by {client} client: {file_data.name}")
 
         indexer_input = IndexerInput(
             org=index_files["org"],
diff --git a/src/khoj/routers/helpers.py b/src/khoj/routers/helpers.py
index ca78ba35..e645478d 100644
--- a/src/khoj/routers/helpers.py
+++ b/src/khoj/routers/helpers.py
@@ -105,6 +105,7 @@ from khoj.utils.config import OfflineChatProcessorModel
 from khoj.utils.helpers import (
     LRU,
     ConversationCommand,
+    get_file_type,
     is_none_or_empty,
     is_valid_url,
     log_telemetry,
@@ -112,7 +113,7 @@ from khoj.utils.helpers import (
     timer,
     tool_descriptions_for_llm,
 )
-from khoj.utils.rawconfig import LocationData
+from khoj.utils.rawconfig import ChatRequestBody, FileAttachment, FileData, LocationData
 
 logger = logging.getLogger(__name__)
 
@@ -168,6 +169,12 @@ async def is_ready_to_chat(user: KhojUser):
     raise HTTPException(status_code=500, detail="Set your OpenAI API key or enable Local LLM via Khoj settings.")
 
 
+def get_file_content(file: UploadFile):
+    file_content = file.file.read()
+    file_type, encoding = get_file_type(file.content_type, file_content)
+    return FileData(name=file.filename, content=file_content, file_type=file_type, encoding=encoding)
+
+
 def update_telemetry_state(
     request: Request,
     telemetry_type: str,
@@ -249,6 +256,39 @@ async def agenerate_chat_response(*args):
     return await loop.run_in_executor(executor, generate_chat_response, *args)
 
 
+def gather_raw_query_files(
+    query_files: Dict[str, str],
+):
+    """
+    Gather contextual data from the given (raw) files
+    """
+
+    if len(query_files) == 0:
+        return ""
+
+    contextual_data = " ".join(
+        [f"File: {file_name}\n\n{file_content}\n\n" for file_name, file_content in query_files.items()]
+    )
+    return f"I have attached the following files:\n\n{contextual_data}"
+
+
+async def acreate_title_from_history(
+    user: KhojUser,
+    conversation: Conversation,
+):
+    """
+    Create a title from the given conversation history
+    """
+    chat_history = construct_chat_history(conversation.conversation_log)
+
+    title_generation_prompt = prompts.conversation_title_generation.format(chat_history=chat_history)
+
+    with timer("Chat actor: Generate title from conversation history", logger):
+        response = await send_message_to_model_wrapper(title_generation_prompt, user=user)
+
+    return response.strip()
+
+
 async def acreate_title_from_query(query: str, user: KhojUser = None) -> str:
     """
     Create a title from the given query
@@ -294,6 +334,7 @@ async def aget_relevant_information_sources(
     user: KhojUser,
     query_images: List[str] = None,
     agent: Agent = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     """
@@ -331,6 +372,7 @@ async def aget_relevant_information_sources(
             relevant_tools_prompt,
             response_type="json_object",
             user=user,
+            query_files=query_files,
             tracer=tracer,
         )
 
@@ -440,6 +482,7 @@ async def infer_webpage_urls(
     user: KhojUser,
     query_images: List[str] = None,
     agent: Agent = None,
+    query_files: str = None,
     tracer: dict = {},
 ) -> List[str]:
     """
@@ -469,6 +512,7 @@ async def infer_webpage_urls(
             query_images=query_images,
             response_type="json_object",
             user=user,
+            query_files=query_files,
             tracer=tracer,
         )
 
@@ -494,6 +538,7 @@ async def generate_online_subqueries(
     user: KhojUser,
     query_images: List[str] = None,
     agent: Agent = None,
+    query_files: str = None,
     tracer: dict = {},
 ) -> Set[str]:
     """
@@ -523,6 +568,7 @@ async def generate_online_subqueries(
             query_images=query_images,
             response_type="json_object",
             user=user,
+            query_files=query_files,
             tracer=tracer,
         )
 
@@ -645,26 +691,38 @@ async def generate_summary_from_files(
     query_images: List[str] = None,
     agent: Agent = None,
     send_status_func: Optional[Callable] = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     try:
-        file_object = None
+        file_objects = None
         if await EntryAdapters.aagent_has_entries(agent):
             file_names = await EntryAdapters.aget_agent_entry_filepaths(agent)
             if len(file_names) > 0:
-                file_object = await FileObjectAdapters.async_get_file_objects_by_name(None, file_names.pop(), agent)
+                file_objects = await FileObjectAdapters.async_get_file_objects_by_name(None, file_names.pop(), agent)
 
-        if len(file_filters) > 0:
-            file_object = await FileObjectAdapters.async_get_file_objects_by_name(user, file_filters[0])
-
-        if len(file_object) == 0:
-            response_log = "Sorry, I couldn't find the full text of this file."
+        if (file_objects and len(file_objects) == 0 and not query_files) or (not file_objects and not query_files):
+            response_log = "Sorry, I couldn't find anything to summarize."
             yield response_log
             return
-        contextual_data = " ".join([file.raw_text for file in file_object])
+
+        contextual_data = " ".join([f"File: {file.file_name}\n\n{file.raw_text}" for file in file_objects])
+
+        if query_files:
+            contextual_data += f"\n\n{query_files}"
+
         if not q:
             q = "Create a general summary of the file"
-        async for result in send_status_func(f"**Constructing Summary Using:** {file_object[0].file_name}"):
+
+        file_names = [file.file_name for file in file_objects]
+        file_names.extend(file_filters)
+
+        all_file_names = ""
+
+        for file_name in file_names:
+            all_file_names += f"- {file_name}\n"
+
+        async for result in send_status_func(f"**Constructing Summary Using:**\n{all_file_names}"):
             yield {ChatEvent.STATUS: result}
 
         response = await extract_relevant_summary(
@@ -694,6 +752,7 @@ async def generate_excalidraw_diagram(
     user: KhojUser = None,
     agent: Agent = None,
     send_status_func: Optional[Callable] = None,
+    query_files: str = None,
     tracer: dict = {},
 ):
     if send_status_func:
@@ -709,6 +768,7 @@ async def generate_excalidraw_diagram(
         query_images=query_images,
         user=user,
         agent=agent,
+        query_files=query_files,
         tracer=tracer,
     )
 
@@ -735,6 +795,7 @@ async def generate_better_diagram_description(
     query_images: List[str] = None,
     user: KhojUser = None,
     agent: Agent = None,
+    query_files: str = None,
     tracer: dict = {},
 ) -> str:
     """
@@ -773,7 +834,11 @@ async def generate_better_diagram_description(
 
     with timer("Chat actor: Generate better diagram description", logger):
         response = await send_message_to_model_wrapper(
-            improve_diagram_description_prompt, query_images=query_images, user=user, tracer=tracer
+            improve_diagram_description_prompt,
+            query_images=query_images,
+            user=user,
+            query_files=query_files,
+            tracer=tracer,
         )
         response = response.strip()
         if response.startswith(('"', "'")) and response.endswith(('"', "'")):
@@ -820,6 +885,7 @@ async def generate_better_image_prompt(
     query_images: Optional[List[str]] = None,
     user: KhojUser = None,
     agent: Agent = None,
+    query_files: str = "",
     tracer: dict = {},
 ) -> str:
     """
@@ -868,7 +934,7 @@ async def generate_better_image_prompt(
 
     with timer("Chat actor: Generate contextual image prompt", logger):
         response = await send_message_to_model_wrapper(
-            image_prompt, query_images=query_images, user=user, tracer=tracer
+            image_prompt, query_images=query_images, user=user, query_files=query_files, tracer=tracer
         )
         response = response.strip()
         if response.startswith(('"', "'")) and response.endswith(('"', "'")):
@@ -884,6 +950,7 @@ async def send_message_to_model_wrapper(
     user: KhojUser = None,
     query_images: List[str] = None,
     context: str = "",
+    query_files: str = None,
     tracer: dict = {},
 ):
     conversation_config: ChatModelOptions = await ConversationAdapters.aget_default_conversation_config(user)
@@ -923,6 +990,7 @@ async def send_message_to_model_wrapper(
             max_prompt_size=max_tokens,
             vision_enabled=vision_available,
             model_type=conversation_config.model_type,
+            query_files=query_files,
         )
 
         return send_message_to_model_offline(
@@ -949,6 +1017,7 @@ async def send_message_to_model_wrapper(
             vision_enabled=vision_available,
             query_images=query_images,
             model_type=conversation_config.model_type,
+            query_files=query_files,
         )
 
         return send_message_to_model(
@@ -971,6 +1040,7 @@ async def send_message_to_model_wrapper(
             vision_enabled=vision_available,
             query_images=query_images,
             model_type=conversation_config.model_type,
+            query_files=query_files,
         )
 
         return anthropic_send_message_to_model(
@@ -992,6 +1062,7 @@ async def send_message_to_model_wrapper(
             vision_enabled=vision_available,
             query_images=query_images,
             model_type=conversation_config.model_type,
+            query_files=query_files,
         )
 
         return gemini_send_message_to_model(
@@ -1006,6 +1077,7 @@ def send_message_to_model_wrapper_sync(
     system_message: str = "",
     response_type: str = "text",
     user: KhojUser = None,
+    query_files: str = "",
     tracer: dict = {},
 ):
     conversation_config: ChatModelOptions = ConversationAdapters.get_default_conversation_config(user)
@@ -1030,6 +1102,7 @@ def send_message_to_model_wrapper_sync(
             max_prompt_size=max_tokens,
             vision_enabled=vision_available,
             model_type=conversation_config.model_type,
+            query_files=query_files,
         )
 
         return send_message_to_model_offline(
@@ -1051,6 +1124,7 @@ def send_message_to_model_wrapper_sync(
             max_prompt_size=max_tokens,
             vision_enabled=vision_available,
             model_type=conversation_config.model_type,
+            query_files=query_files,
         )
 
         openai_response = send_message_to_model(
@@ -1072,6 +1146,7 @@ def send_message_to_model_wrapper_sync(
             max_prompt_size=max_tokens,
             vision_enabled=vision_available,
             model_type=conversation_config.model_type,
+            query_files=query_files,
         )
 
         return anthropic_send_message_to_model(
@@ -1091,6 +1166,7 @@ def send_message_to_model_wrapper_sync(
             max_prompt_size=max_tokens,
             vision_enabled=vision_available,
             model_type=conversation_config.model_type,
+            query_files=query_files,
         )
 
         return gemini_send_message_to_model(
@@ -1120,8 +1196,10 @@ def generate_chat_response(
     user_name: Optional[str] = None,
     meta_research: str = "",
     query_images: Optional[List[str]] = None,
-    tracer: dict = {},
     train_of_thought: List[Any] = [],
+    query_files: str = None,
+    raw_query_files: List[FileAttachment] = None,
+    tracer: dict = {},
 ) -> Tuple[Union[ThreadedGenerator, Iterator[str]], Dict[str, str]]:
     # Initialize Variables
     chat_response = None
@@ -1142,8 +1220,9 @@ def generate_chat_response(
             client_application=client_application,
             conversation_id=conversation_id,
             query_images=query_images,
-            tracer=tracer,
             train_of_thought=train_of_thought,
+            raw_query_files=raw_query_files,
+            tracer=tracer,
         )
 
         query_to_run = q
@@ -1177,6 +1256,7 @@ def generate_chat_response(
                 location_data=location_data,
                 user_name=user_name,
                 agent=agent,
+                query_files=query_files,
                 tracer=tracer,
             )
 
@@ -1202,6 +1282,7 @@ def generate_chat_response(
                 user_name=user_name,
                 agent=agent,
                 vision_available=vision_available,
+                query_files=query_files,
                 tracer=tracer,
             )
 
@@ -1224,6 +1305,7 @@ def generate_chat_response(
                 user_name=user_name,
                 agent=agent,
                 vision_available=vision_available,
+                query_files=query_files,
                 tracer=tracer,
             )
         elif conversation_config.model_type == ChatModelOptions.ModelType.GOOGLE:
@@ -1243,7 +1325,9 @@ def generate_chat_response(
                 location_data=location_data,
                 user_name=user_name,
                 agent=agent,
+                query_images=query_images,
                 vision_available=vision_available,
+                query_files=query_files,
                 tracer=tracer,
             )
 
@@ -1256,23 +1340,6 @@ def generate_chat_response(
     return chat_response, metadata
 
 
-class ChatRequestBody(BaseModel):
-    q: str
-    n: Optional[int] = 7
-    d: Optional[float] = None
-    stream: Optional[bool] = False
-    title: Optional[str] = None
-    conversation_id: Optional[str] = None
-    turn_id: Optional[str] = None
-    city: Optional[str] = None
-    region: Optional[str] = None
-    country: Optional[str] = None
-    country_code: Optional[str] = None
-    timezone: Optional[str] = None
-    images: Optional[list[str]] = None
-    create_new: Optional[bool] = False
-
-
 class DeleteMessageRequestBody(BaseModel):
     conversation_id: str
     turn_id: str
diff --git a/src/khoj/routers/research.py b/src/khoj/routers/research.py
index 1caf7c96..abf8f96c 100644
--- a/src/khoj/routers/research.py
+++ b/src/khoj/routers/research.py
@@ -11,6 +11,7 @@ from khoj.processor.conversation import prompts
 from khoj.processor.conversation.utils import (
     InformationCollectionIteration,
     clean_json,
+    construct_chat_history,
     construct_iteration_history,
     construct_tool_chat_history,
 )
@@ -19,8 +20,6 @@ from khoj.processor.tools.run_code import run_code
 from khoj.routers.api import extract_references_and_questions
 from khoj.routers.helpers import (
     ChatEvent,
-    construct_chat_history,
-    extract_relevant_info,
     generate_summary_from_files,
     send_message_to_model_wrapper,
 )
@@ -47,6 +46,7 @@ async def apick_next_tool(
     max_iterations: int = 5,
     send_status_func: Optional[Callable] = None,
     tracer: dict = {},
+    query_files: str = None,
 ):
     """Given a query, determine which of the available tools the agent should use in order to answer appropriately."""
 
@@ -92,6 +92,7 @@ async def apick_next_tool(
                 response_type="json_object",
                 user=user,
                 query_images=query_images,
+                query_files=query_files,
                 tracer=tracer,
             )
     except Exception as e:
@@ -151,6 +152,7 @@ async def execute_information_collection(
     location: LocationData = None,
     file_filters: List[str] = [],
     tracer: dict = {},
+    query_files: str = None,
 ):
     current_iteration = 0
     MAX_ITERATIONS = 5
@@ -174,6 +176,7 @@ async def execute_information_collection(
             MAX_ITERATIONS,
             send_status_func,
             tracer=tracer,
+            query_files=query_files,
         ):
             if isinstance(result, dict) and ChatEvent.STATUS in result:
                 yield result[ChatEvent.STATUS]
@@ -204,6 +207,7 @@ async def execute_information_collection(
                 previous_inferred_queries=previous_inferred_queries,
                 agent=agent,
                 tracer=tracer,
+                query_files=query_files,
             ):
                 if isinstance(result, dict) and ChatEvent.STATUS in result:
                     yield result[ChatEvent.STATUS]
@@ -265,6 +269,7 @@ async def execute_information_collection(
                     query_images=query_images,
                     agent=agent,
                     tracer=tracer,
+                    query_files=query_files,
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
                         yield result[ChatEvent.STATUS]
@@ -295,6 +300,7 @@ async def execute_information_collection(
                     send_status_func,
                     query_images=query_images,
                     agent=agent,
+                    query_files=query_files,
                     tracer=tracer,
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
@@ -320,6 +326,7 @@ async def execute_information_collection(
                     query_images=query_images,
                     agent=agent,
                     send_status_func=send_status_func,
+                    query_files=query_files,
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
                         yield result[ChatEvent.STATUS]
diff --git a/src/khoj/utils/rawconfig.py b/src/khoj/utils/rawconfig.py
index 15f5ea01..9a7a75a8 100644
--- a/src/khoj/utils/rawconfig.py
+++ b/src/khoj/utils/rawconfig.py
@@ -138,6 +138,38 @@ class SearchResponse(ConfigBase):
     corpus_id: str
 
 
+class FileData(BaseModel):
+    name: str
+    content: bytes
+    file_type: str
+    encoding: str | None = None
+
+
+class FileAttachment(BaseModel):
+    name: str
+    content: str
+    file_type: str
+    size: int
+
+
+class ChatRequestBody(BaseModel):
+    q: str
+    n: Optional[int] = 7
+    d: Optional[float] = None
+    stream: Optional[bool] = False
+    title: Optional[str] = None
+    conversation_id: Optional[str] = None
+    turn_id: Optional[str] = None
+    city: Optional[str] = None
+    region: Optional[str] = None
+    country: Optional[str] = None
+    country_code: Optional[str] = None
+    timezone: Optional[str] = None
+    images: Optional[list[str]] = None
+    files: Optional[list[FileAttachment]] = []
+    create_new: Optional[bool] = False
+
+
 class Entry:
     raw: str
     compiled: str
diff --git a/tests/test_offline_chat_director.py b/tests/test_offline_chat_director.py
index afb5d4ce..45f540ed 100644
--- a/tests/test_offline_chat_director.py
+++ b/tests/test_offline_chat_director.py
@@ -337,7 +337,6 @@ def test_summarize_one_file(client_offline_chat, default_user2: KhojUser):
     # Assert
     assert response_message != ""
     assert response_message != "No files selected for summarization. Please add files using the section on the left."
-    assert response_message != "Only one file can be selected for summarization."
 
 
 @pytest.mark.django_db(transaction=True)
@@ -375,7 +374,6 @@ def test_summarize_extra_text(client_offline_chat, default_user2: KhojUser):
     # Assert
     assert response_message != ""
     assert response_message != "No files selected for summarization. Please add files using the section on the left."
-    assert response_message != "Only one file can be selected for summarization."
 
 
 @pytest.mark.django_db(transaction=True)
@@ -404,7 +402,7 @@ def test_summarize_multiple_files(client_offline_chat, default_user2: KhojUser):
     response_message = response.json()["response"]
 
     # Assert
-    assert response_message == "Only one file can be selected for summarization."
+    assert response_message is not None
 
 
 @pytest.mark.django_db(transaction=True)
@@ -460,7 +458,6 @@ def test_summarize_different_conversation(client_offline_chat, default_user2: Kh
     # Assert
     assert response_message != ""
     assert response_message != "No files selected for summarization. Please add files using the section on the left."
-    assert response_message != "Only one file can be selected for summarization."
 
 
 @pytest.mark.django_db(transaction=True)
diff --git a/tests/test_openai_chat_director.py b/tests/test_openai_chat_director.py
index 7d460408..56dde6d3 100644
--- a/tests/test_openai_chat_director.py
+++ b/tests/test_openai_chat_director.py
@@ -312,7 +312,6 @@ def test_summarize_one_file(chat_client, default_user2: KhojUser):
     # Assert
     assert response_message != ""
     assert response_message != "No files selected for summarization. Please add files using the section on the left."
-    assert response_message != "Only one file can be selected for summarization."
 
 
 @pytest.mark.django_db(transaction=True)
@@ -344,7 +343,6 @@ def test_summarize_extra_text(chat_client, default_user2: KhojUser):
     # Assert
     assert response_message != ""
     assert response_message != "No files selected for summarization. Please add files using the section on the left."
-    assert response_message != "Only one file can be selected for summarization."
 
 
 @pytest.mark.django_db(transaction=True)
@@ -371,7 +369,7 @@ def test_summarize_multiple_files(chat_client, default_user2: KhojUser):
     response_message = response.json()["response"]
 
     # Assert
-    assert response_message == "Only one file can be selected for summarization."
+    assert response_message is not None
 
 
 @pytest.mark.django_db(transaction=True)
@@ -435,7 +433,6 @@ def test_summarize_different_conversation(chat_client, default_user2: KhojUser):
     assert (
         response_message_conv1 != "No files selected for summarization. Please add files using the section on the left."
     )
-    assert response_message_conv1 != "Only one file can be selected for summarization."
 
 
 @pytest.mark.django_db(transaction=True)