diff --git a/src/khoj/processor/conversation/anthropic/anthropic_chat.py b/src/khoj/processor/conversation/anthropic/anthropic_chat.py
index d5778885..ef8539b3 100644
--- a/src/khoj/processor/conversation/anthropic/anthropic_chat.py
+++ b/src/khoj/processor/conversation/anthropic/anthropic_chat.py
@@ -6,7 +6,7 @@ from typing import Dict, Optional
 
 from langchain.schema import ChatMessage
 
-from khoj.database.models import Agent
+from khoj.database.models import Agent, KhojUser
 from khoj.processor.conversation import prompts
 from khoj.processor.conversation.anthropic.utils import (
     anthropic_chat_completion_with_backoff,
@@ -24,14 +24,16 @@ def extract_questions_anthropic(
     model: Optional[str] = "claude-instant-1.2",
     conversation_log={},
     api_key=None,
-    temperature=0,
+    temperature=0.7,
     location_data: LocationData = None,
+    user: KhojUser = None,
 ):
     """
     Infer search queries to retrieve relevant notes to answer user query
     """
     # Extract Past User Message and Inferred Questions from Conversation Log
     location = f"{location_data.city}, {location_data.region}, {location_data.country}" if location_data else "Unknown"
+    username = prompts.user_name.format(name=user.get_full_name()) if user and user.get_full_name() else ""
 
     # Extract Past User Message and Inferred Questions from Conversation Log
     chat_history = "".join(
@@ -50,11 +52,13 @@ def extract_questions_anthropic(
     system_prompt = prompts.extract_questions_anthropic_system_prompt.format(
         current_date=today.strftime("%Y-%m-%d"),
         day_of_week=today.strftime("%A"),
+        current_month=today.strftime("%Y-%m"),
         last_new_year=last_new_year.strftime("%Y"),
         last_new_year_date=last_new_year.strftime("%Y-%m-%d"),
         current_new_year_date=current_new_year.strftime("%Y-%m-%d"),
         yesterday_date=(today - timedelta(days=1)).strftime("%Y-%m-%d"),
         location=location,
+        username=username,
     )
 
     prompt = prompts.extract_questions_anthropic_user_message.format(
diff --git a/src/khoj/processor/conversation/offline/chat_model.py b/src/khoj/processor/conversation/offline/chat_model.py
index 2da0c186..ec4c7367 100644
--- a/src/khoj/processor/conversation/offline/chat_model.py
+++ b/src/khoj/processor/conversation/offline/chat_model.py
@@ -7,7 +7,7 @@ from typing import Any, Iterator, List, Union
 from langchain.schema import ChatMessage
 from llama_cpp import Llama
 
-from khoj.database.models import Agent
+from khoj.database.models import Agent, KhojUser
 from khoj.processor.conversation import prompts
 from khoj.processor.conversation.offline.utils import download_model
 from khoj.processor.conversation.utils import (
@@ -30,7 +30,9 @@ def extract_questions_offline(
     use_history: bool = True,
     should_extract_questions: bool = True,
     location_data: LocationData = None,
+    user: KhojUser = None,
     max_prompt_size: int = None,
+    temperature: float = 0.7,
 ) -> List[str]:
     """
     Infer search queries to retrieve relevant notes to answer user query
@@ -45,6 +47,7 @@ def extract_questions_offline(
     offline_chat_model = loaded_model or download_model(model, max_tokens=max_prompt_size)
 
     location = f"{location_data.city}, {location_data.region}, {location_data.country}" if location_data else "Unknown"
+    username = prompts.user_name.format(name=user.get_full_name()) if user and user.get_full_name() else ""
 
     # Extract Past User Message and Inferred Questions from Conversation Log
     chat_history = ""
@@ -64,10 +67,12 @@ def extract_questions_offline(
         chat_history=chat_history,
         current_date=today.strftime("%Y-%m-%d"),
         day_of_week=today.strftime("%A"),
+        current_month=today.strftime("%Y-%m"),
         yesterday_date=yesterday,
         last_year=last_year,
         this_year=today.year,
         location=location,
+        username=username,
     )
 
     messages = generate_chatml_messages_with_context(
@@ -77,7 +82,11 @@ def extract_questions_offline(
     state.chat_lock.acquire()
     try:
         response = send_message_to_model_offline(
-            messages, loaded_model=offline_chat_model, model=model, max_prompt_size=max_prompt_size
+            messages,
+            loaded_model=offline_chat_model,
+            model=model,
+            max_prompt_size=max_prompt_size,
+            temperature=temperature,
         )
     finally:
         state.chat_lock.release()
@@ -229,6 +238,7 @@ def send_message_to_model_offline(
     messages: List[ChatMessage],
     loaded_model=None,
     model="NousResearch/Hermes-2-Pro-Mistral-7B-GGUF",
+    temperature: float = 0.2,
     streaming=False,
     stop=[],
     max_prompt_size: int = None,
@@ -236,7 +246,9 @@ def send_message_to_model_offline(
     assert loaded_model is None or isinstance(loaded_model, Llama), "loaded_model must be of type Llama, if configured"
     offline_chat_model = loaded_model or download_model(model, max_tokens=max_prompt_size)
     messages_dict = [{"role": message.role, "content": message.content} for message in messages]
-    response = offline_chat_model.create_chat_completion(messages_dict, stop=stop, stream=streaming)
+    response = offline_chat_model.create_chat_completion(
+        messages_dict, stop=stop, stream=streaming, temperature=temperature
+    )
     if streaming:
         return response
     else:
diff --git a/src/khoj/processor/conversation/openai/gpt.py b/src/khoj/processor/conversation/openai/gpt.py
index f1608fba..5dad883b 100644
--- a/src/khoj/processor/conversation/openai/gpt.py
+++ b/src/khoj/processor/conversation/openai/gpt.py
@@ -5,7 +5,7 @@ from typing import Dict, Optional
 
 from langchain.schema import ChatMessage
 
-from khoj.database.models import Agent
+from khoj.database.models import Agent, KhojUser
 from khoj.processor.conversation import prompts
 from khoj.processor.conversation.openai.utils import (
     chat_completion_with_backoff,
@@ -24,14 +24,15 @@ def extract_questions(
     conversation_log={},
     api_key=None,
     api_base_url=None,
-    temperature=0,
-    max_tokens=100,
+    temperature=0.7,
     location_data: LocationData = None,
+    user: KhojUser = None,
 ):
     """
     Infer search queries to retrieve relevant notes to answer user query
     """
     location = f"{location_data.city}, {location_data.region}, {location_data.country}" if location_data else "Unknown"
+    username = prompts.user_name.format(name=user.get_full_name()) if user and user.get_full_name() else ""
 
     # Extract Past User Message and Inferred Questions from Conversation Log
     chat_history = "".join(
@@ -50,6 +51,7 @@ def extract_questions(
     prompt = prompts.extract_questions.format(
         current_date=today.strftime("%Y-%m-%d"),
         day_of_week=today.strftime("%A"),
+        current_month=today.strftime("%Y-%m"),
         last_new_year=last_new_year.strftime("%Y"),
         last_new_year_date=last_new_year.strftime("%Y-%m-%d"),
         current_new_year_date=current_new_year.strftime("%Y-%m-%d"),
@@ -59,6 +61,7 @@ def extract_questions(
         text=text,
         yesterday_date=(today - timedelta(days=1)).strftime("%Y-%m-%d"),
         location=location,
+        username=username,
     )
     messages = [ChatMessage(content=prompt, role="user")]
 
diff --git a/src/khoj/processor/conversation/openai/utils.py b/src/khoj/processor/conversation/openai/utils.py
index bfc70482..314c3c1d 100644
--- a/src/khoj/processor/conversation/openai/utils.py
+++ b/src/khoj/processor/conversation/openai/utils.py
@@ -36,7 +36,7 @@ def completion_with_backoff(
     messages, model, temperature=0, openai_api_key=None, api_base_url=None, model_kwargs=None
 ) -> str:
     client_key = f"{openai_api_key}--{api_base_url}"
-    client: openai.OpenAI = openai_clients.get(client_key)
+    client: openai.OpenAI | None = openai_clients.get(client_key)
     if not client:
         client = openai.OpenAI(
             api_key=openai_api_key,
diff --git a/src/khoj/processor/conversation/prompts.py b/src/khoj/processor/conversation/prompts.py
index 289bafbc..6a8db9db 100644
--- a/src/khoj/processor/conversation/prompts.py
+++ b/src/khoj/processor/conversation/prompts.py
@@ -208,10 +208,12 @@ Construct search queries to retrieve relevant information to answer the user's q
 - Add as much context from the previous questions and answers as required into your search queries.
 - Break messages into multiple search queries when required to retrieve the relevant information.
 - Add date filters to your search queries from questions and answers when required to retrieve the relevant information.
+- When asked a meta, vague or random questions, search for a variety of broad topics to answer the user's question.
 - Share relevant search queries as a JSON list of strings. Do not say anything else.
 
 Current Date: {day_of_week}, {current_date}
 User's Location: {location}
+{username}
 
 Examples:
 Q: How was my trip to Cambodia?
@@ -238,6 +240,9 @@ Khoj: ["What kind of plants do I have?", "What issues do my plants have?"]
 Q: Who all did I meet here yesterday?
 Khoj: ["Met in {location} on {yesterday_date} dt>='{yesterday_date}' dt<'{current_date}'"]
 
+Q: Share some random, interesting experiences from this month
+Khoj: ["Exciting travel adventures from {current_month}", "Fun social events dt>='{current_month}-01' dt<'{current_date}'", "Intense emotional experiences in {current_month}"]
+
 Chat History:
 {chat_history}
 What searches will you perform to answer the following question, using the chat history as reference? Respond only with relevant search queries as a valid JSON list of strings.
@@ -254,10 +259,12 @@ Construct search queries to retrieve relevant information to answer the user's q
 - Add as much context from the previous questions and answers as required into your search queries.
 - Break messages into multiple search queries when required to retrieve the relevant information.
 - Add date filters to your search queries from questions and answers when required to retrieve the relevant information.
+- When asked a meta, vague or random questions, search for a variety of broad topics to answer the user's question.
 
 What searches will you perform to answer the users question? Respond with search queries as list of strings in a JSON object.
 Current Date: {day_of_week}, {current_date}
 User's Location: {location}
+{username}
 
 Q: How was my trip to Cambodia?
 Khoj: {{"queries": ["How was my trip to Cambodia?"]}}
@@ -279,6 +286,10 @@ Q: How many tennis balls fit in the back of a 2002 Honda Civic?
 Khoj: {{"queries": ["What is the size of a tennis ball?", "What is the trunk size of a 2002 Honda Civic?"]}}
 A: 1085 tennis balls will fit in the trunk of a Honda Civic
 
+Q: Share some random, interesting experiences from this month
+Khoj: {{"queries": ["Exciting travel adventures from {current_month}", "Fun social events dt>='{current_month}-01' dt<'{current_date}'", "Intense emotional experiences in {current_month}"]}}
+A: You had a great time at the local beach with your friends, attended a music concert and had a deep conversation with your friend, Khalid.
+
 Q: Is Bob older than Tom?
 Khoj: {{"queries": ["When was Bob born?", "What is Tom's age?"]}}
 A: Yes, Bob is older than Tom. As Bob was born on 1984-01-01 and Tom is 30 years old.
@@ -305,11 +316,13 @@ Construct search queries to retrieve relevant information to answer the user's q
 - Add as much context from the previous questions and answers as required into your search queries.
 - Break messages into multiple search queries when required to retrieve the relevant information.
 - Add date filters to your search queries from questions and answers when required to retrieve the relevant information.
+- When asked a meta, vague or random questions, search for a variety of broad topics to answer the user's question.
 
 What searches will you perform to answer the users question? Respond with a JSON object with the key "queries" mapping to a list of searches you would perform on the user's knowledge base. Just return the queries and nothing else.
 
 Current Date: {day_of_week}, {current_date}
 User's Location: {location}
+{username}
 
 Here are some examples of how you can construct search queries to answer the user's question:
 
@@ -328,6 +341,11 @@ A: I can help you live healthier and happier across work and personal life
 User: Who all did I meet here yesterday?
 Assistant: {{"queries": ["Met in {location} on {yesterday_date} dt>='{yesterday_date}' dt<'{current_date}'"]}}
 A: Yesterday's note mentions your visit to your local beach with Ram and Shyam.
+
+User: Share some random, interesting experiences from this month
+Assistant: {{"queries": ["Exciting travel adventures from {current_month}", "Fun social events dt>='{current_month}-01' dt<'{current_date}'", "Intense emotional experiences in {current_month}"]}}
+A: You had a great time at the local beach with your friends, attended a music concert and had a deep conversation with your friend, Khalid.
+
 """.strip()
 )
 
@@ -525,6 +543,7 @@ Which webpages will you need to read to answer the user's question?
 Provide web page links as a list of strings in a JSON object.
 Current Date: {current_date}
 User's Location: {location}
+{username}
 
 Here are some examples:
 History:
@@ -571,6 +590,7 @@ What Google searches, if any, will you need to perform to answer the user's ques
 Provide search queries as a list of strings in a JSON object. Do not wrap the json in a codeblock.
 Current Date: {current_date}
 User's Location: {location}
+{username}
 
 Here are some examples:
 History:
diff --git a/src/khoj/processor/tools/online_search.py b/src/khoj/processor/tools/online_search.py
index caf800b0..70e17630 100644
--- a/src/khoj/processor/tools/online_search.py
+++ b/src/khoj/processor/tools/online_search.py
@@ -10,6 +10,7 @@ import aiohttp
 from bs4 import BeautifulSoup
 from markdownify import markdownify
 
+from khoj.database.models import KhojUser
 from khoj.routers.helpers import (
     ChatEvent,
     extract_relevant_info,
@@ -51,6 +52,7 @@ async def search_online(
     query: str,
     conversation_history: dict,
     location: LocationData,
+    user: KhojUser,
     send_status_func: Optional[Callable] = None,
     custom_filters: List[str] = [],
 ):
@@ -61,7 +63,7 @@ async def search_online(
         return
 
     # Breakdown the query into subqueries to get the correct answer
-    subqueries = await generate_online_subqueries(query, conversation_history, location)
+    subqueries = await generate_online_subqueries(query, conversation_history, location, user)
     response_dict = {}
 
     if subqueries:
@@ -126,14 +128,18 @@ async def search_with_google(query: str) -> Tuple[str, Dict[str, List[Dict]]]:
 
 
 async def read_webpages(
-    query: str, conversation_history: dict, location: LocationData, send_status_func: Optional[Callable] = None
+    query: str,
+    conversation_history: dict,
+    location: LocationData,
+    user: KhojUser,
+    send_status_func: Optional[Callable] = None,
 ):
     "Infer web pages to read from the query and extract relevant information from them"
     logger.info(f"Inferring web pages to read")
     if send_status_func:
         async for event in send_status_func(f"**Inferring web pages to read**"):
             yield {ChatEvent.STATUS: event}
-    urls = await infer_webpage_urls(query, conversation_history, location)
+    urls = await infer_webpage_urls(query, conversation_history, location, user)
 
     logger.info(f"Reading web pages at: {urls}")
     if send_status_func:
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index 1c7697e5..953449d3 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -388,6 +388,7 @@ async def extract_references_and_questions(
                 conversation_log=meta_log,
                 should_extract_questions=True,
                 location_data=location_data,
+                user=user,
                 max_prompt_size=conversation_config.max_prompt_size,
             )
         elif conversation_config.model_type == ChatModelOptions.ModelType.OPENAI:
@@ -402,7 +403,7 @@ async def extract_references_and_questions(
                 api_base_url=base_url,
                 conversation_log=meta_log,
                 location_data=location_data,
-                max_tokens=conversation_config.max_prompt_size,
+                user=user,
             )
         elif conversation_config.model_type == ChatModelOptions.ModelType.ANTHROPIC:
             api_key = conversation_config.openai_config.api_key
@@ -413,6 +414,7 @@ async def extract_references_and_questions(
                 api_key=api_key,
                 conversation_log=meta_log,
                 location_data=location_data,
+                user=user,
             )
 
     # Collate search results as context for GPT
diff --git a/src/khoj/routers/api_chat.py b/src/khoj/routers/api_chat.py
index da0bd2d8..d515006c 100644
--- a/src/khoj/routers/api_chat.py
+++ b/src/khoj/routers/api_chat.py
@@ -792,7 +792,7 @@ async def chat(
         if ConversationCommand.Online in conversation_commands:
             try:
                 async for result in search_online(
-                    defiltered_query, meta_log, location, partial(send_event, ChatEvent.STATUS), custom_filters
+                    defiltered_query, meta_log, location, user, partial(send_event, ChatEvent.STATUS), custom_filters
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
                         yield result[ChatEvent.STATUS]
@@ -809,7 +809,7 @@ async def chat(
         if ConversationCommand.Webpage in conversation_commands:
             try:
                 async for result in read_webpages(
-                    defiltered_query, meta_log, location, partial(send_event, ChatEvent.STATUS)
+                    defiltered_query, meta_log, location, user, partial(send_event, ChatEvent.STATUS)
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
                         yield result[ChatEvent.STATUS]
diff --git a/src/khoj/routers/helpers.py b/src/khoj/routers/helpers.py
index 8d5a96ad..31b8d9b5 100644
--- a/src/khoj/routers/helpers.py
+++ b/src/khoj/routers/helpers.py
@@ -340,11 +340,14 @@ async def aget_relevant_output_modes(query: str, conversation_history: dict, is_
         return ConversationCommand.Text
 
 
-async def infer_webpage_urls(q: str, conversation_history: dict, location_data: LocationData) -> List[str]:
+async def infer_webpage_urls(
+    q: str, conversation_history: dict, location_data: LocationData, user: KhojUser
+) -> List[str]:
     """
     Infer webpage links from the given query
     """
     location = f"{location_data.city}, {location_data.region}, {location_data.country}" if location_data else "Unknown"
+    username = prompts.user_name.format(name=user.get_full_name()) if user.get_full_name() else ""
     chat_history = construct_chat_history(conversation_history)
 
     utc_date = datetime.utcnow().strftime("%Y-%m-%d")
@@ -353,6 +356,7 @@ async def infer_webpage_urls(q: str, conversation_history: dict, location_data:
         query=q,
         chat_history=chat_history,
         location=location,
+        username=username,
     )
 
     with timer("Chat actor: Infer webpage urls to read", logger):
@@ -370,11 +374,14 @@ async def infer_webpage_urls(q: str, conversation_history: dict, location_data:
         raise ValueError(f"Invalid list of urls: {response}")
 
 
-async def generate_online_subqueries(q: str, conversation_history: dict, location_data: LocationData) -> List[str]:
+async def generate_online_subqueries(
+    q: str, conversation_history: dict, location_data: LocationData, user: KhojUser
+) -> List[str]:
     """
     Generate subqueries from the given query
     """
     location = f"{location_data.city}, {location_data.region}, {location_data.country}" if location_data else "Unknown"
+    username = prompts.user_name.format(name=user.get_full_name()) if user.get_full_name() else ""
     chat_history = construct_chat_history(conversation_history)
 
     utc_date = datetime.utcnow().strftime("%Y-%m-%d")
@@ -383,6 +390,7 @@ async def generate_online_subqueries(q: str, conversation_history: dict, locatio
         query=q,
         chat_history=chat_history,
         location=location,
+        username=username,
     )
 
     with timer("Chat actor: Generate online search subqueries", logger):
diff --git a/tests/test_openai_chat_actors.py b/tests/test_openai_chat_actors.py
index ae2a8c55..83aee27f 100644
--- a/tests/test_openai_chat_actors.py
+++ b/tests/test_openai_chat_actors.py
@@ -17,6 +17,7 @@ from khoj.routers.helpers import (
 )
 from khoj.utils.helpers import ConversationCommand
 from khoj.utils.rawconfig import LocationData
+from tests.conftest import default_user2
 
 # Initialize variables for tests
 api_key = os.getenv("OPENAI_API_KEY")
@@ -412,18 +413,23 @@ def test_answer_general_question_not_in_chat_history_or_retrieved_content():
 
 
 # ----------------------------------------------------------------------------------------------------
-@pytest.mark.xfail(reason="Chat actor not consistently capable of asking for clarification yet.")
 @pytest.mark.chatquality
 def test_ask_for_clarification_if_not_enough_context_in_question():
     "Chat actor should ask for clarification if question cannot be answered unambiguously with the provided context"
     # Arrange
     context = [
-        f"""# Ramya
-My sister, Ramya, is married to Kali Devi. They have 2 kids, Ravi and Rani.""",
-        f"""# Fang
-My sister, Fang Liu is married to Xi Li. They have 1 kid, Xiao Li.""",
-        f"""# Aiyla
-My sister, Aiyla is married to Tolga. They have 3 kids, Yildiz, Ali and Ahmet.""",
+        {
+            "compiled": f"""# Ramya
+My sister, Ramya, is married to Kali Devi. They have 2 kids, Ravi and Rani."""
+        },
+        {
+            "compiled": f"""# Fang
+My sister, Fang Liu is married to Xi Li. They have 1 kid, Xiao Li."""
+        },
+        {
+            "compiled": f"""# Aiyla
+My sister, Aiyla is married to Tolga. They have 3 kids, Yildiz, Ali and Ahmet."""
+        },
     ]
 
     # Act
@@ -481,12 +487,12 @@ def test_agent_prompt_should_be_used(openai_agent):
 @pytest.mark.anyio
 @pytest.mark.django_db(transaction=True)
 @freeze_time("2024-04-04", ignore=["transformers"])
-async def test_websearch_with_operators(chat_client):
+async def test_websearch_with_operators(chat_client, default_user2):
     # Arrange
     user_query = "Share popular posts on r/worldnews this month"
 
     # Act
-    responses = await generate_online_subqueries(user_query, {}, None)
+    responses = await generate_online_subqueries(user_query, {}, None, default_user2)
 
     # Assert
     assert any(
@@ -501,12 +507,12 @@ async def test_websearch_with_operators(chat_client):
 # ----------------------------------------------------------------------------------------------------
 @pytest.mark.anyio
 @pytest.mark.django_db(transaction=True)
-async def test_websearch_khoj_website_for_info_about_khoj(chat_client):
+async def test_websearch_khoj_website_for_info_about_khoj(chat_client, default_user2):
     # Arrange
     user_query = "Do you support image search?"
 
     # Act
-    responses = await generate_online_subqueries(user_query, {}, None)
+    responses = await generate_online_subqueries(user_query, {}, None, default_user2)
 
     # Assert
     assert any(
@@ -558,12 +564,12 @@ async def test_select_data_sources_actor_chooses_to_search_notes(
 # ----------------------------------------------------------------------------------------------------
 @pytest.mark.anyio
 @pytest.mark.django_db(transaction=True)
-async def test_infer_webpage_urls_actor_extracts_correct_links(chat_client):
+async def test_infer_webpage_urls_actor_extracts_correct_links(chat_client, default_user2):
     # Arrange
     user_query = "Summarize the wikipedia page on the history of the internet"
 
     # Act
-    urls = await infer_webpage_urls(user_query, {}, None)
+    urls = await infer_webpage_urls(user_query, {}, None, default_user2)
 
     # Assert
     assert "https://en.wikipedia.org/wiki/History_of_the_Internet" in urls
@@ -667,6 +673,10 @@ def populate_chat_history(message_list):
         conversation_log["chat"] += message_to_log(
             user_message,
             gpt_message,
-            {"context": context, "intent": {"query": user_message, "inferred-queries": f'["{user_message}"]'}},
+            khoj_message_metadata={
+                "context": context,
+                "intent": {"query": user_message, "inferred-queries": f'["{user_message}"]'},
+            },
+            conversation_log=[],
         )
     return conversation_log