diff --git a/src/khoj/configure.py b/src/khoj/configure.py
index 84b87ff3..bba03dc2 100644
--- a/src/khoj/configure.py
+++ b/src/khoj/configure.py
@@ -37,45 +37,63 @@ from khoj.search_filter.file_filter import FileFilter
 logger = logging.getLogger(__name__)
 
 
-def configure_server(args, required=False):
-    if args.config is None:
-        if required:
-            logger.error(
-                f"Exiting as Khoj is not configured.\nConfigure it via http://localhost:42110/config or by editing {state.config_file}."
-            )
-            sys.exit(1)
-        else:
-            logger.warning(
-                f"Khoj is not configured.\nConfigure it via http://localhost:42110/config, plugins or by editing {state.config_file}."
-            )
-            return
-    else:
-        state.config = args.config
+def initialize_server(
+    config: Optional[FullConfig], regenerate: bool, type: Optional[SearchType] = None, required=False
+):
+    if config is None and required:
+        logger.error(
+            f"🚨 Exiting as Khoj is not configured.\nConfigure it via http://localhost:42110/config or by editing {state.config_file}."
+        )
+        sys.exit(1)
+    elif config is None:
+        logger.warning(
+            f"🚨 Khoj is not configured.\nConfigure it via http://localhost:42110/config, plugins or by editing {state.config_file}."
+        )
+        return None
+
+    try:
+        configure_server(config, regenerate, type)
+    except Exception as e:
+        logger.error(f"🚨 Failed to configure server on app load: {e}", exc_info=True)
+
+
+def configure_server(config: FullConfig, regenerate: bool, search_type: Optional[SearchType] = None):
+    # Update Config
+    state.config = config
 
     # Initialize Processor from Config
-    state.processor_config = configure_processor(args.config.processor)
+    try:
+        state.config_lock.acquire()
+        state.processor_config = configure_processor(state.config.processor)
+    except Exception as e:
+        logger.error(f"🚨 Failed to configure processor")
+        raise e
+    finally:
+        state.config_lock.release()
 
     # Initialize Search Models from Config
     try:
-        state.search_index_lock.acquire()
+        state.config_lock.acquire()
         state.SearchType = configure_search_types(state.config)
         state.search_models = configure_search(state.search_models, state.config.search_type)
     except Exception as e:
-        logger.error(f"🚨 Error configuring search models on app load: {e}")
+        logger.error(f"🚨 Failed to configure search models")
+        raise e
     finally:
-        state.search_index_lock.release()
+        state.config_lock.release()
 
     # Initialize Content from Config
     if state.search_models:
         try:
-            state.search_index_lock.acquire()
+            state.config_lock.acquire()
             state.content_index = configure_content(
-                state.content_index, state.config.content_type, state.search_models, args.regenerate
+                state.content_index, state.config.content_type, state.search_models, regenerate, search_type
             )
         except Exception as e:
-            logger.error(f"🚨 Error configuring content index on app load: {e}")
+            logger.error(f"🚨 Failed to index content")
+            raise e
         finally:
-            state.search_index_lock.release()
+            state.config_lock.release()
 
 
 def configure_routes(app):
@@ -95,7 +113,7 @@ if not state.demo:
     @schedule.repeat(schedule.every(61).minutes)
     def update_search_index():
         try:
-            state.search_index_lock.acquire()
+            state.config_lock.acquire()
             state.content_index = configure_content(
                 state.content_index, state.config.content_type, state.search_models, regenerate=False
             )
@@ -103,7 +121,7 @@ if not state.demo:
         except Exception as e:
             logger.error(f"🚨 Error updating content index via Scheduler: {e}")
         finally:
-            state.search_index_lock.release()
+            state.config_lock.release()
 
 
 def configure_search_types(config: FullConfig):
@@ -118,10 +136,10 @@ def configure_search_types(config: FullConfig):
     return Enum("SearchType", merge_dicts(core_search_types, plugin_search_types))
 
 
-def configure_search(search_models: SearchModels, search_config: SearchConfig) -> Optional[SearchModels]:
+def configure_search(search_models: SearchModels, search_config: Optional[SearchConfig]) -> Optional[SearchModels]:
     # Run Validation Checks
     if search_config is None:
-        logger.warning("🚨 No Search type is configured.")
+        logger.warning("🚨 No Search configuration available.")
         return None
     if search_models is None:
         search_models = SearchModels()
@@ -147,7 +165,7 @@ def configure_content(
 ) -> Optional[ContentIndex]:
     # Run Validation Checks
     if content_config is None:
-        logger.warning("🚨 No Content type is configured.")
+        logger.warning("🚨 No Content configuration available.")
         return None
     if content_index is None:
         content_index = ContentIndex()
@@ -242,9 +260,10 @@ def configure_content(
     return content_index
 
 
-def configure_processor(processor_config: ProcessorConfig):
+def configure_processor(processor_config: Optional[ProcessorConfig]):
     if not processor_config:
-        return
+        logger.warning("🚨 No Processor configuration available.")
+        return None
 
     processor = ProcessorConfigModel()
 
diff --git a/src/khoj/main.py b/src/khoj/main.py
index 9f7fe8df..6689805c 100644
--- a/src/khoj/main.py
+++ b/src/khoj/main.py
@@ -25,7 +25,7 @@ from rich.logging import RichHandler
 import schedule
 
 # Internal Packages
-from khoj.configure import configure_routes, configure_server
+from khoj.configure import configure_routes, initialize_server
 from khoj.utils import state
 from khoj.utils.cli import cli
 
@@ -70,7 +70,7 @@ def run():
         poll_task_scheduler()
 
         # Start Server
-        configure_server(args, required=False)
+        initialize_server(args.config, args.regenerate, required=False)
         configure_routes(app)
         start_server(app, host=args.host, port=args.port, socket=args.socket)
     else:
@@ -93,7 +93,7 @@ def run():
             tray.show()
 
         # Setup Server
-        configure_server(args, required=False)
+        initialize_server(args.config, args.regenerate, required=False)
         configure_routes(app)
         server = ServerThread(start_server_func=lambda: start_server(app, host=args.host, port=args.port))
 
diff --git a/src/khoj/processor/github/github_to_jsonl.py b/src/khoj/processor/github/github_to_jsonl.py
index dd797c31..91dbd6da 100644
--- a/src/khoj/processor/github/github_to_jsonl.py
+++ b/src/khoj/processor/github/github_to_jsonl.py
@@ -13,9 +13,8 @@ from khoj.utils.rawconfig import Entry, GithubContentConfig, GithubRepoConfig
 from khoj.processor.markdown.markdown_to_jsonl import MarkdownToJsonl
 from khoj.processor.org_mode.org_to_jsonl import OrgToJsonl
 from khoj.processor.text_to_jsonl import TextToJsonl
-from khoj.utils.jsonl import dump_jsonl, compress_jsonl_data
+from khoj.utils.jsonl import compress_jsonl_data
 from khoj.utils.rawconfig import Entry
-from khoj.utils import state
 
 
 logger = logging.getLogger(__name__)
@@ -38,7 +37,7 @@ class GithubToJsonl(TextToJsonl):
         else:
             return
 
-    def process(self, previous_entries=None):
+    def process(self, previous_entries=[]):
         current_entries = []
         for repo in self.config.repos:
             current_entries += self.process_repo(repo)
@@ -98,10 +97,7 @@ class GithubToJsonl(TextToJsonl):
             jsonl_data = MarkdownToJsonl.convert_markdown_maps_to_jsonl(entries)
 
             # Compress JSONL formatted Data
-            if self.config.compressed_jsonl.suffix == ".gz":
-                compress_jsonl_data(jsonl_data, self.config.compressed_jsonl)
-            elif self.config.compressed_jsonl.suffix == ".jsonl":
-                dump_jsonl(jsonl_data, self.config.compressed_jsonl)
+            compress_jsonl_data(jsonl_data, self.config.compressed_jsonl)
 
         return entries_with_ids
 
diff --git a/src/khoj/processor/jsonl/jsonl_to_jsonl.py b/src/khoj/processor/jsonl/jsonl_to_jsonl.py
index f743d5d5..3c824545 100644
--- a/src/khoj/processor/jsonl/jsonl_to_jsonl.py
+++ b/src/khoj/processor/jsonl/jsonl_to_jsonl.py
@@ -7,7 +7,7 @@ from typing import List
 # Internal Packages
 from khoj.processor.text_to_jsonl import TextToJsonl
 from khoj.utils.helpers import get_absolute_path, timer
-from khoj.utils.jsonl import load_jsonl, dump_jsonl, compress_jsonl_data
+from khoj.utils.jsonl import load_jsonl, compress_jsonl_data
 from khoj.utils.rawconfig import Entry
 
 
@@ -16,7 +16,7 @@ logger = logging.getLogger(__name__)
 
 class JsonlToJsonl(TextToJsonl):
     # Define Functions
-    def process(self, previous_entries=None):
+    def process(self, previous_entries=[]):
         # Extract required fields from config
         input_jsonl_files, input_jsonl_filter, output_file = (
             self.config.input_files,
@@ -38,15 +38,9 @@ class JsonlToJsonl(TextToJsonl):
 
         # Identify, mark and merge any new entries with previous entries
         with timer("Identify new or updated entries", logger):
-            if not previous_entries:
-                entries_with_ids = list(enumerate(current_entries))
-            else:
-                entries_with_ids = TextToJsonl.mark_entries_for_update(
-                    current_entries,
-                    previous_entries,
-                    key="compiled",
-                    logger=logger,
-                )
+            entries_with_ids = TextToJsonl.mark_entries_for_update(
+                current_entries, previous_entries, key="compiled", logger=logger
+            )
 
         with timer("Write entries to JSONL file", logger):
             # Process Each Entry from All Notes Files
@@ -54,10 +48,7 @@ class JsonlToJsonl(TextToJsonl):
             jsonl_data = JsonlToJsonl.convert_entries_to_jsonl(entries)
 
             # Compress JSONL formatted Data
-            if output_file.suffix == ".gz":
-                compress_jsonl_data(jsonl_data, output_file)
-            elif output_file.suffix == ".jsonl":
-                dump_jsonl(jsonl_data, output_file)
+            compress_jsonl_data(jsonl_data, output_file)
 
         return entries_with_ids
 
diff --git a/src/khoj/processor/markdown/markdown_to_jsonl.py b/src/khoj/processor/markdown/markdown_to_jsonl.py
index 21cbda72..b6acbfbb 100644
--- a/src/khoj/processor/markdown/markdown_to_jsonl.py
+++ b/src/khoj/processor/markdown/markdown_to_jsonl.py
@@ -10,7 +10,7 @@ from typing import List
 from khoj.processor.text_to_jsonl import TextToJsonl
 from khoj.utils.helpers import get_absolute_path, is_none_or_empty, timer
 from khoj.utils.constants import empty_escape_sequences
-from khoj.utils.jsonl import dump_jsonl, compress_jsonl_data
+from khoj.utils.jsonl import compress_jsonl_data
 from khoj.utils.rawconfig import Entry, TextContentConfig
 
 
@@ -23,7 +23,7 @@ class MarkdownToJsonl(TextToJsonl):
         self.config = config
 
     # Define Functions
-    def process(self, previous_entries=None):
+    def process(self, previous_entries=[]):
         # Extract required fields from config
         markdown_files, markdown_file_filter, output_file = (
             self.config.input_files,
@@ -51,12 +51,9 @@ class MarkdownToJsonl(TextToJsonl):
 
         # Identify, mark and merge any new entries with previous entries
         with timer("Identify new or updated entries", logger):
-            if not previous_entries:
-                entries_with_ids = list(enumerate(current_entries))
-            else:
-                entries_with_ids = TextToJsonl.mark_entries_for_update(
-                    current_entries, previous_entries, key="compiled", logger=logger
-                )
+            entries_with_ids = TextToJsonl.mark_entries_for_update(
+                current_entries, previous_entries, key="compiled", logger=logger
+            )
 
         with timer("Write markdown entries to JSONL file", logger):
             # Process Each Entry from All Notes Files
@@ -64,10 +61,7 @@ class MarkdownToJsonl(TextToJsonl):
             jsonl_data = MarkdownToJsonl.convert_markdown_maps_to_jsonl(entries)
 
             # Compress JSONL formatted Data
-            if output_file.suffix == ".gz":
-                compress_jsonl_data(jsonl_data, output_file)
-            elif output_file.suffix == ".jsonl":
-                dump_jsonl(jsonl_data, output_file)
+            compress_jsonl_data(jsonl_data, output_file)
 
         return entries_with_ids
 
diff --git a/src/khoj/processor/notion/notion_to_jsonl.py b/src/khoj/processor/notion/notion_to_jsonl.py
index 20a11cd7..489f0341 100644
--- a/src/khoj/processor/notion/notion_to_jsonl.py
+++ b/src/khoj/processor/notion/notion_to_jsonl.py
@@ -8,7 +8,7 @@ import requests
 from khoj.utils.helpers import timer
 from khoj.utils.rawconfig import Entry, NotionContentConfig
 from khoj.processor.text_to_jsonl import TextToJsonl
-from khoj.utils.jsonl import dump_jsonl, compress_jsonl_data
+from khoj.utils.jsonl import compress_jsonl_data
 from khoj.utils.rawconfig import Entry
 
 from enum import Enum
@@ -80,7 +80,7 @@ class NotionToJsonl(TextToJsonl):
 
         self.body_params = {"page_size": 100}
 
-    def process(self, previous_entries=None):
+    def process(self, previous_entries=[]):
         current_entries = []
 
         # Get all pages
@@ -240,12 +240,9 @@ class NotionToJsonl(TextToJsonl):
     def update_entries_with_ids(self, current_entries, previous_entries):
         # Identify, mark and merge any new entries with previous entries
         with timer("Identify new or updated entries", logger):
-            if not previous_entries:
-                entries_with_ids = list(enumerate(current_entries))
-            else:
-                entries_with_ids = TextToJsonl.mark_entries_for_update(
-                    current_entries, previous_entries, key="compiled", logger=logger
-                )
+            entries_with_ids = TextToJsonl.mark_entries_for_update(
+                current_entries, previous_entries, key="compiled", logger=logger
+            )
 
         with timer("Write Notion entries to JSONL file", logger):
             # Process Each Entry from all Notion entries
@@ -253,9 +250,6 @@ class NotionToJsonl(TextToJsonl):
             jsonl_data = TextToJsonl.convert_text_maps_to_jsonl(entries)
 
             # Compress JSONL formatted Data
-            if self.config.compressed_jsonl.suffix == ".gz":
-                compress_jsonl_data(jsonl_data, self.config.compressed_jsonl)
-            elif self.config.compressed_jsonl.suffix == ".jsonl":
-                dump_jsonl(jsonl_data, self.config.compressed_jsonl)
+            compress_jsonl_data(jsonl_data, self.config.compressed_jsonl)
 
         return entries_with_ids
diff --git a/src/khoj/processor/org_mode/org_to_jsonl.py b/src/khoj/processor/org_mode/org_to_jsonl.py
index 664427d9..b3bc06fd 100644
--- a/src/khoj/processor/org_mode/org_to_jsonl.py
+++ b/src/khoj/processor/org_mode/org_to_jsonl.py
@@ -8,7 +8,7 @@ from typing import Iterable, List
 from khoj.processor.org_mode import orgnode
 from khoj.processor.text_to_jsonl import TextToJsonl
 from khoj.utils.helpers import get_absolute_path, is_none_or_empty, timer
-from khoj.utils.jsonl import dump_jsonl, compress_jsonl_data
+from khoj.utils.jsonl import compress_jsonl_data
 from khoj.utils.rawconfig import Entry, TextContentConfig
 from khoj.utils import state
 
@@ -22,7 +22,7 @@ class OrgToJsonl(TextToJsonl):
         self.config = config
 
     # Define Functions
-    def process(self, previous_entries: List[Entry] = None):
+    def process(self, previous_entries: List[Entry] = []):
         # Extract required fields from config
         org_files, org_file_filter, output_file = (
             self.config.input_files,
@@ -51,9 +51,7 @@ class OrgToJsonl(TextToJsonl):
             current_entries = self.split_entries_by_max_tokens(current_entries, max_tokens=256)
 
         # Identify, mark and merge any new entries with previous entries
-        if not previous_entries:
-            entries_with_ids = list(enumerate(current_entries))
-        else:
+        with timer("Identify new or updated entries", logger):
             entries_with_ids = TextToJsonl.mark_entries_for_update(
                 current_entries, previous_entries, key="compiled", logger=logger
             )
@@ -64,10 +62,7 @@ class OrgToJsonl(TextToJsonl):
             jsonl_data = self.convert_org_entries_to_jsonl(entries)
 
             # Compress JSONL formatted Data
-            if output_file.suffix == ".gz":
-                compress_jsonl_data(jsonl_data, output_file)
-            elif output_file.suffix == ".jsonl":
-                dump_jsonl(jsonl_data, output_file)
+            compress_jsonl_data(jsonl_data, output_file)
 
         return entries_with_ids
 
@@ -125,9 +120,13 @@ class OrgToJsonl(TextToJsonl):
                 # Ignore title notes i.e notes with just headings and empty body
                 continue
 
+            todo_str = f"{parsed_entry.todo} " if parsed_entry.todo else ""
             # Prepend filename as top heading to entry
             filename = Path(entry_to_file_map[parsed_entry]).stem
-            heading = f"* {filename}\n** {parsed_entry.heading}." if parsed_entry.heading else f"* {filename}."
+            if parsed_entry.heading:
+                heading = f"* {filename}\n** {todo_str}{parsed_entry.heading}."
+            else:
+                heading = f"* {filename}."
 
             compiled = heading
             if state.verbose > 2:
diff --git a/src/khoj/processor/pdf/pdf_to_jsonl.py b/src/khoj/processor/pdf/pdf_to_jsonl.py
index c5c395bc..f8a20692 100644
--- a/src/khoj/processor/pdf/pdf_to_jsonl.py
+++ b/src/khoj/processor/pdf/pdf_to_jsonl.py
@@ -10,7 +10,7 @@ from langchain.document_loaders import PyPDFLoader
 # Internal Packages
 from khoj.processor.text_to_jsonl import TextToJsonl
 from khoj.utils.helpers import get_absolute_path, is_none_or_empty, timer
-from khoj.utils.jsonl import dump_jsonl, compress_jsonl_data
+from khoj.utils.jsonl import compress_jsonl_data
 from khoj.utils.rawconfig import Entry
 
 
@@ -19,7 +19,7 @@ logger = logging.getLogger(__name__)
 
 class PdfToJsonl(TextToJsonl):
     # Define Functions
-    def process(self, previous_entries=None):
+    def process(self, previous_entries=[]):
         # Extract required fields from config
         pdf_files, pdf_file_filter, output_file = (
             self.config.input_files,
@@ -45,12 +45,9 @@ class PdfToJsonl(TextToJsonl):
 
         # Identify, mark and merge any new entries with previous entries
         with timer("Identify new or updated entries", logger):
-            if not previous_entries:
-                entries_with_ids = list(enumerate(current_entries))
-            else:
-                entries_with_ids = TextToJsonl.mark_entries_for_update(
-                    current_entries, previous_entries, key="compiled", logger=logger
-                )
+            entries_with_ids = TextToJsonl.mark_entries_for_update(
+                current_entries, previous_entries, key="compiled", logger=logger
+            )
 
         with timer("Write PDF entries to JSONL file", logger):
             # Process Each Entry from All Notes Files
@@ -58,10 +55,7 @@ class PdfToJsonl(TextToJsonl):
             jsonl_data = PdfToJsonl.convert_pdf_maps_to_jsonl(entries)
 
             # Compress JSONL formatted Data
-            if output_file.suffix == ".gz":
-                compress_jsonl_data(jsonl_data, output_file)
-            elif output_file.suffix == ".jsonl":
-                dump_jsonl(jsonl_data, output_file)
+            compress_jsonl_data(jsonl_data, output_file)
 
         return entries_with_ids
 
diff --git a/src/khoj/processor/text_to_jsonl.py b/src/khoj/processor/text_to_jsonl.py
index a4d01cf5..f92ab7b1 100644
--- a/src/khoj/processor/text_to_jsonl.py
+++ b/src/khoj/processor/text_to_jsonl.py
@@ -17,7 +17,7 @@ class TextToJsonl(ABC):
         self.config = config
 
     @abstractmethod
-    def process(self, previous_entries: List[Entry] = None) -> List[Tuple[int, Entry]]:
+    def process(self, previous_entries: List[Entry] = []) -> List[Tuple[int, Entry]]:
         ...
 
     @staticmethod
@@ -78,16 +78,23 @@ class TextToJsonl(ABC):
             # All entries that exist in both current and previous sets are kept
             existing_entry_hashes = set(current_entry_hashes) & set(previous_entry_hashes)
 
+            # load new entries in the order in which they are processed for a stable sort
+            new_entries = [
+                (current_entry_hashes.index(entry_hash), hash_to_current_entries[entry_hash])
+                for entry_hash in new_entry_hashes
+            ]
+            new_entries_sorted = sorted(new_entries, key=lambda e: e[0])
             # Mark new entries with -1 id to flag for later embeddings generation
-            new_entries = [(-1, hash_to_current_entries[entry_hash]) for entry_hash in new_entry_hashes]
+            new_entries_sorted = [(-1, entry[1]) for entry in new_entries_sorted]
+
             # Set id of existing entries to their previous ids to reuse their existing encoded embeddings
             existing_entries = [
                 (previous_entry_hashes.index(entry_hash), hash_to_previous_entries[entry_hash])
                 for entry_hash in existing_entry_hashes
             ]
-
             existing_entries_sorted = sorted(existing_entries, key=lambda e: e[0])
-            entries_with_ids = existing_entries_sorted + new_entries
+
+            entries_with_ids = existing_entries_sorted + new_entries_sorted
 
         return entries_with_ids
 
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index 50e8e1f2..834e8997 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -5,20 +5,20 @@ import time
 import yaml
 import logging
 import json
-from typing import List, Optional, Union
+from typing import Iterable, List, Optional, Union
 
 # External Packages
 from fastapi import APIRouter, HTTPException, Header, Request
 from sentence_transformers import util
 
 # Internal Packages
-from khoj.configure import configure_content, configure_processor, configure_search
+from khoj.configure import configure_processor, configure_server
 from khoj.search_type import image_search, text_search
 from khoj.search_filter.date_filter import DateFilter
 from khoj.search_filter.file_filter import FileFilter
 from khoj.search_filter.word_filter import WordFilter
 from khoj.utils.config import TextSearchModel
-from khoj.utils.helpers import log_telemetry, timer
+from khoj.utils.helpers import timer
 from khoj.utils.rawconfig import (
     ContentConfig,
     FullConfig,
@@ -524,34 +524,26 @@ def update(
     referer: Optional[str] = Header(None),
     host: Optional[str] = Header(None),
 ):
+    if not state.config:
+        error_msg = f"🚨 Khoj is not configured.\nConfigure it via http://localhost:42110/config, plugins or by editing {state.config_file}."
+        logger.warning(error_msg)
+        raise HTTPException(status_code=500, detail=error_msg)
     try:
-        state.search_index_lock.acquire()
-        try:
-            if state.config and state.config.search_type:
-                state.search_models = configure_search(state.search_models, state.config.search_type)
-            if state.search_models:
-                state.content_index = configure_content(
-                    state.content_index, state.config.content_type, state.search_models, regenerate=force or False, t=t
-                )
-        except Exception as e:
-            logger.error(e)
-            raise HTTPException(status_code=500, detail=str(e))
-        finally:
-            state.search_index_lock.release()
-    except ValueError as e:
-        logger.error(e)
-        raise HTTPException(status_code=500, detail=str(e))
+        configure_server(state.config, regenerate=force or False, search_type=t)
+    except Exception as e:
+        error_msg = f"🚨 Failed to update server via API: {e}"
+        logger.error(error_msg, exc_info=True)
+        raise HTTPException(status_code=500, detail=error_msg)
     else:
-        logger.info("📬 Search index updated via API")
-
-    try:
-        if state.config and state.config.processor:
-            state.processor_config = configure_processor(state.config.processor)
-    except ValueError as e:
-        logger.error(e)
-        raise HTTPException(status_code=500, detail=str(e))
-    else:
-        logger.info("📬 Processor reconfigured via API")
+        components = []
+        if state.search_models:
+            components.append("Search models")
+        if state.content_index:
+            components.append("Content index")
+        if state.processor_config:
+            components.append("Conversation processor")
+        components_msg = ", ".join(components)
+        logger.info(f"📬 {components_msg} updated via API")
 
     update_telemetry_state(
         request=request,
diff --git a/src/khoj/search_type/text_search.py b/src/khoj/search_type/text_search.py
index a77be6e1..09174186 100644
--- a/src/khoj/search_type/text_search.py
+++ b/src/khoj/search_type/text_search.py
@@ -58,43 +58,48 @@ def extract_entries(jsonl_file) -> List[Entry]:
 
 
 def compute_embeddings(
-    entries_with_ids: List[Tuple[int, Entry]], bi_encoder: BaseEncoder, embeddings_file: Path, regenerate=False
+    entries_with_ids: List[Tuple[int, Entry]],
+    bi_encoder: BaseEncoder,
+    embeddings_file: Path,
+    regenerate=False,
+    normalize=True,
 ):
     "Compute (and Save) Embeddings or Load Pre-Computed Embeddings"
-    new_entries = []
+    new_embeddings = torch.tensor([], device=state.device)
+    existing_embeddings = torch.tensor([], device=state.device)
+    create_index_msg = ""
     # Load pre-computed embeddings from file if exists and update them if required
     if embeddings_file.exists() and not regenerate:
         corpus_embeddings: torch.Tensor = torch.load(get_absolute_path(embeddings_file), map_location=state.device)
         logger.debug(f"Loaded {len(corpus_embeddings)} text embeddings from {embeddings_file}")
-
-        # Encode any new entries in the corpus and update corpus embeddings
-        new_entries = [entry.compiled for id, entry in entries_with_ids if id == -1]
-        if new_entries:
-            logger.info(f"📩 Indexing {len(new_entries)} text entries.")
-            new_embeddings = bi_encoder.encode(
-                new_entries, convert_to_tensor=True, device=state.device, show_progress_bar=True
-            )
-            existing_entry_ids = [id for id, _ in entries_with_ids if id != -1]
-            if existing_entry_ids:
-                existing_embeddings = torch.index_select(
-                    corpus_embeddings, 0, torch.tensor(existing_entry_ids, device=state.device)
-                )
-            else:
-                existing_embeddings = torch.tensor([], device=state.device)
-            corpus_embeddings = torch.cat([existing_embeddings, new_embeddings], dim=0)
-    # Else compute the corpus embeddings from scratch
     else:
-        new_entries = [entry.compiled for _, entry in entries_with_ids]
-        logger.info(f"📩 Indexing {len(new_entries)} text entries. Creating index from scratch.")
-        corpus_embeddings = bi_encoder.encode(
+        corpus_embeddings = torch.tensor([], device=state.device)
+        create_index_msg = " Creating index from scratch."
+
+    # Encode any new entries in the corpus and update corpus embeddings
+    new_entries = [entry.compiled for id, entry in entries_with_ids if id == -1]
+    if new_entries:
+        logger.info(f"📩 Indexing {len(new_entries)} text entries.{create_index_msg}")
+        new_embeddings = bi_encoder.encode(
             new_entries, convert_to_tensor=True, device=state.device, show_progress_bar=True
         )
 
-    # Save regenerated or updated embeddings to file
-    if new_entries:
+    # Extract existing embeddings from previous corpus embeddings
+    existing_entry_ids = [id for id, _ in entries_with_ids if id != -1]
+    if existing_entry_ids:
+        existing_embeddings = torch.index_select(
+            corpus_embeddings, 0, torch.tensor(existing_entry_ids, device=state.device)
+        )
+
+    # Set corpus embeddings to merger of existing and new embeddings
+    corpus_embeddings = torch.cat([existing_embeddings, new_embeddings], dim=0)
+    if normalize:
+        # Normalize embeddings for faster lookup via dot product when querying
         corpus_embeddings = util.normalize_embeddings(corpus_embeddings)
-        torch.save(corpus_embeddings, embeddings_file)
-        logger.info(f"📩 Saved computed text embeddings to {embeddings_file}")
+
+    # Save regenerated or updated embeddings to file
+    torch.save(corpus_embeddings, embeddings_file)
+    logger.info(f"📩 Saved computed text embeddings to {embeddings_file}")
 
     return corpus_embeddings
 
@@ -173,13 +178,14 @@ def setup(
     bi_encoder: BaseEncoder,
     regenerate: bool,
     filters: List[BaseFilter] = [],
+    normalize: bool = True,
 ) -> TextContent:
     # Map notes in text files to (compressed) JSONL formatted file
     config.compressed_jsonl = resolve_absolute_path(config.compressed_jsonl)
-    previous_entries = (
-        extract_entries(config.compressed_jsonl) if config.compressed_jsonl.exists() and not regenerate else None
-    )
-    entries_with_indices = text_to_jsonl(config).process(previous_entries or [])
+    previous_entries = []
+    if config.compressed_jsonl.exists() and not regenerate:
+        previous_entries = extract_entries(config.compressed_jsonl)
+    entries_with_indices = text_to_jsonl(config).process(previous_entries)
 
     # Extract Updated Entries
     entries = extract_entries(config.compressed_jsonl)
@@ -190,7 +196,7 @@ def setup(
     # Compute or Load Embeddings
     config.embeddings_file = resolve_absolute_path(config.embeddings_file)
     corpus_embeddings = compute_embeddings(
-        entries_with_indices, bi_encoder, config.embeddings_file, regenerate=regenerate
+        entries_with_indices, bi_encoder, config.embeddings_file, regenerate=regenerate, normalize=normalize
     )
 
     for filter in filters:
diff --git a/src/khoj/utils/jsonl.py b/src/khoj/utils/jsonl.py
index c9576810..ed779e79 100644
--- a/src/khoj/utils/jsonl.py
+++ b/src/khoj/utils/jsonl.py
@@ -20,7 +20,7 @@ def load_jsonl(input_path):
     # Open JSONL file
     if input_path.suffix == ".gz":
         jsonl_file = gzip.open(get_absolute_path(input_path), "rt", encoding="utf-8")
-    elif input_path.suffix == ".jsonl":
+    else:
         jsonl_file = open(get_absolute_path(input_path), "r", encoding="utf-8")
 
     # Read JSONL file
@@ -36,17 +36,6 @@ def load_jsonl(input_path):
     return data
 
 
-def dump_jsonl(jsonl_data, output_path):
-    "Write List of JSON objects to JSON line file"
-    # Create output directory, if it doesn't exist
-    output_path.parent.mkdir(parents=True, exist_ok=True)
-
-    with open(output_path, "w", encoding="utf-8") as f:
-        f.write(jsonl_data)
-
-    logger.debug(f"Wrote jsonl data to {output_path}")
-
-
 def compress_jsonl_data(jsonl_data, output_path):
     # Create output directory, if it doesn't exist
     output_path.parent.mkdir(parents=True, exist_ok=True)
diff --git a/src/khoj/utils/state.py b/src/khoj/utils/state.py
index 89688e15..40b3daae 100644
--- a/src/khoj/utils/state.py
+++ b/src/khoj/utils/state.py
@@ -24,7 +24,7 @@ host: str = None
 port: int = None
 cli_args: List[str] = None
 query_cache = LRU()
-search_index_lock = threading.Lock()
+config_lock = threading.Lock()
 SearchType = utils_config.SearchType
 telemetry: List[Dict[str, str]] = []
 previous_query: str = None
diff --git a/tests/conftest.py b/tests/conftest.py
index a92d33ca..07c5156f 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -90,7 +90,7 @@ def content_config(tmp_path_factory, search_models: SearchModels, search_config:
     content_config.org = TextContentConfig(
         input_files=None,
         input_filter=["tests/data/org/*.org"],
-        compressed_jsonl=content_dir.joinpath("notes.jsonl"),
+        compressed_jsonl=content_dir.joinpath("notes.jsonl.gz"),
         embeddings_file=content_dir.joinpath("note_embeddings.pt"),
     )
 
@@ -101,7 +101,7 @@ def content_config(tmp_path_factory, search_models: SearchModels, search_config:
 
     content_config.plugins = {
         "plugin1": TextContentConfig(
-            input_files=[content_dir.joinpath("notes.jsonl")],
+            input_files=[content_dir.joinpath("notes.jsonl.gz")],
             input_filter=None,
             compressed_jsonl=content_dir.joinpath("plugin.jsonl.gz"),
             embeddings_file=content_dir.joinpath("plugin_embeddings.pt"),
@@ -142,7 +142,7 @@ def md_content_config(tmp_path_factory):
     content_config.markdown = TextContentConfig(
         input_files=None,
         input_filter=["tests/data/markdown/*.markdown"],
-        compressed_jsonl=content_dir.joinpath("markdown.jsonl"),
+        compressed_jsonl=content_dir.joinpath("markdown.jsonl.gz"),
         embeddings_file=content_dir.joinpath("markdown_embeddings.pt"),
     )
 
diff --git a/tests/test_text_search.py b/tests/test_text_search.py
index c18a4c42..1ae7e770 100644
--- a/tests/test_text_search.py
+++ b/tests/test_text_search.py
@@ -5,6 +5,7 @@ import os
 
 # External Packages
 import pytest
+import torch
 from khoj.utils.config import SearchModels
 
 # Internal Packages
@@ -17,7 +18,7 @@ from khoj.processor.github.github_to_jsonl import GithubToJsonl
 
 # Test
 # ----------------------------------------------------------------------------------------------------
-def test_asymmetric_setup_with_missing_file_raises_error(
+def test_text_search_setup_with_missing_file_raises_error(
     org_config_with_only_new_file: TextContentConfig, search_config: SearchConfig
 ):
     # Arrange
@@ -32,7 +33,7 @@ def test_asymmetric_setup_with_missing_file_raises_error(
 
 
 # ----------------------------------------------------------------------------------------------------
-def test_asymmetric_setup_with_empty_file_raises_error(
+def test_text_search_setup_with_empty_file_raises_error(
     org_config_with_only_new_file: TextContentConfig, search_config: SearchConfig
 ):
     # Act
@@ -42,7 +43,7 @@ def test_asymmetric_setup_with_empty_file_raises_error(
 
 
 # ----------------------------------------------------------------------------------------------------
-def test_asymmetric_setup(content_config: ContentConfig, search_models: SearchModels):
+def test_text_search_setup(content_config: ContentConfig, search_models: SearchModels):
     # Act
     # Regenerate notes embeddings during asymmetric setup
     notes_model = text_search.setup(
@@ -55,7 +56,7 @@ def test_asymmetric_setup(content_config: ContentConfig, search_models: SearchMo
 
 
 # ----------------------------------------------------------------------------------------------------
-def test_text_content_index_only_updates_on_changes(content_config: ContentConfig, search_models: SearchModels, caplog):
+def test_text_index_same_if_content_unchanged(content_config: ContentConfig, search_models: SearchModels, caplog):
     # Arrange
     caplog.set_level(logging.INFO, logger="khoj")
 
@@ -70,8 +71,8 @@ def test_text_content_index_only_updates_on_changes(content_config: ContentConfi
     final_logs = caplog.text
 
     # Assert
-    assert "📩 Saved computed text embeddings to" in initial_logs
-    assert "📩 Saved computed text embeddings to" not in final_logs
+    assert "Creating index from scratch." in initial_logs
+    assert "Creating index from scratch." not in final_logs
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -121,7 +122,9 @@ def test_entry_chunking_by_max_tokens(org_config_with_only_new_file: TextContent
 
 
 # ----------------------------------------------------------------------------------------------------
-def test_asymmetric_reload(content_config: ContentConfig, search_models: SearchModels, new_org_file: Path):
+def test_regenerate_index_with_new_entry(
+    content_config: ContentConfig, search_models: SearchModels, new_org_file: Path
+):
     # Arrange
     initial_notes_model = text_search.setup(
         OrgToJsonl, content_config.org, search_models.text_search.bi_encoder, regenerate=True
@@ -135,25 +138,20 @@ def test_asymmetric_reload(content_config: ContentConfig, search_models: SearchM
     with open(new_org_file, "w") as f:
         f.write("\n* A Chihuahua doing Tango\n- Saw a super cute video of a chihuahua doing the Tango on Youtube\n")
 
+    # Act
     # regenerate notes jsonl, model embeddings and model to include entry from new file
     regenerated_notes_model = text_search.setup(
         OrgToJsonl, content_config.org, search_models.text_search.bi_encoder, regenerate=True
     )
 
-    # Act
-    # reload embeddings, entries, notes model from previously generated notes jsonl and model embeddings files
-    initial_notes_model = text_search.setup(
-        OrgToJsonl, content_config.org, search_models.text_search.bi_encoder, regenerate=False
-    )
-
     # Assert
     assert len(regenerated_notes_model.entries) == 11
     assert len(regenerated_notes_model.corpus_embeddings) == 11
 
-    # Assert
-    # verify new entry loaded from updated embeddings, entries
-    assert len(initial_notes_model.entries) == 11
-    assert len(initial_notes_model.corpus_embeddings) == 11
+    # verify new entry appended to index, without disrupting order or content of existing entries
+    error_details = compare_index(initial_notes_model, regenerated_notes_model)
+    if error_details:
+        pytest.fail(error_details, False)
 
     # Cleanup
     # reset input_files in config to empty list
@@ -161,30 +159,101 @@ def test_asymmetric_reload(content_config: ContentConfig, search_models: SearchM
 
 
 # ----------------------------------------------------------------------------------------------------
-def test_incremental_update(content_config: ContentConfig, search_models: SearchModels, new_org_file: Path):
+def test_update_index_with_duplicate_entries_in_stable_order(
+    org_config_with_only_new_file: TextContentConfig, search_models: SearchModels
+):
     # Arrange
-    initial_notes_model = text_search.setup(
-        OrgToJsonl, content_config.org, search_models.text_search.bi_encoder, regenerate=True
+    new_file_to_index = Path(org_config_with_only_new_file.input_files[0])
+
+    # Insert org-mode entries with same compiled form into new org file
+    new_entry = "* TODO A Chihuahua doing Tango\n- Saw a super cute video of a chihuahua doing the Tango on Youtube\n"
+    with open(new_file_to_index, "w") as f:
+        f.write(f"{new_entry}{new_entry}")
+
+    # Act
+    # load embeddings, entries, notes model after adding new org-mode file
+    initial_index = text_search.setup(
+        OrgToJsonl, org_config_with_only_new_file, search_models.text_search.bi_encoder, regenerate=True
     )
 
-    assert len(initial_notes_model.entries) == 10
-    assert len(initial_notes_model.corpus_embeddings) == 10
+    # update embeddings, entries, notes model after adding new org-mode file
+    updated_index = text_search.setup(
+        OrgToJsonl, org_config_with_only_new_file, search_models.text_search.bi_encoder, regenerate=False
+    )
+
+    # Assert
+    # verify only 1 entry added even if there are multiple duplicate entries
+    assert len(initial_index.entries) == len(updated_index.entries) == 1
+    assert len(initial_index.corpus_embeddings) == len(updated_index.corpus_embeddings) == 1
+
+    # verify the same entry is added even when there are multiple duplicate entries
+    error_details = compare_index(initial_index, updated_index)
+    if error_details:
+        pytest.fail(error_details)
+
+
+# ----------------------------------------------------------------------------------------------------
+def test_update_index_with_deleted_entry(org_config_with_only_new_file: TextContentConfig, search_models: SearchModels):
+    # Arrange
+    new_file_to_index = Path(org_config_with_only_new_file.input_files[0])
+
+    # Insert org-mode entries with same compiled form into new org file
+    new_entry = "* TODO A Chihuahua doing Tango\n- Saw a super cute video of a chihuahua doing the Tango on Youtube\n"
+    with open(new_file_to_index, "w") as f:
+        f.write(f"{new_entry}{new_entry} -- Tatooine")
+
+    # load embeddings, entries, notes model after adding new org file with 2 entries
+    initial_index = text_search.setup(
+        OrgToJsonl, org_config_with_only_new_file, search_models.text_search.bi_encoder, regenerate=True
+    )
+
+    # update embeddings, entries, notes model after removing an entry from the org file
+    with open(new_file_to_index, "w") as f:
+        f.write(f"{new_entry}")
+
+    # Act
+    updated_index = text_search.setup(
+        OrgToJsonl, org_config_with_only_new_file, search_models.text_search.bi_encoder, regenerate=False
+    )
+
+    # Assert
+    # verify only 1 entry added even if there are multiple duplicate entries
+    assert len(initial_index.entries) == len(updated_index.entries) + 1
+    assert len(initial_index.corpus_embeddings) == len(updated_index.corpus_embeddings) + 1
+
+    # verify the same entry is added even when there are multiple duplicate entries
+    error_details = compare_index(updated_index, initial_index)
+    if error_details:
+        pytest.fail(error_details)
+
+
+# ----------------------------------------------------------------------------------------------------
+def test_update_index_with_new_entry(content_config: ContentConfig, search_models: SearchModels, new_org_file: Path):
+    # Arrange
+    initial_notes_model = text_search.setup(
+        OrgToJsonl, content_config.org, search_models.text_search.bi_encoder, regenerate=True, normalize=False
+    )
 
     # append org-mode entry to first org input file in config
     with open(new_org_file, "w") as f:
-        f.write("\n* A Chihuahua doing Tango\n- Saw a super cute video of a chihuahua doing the Tango on Youtube\n")
+        new_entry = "\n* A Chihuahua doing Tango\n- Saw a super cute video of a chihuahua doing the Tango on Youtube\n"
+        f.write(new_entry)
 
     # Act
     # update embeddings, entries with the newly added note
     content_config.org.input_files = [f"{new_org_file}"]
-    initial_notes_model = text_search.setup(
-        OrgToJsonl, content_config.org, search_models.text_search.bi_encoder, regenerate=False
+    final_notes_model = text_search.setup(
+        OrgToJsonl, content_config.org, search_models.text_search.bi_encoder, regenerate=False, normalize=False
     )
 
     # Assert
-    # verify new entry added in updated embeddings, entries
-    assert len(initial_notes_model.entries) == 11
-    assert len(initial_notes_model.corpus_embeddings) == 11
+    assert len(final_notes_model.entries) == len(initial_notes_model.entries) + 1
+    assert len(final_notes_model.corpus_embeddings) == len(initial_notes_model.corpus_embeddings) + 1
+
+    # verify new entry appended to index, without disrupting order or content of existing entries
+    error_details = compare_index(initial_notes_model, final_notes_model)
+    if error_details:
+        pytest.fail(error_details, False)
 
     # Cleanup
     # reset input_files in config to empty list
@@ -202,3 +271,25 @@ def test_asymmetric_setup_github(content_config: ContentConfig, search_models: S
 
     # Assert
     assert len(github_model.entries) > 1
+
+
+def compare_index(initial_notes_model, final_notes_model):
+    mismatched_entries, mismatched_embeddings = [], []
+    for index in range(len(initial_notes_model.entries)):
+        if initial_notes_model.entries[index].to_json() != final_notes_model.entries[index].to_json():
+            mismatched_entries.append(index)
+
+    # verify new entry embedding appended to embeddings tensor, without disrupting order or content of existing embeddings
+    for index in range(len(initial_notes_model.corpus_embeddings)):
+        if not torch.equal(final_notes_model.corpus_embeddings[index], initial_notes_model.corpus_embeddings[index]):
+            mismatched_embeddings.append(index)
+
+    error_details = ""
+    if mismatched_entries:
+        mismatched_entries_str = ",".join(map(str, mismatched_entries))
+        error_details += f"Entries at {mismatched_entries_str} not equal\n"
+    if mismatched_embeddings:
+        mismatched_embeddings_str = ", ".join(map(str, mismatched_embeddings))
+        error_details += f"Embeddings at {mismatched_embeddings_str} not equal\n"
+
+    return error_details