diff --git a/src/khoj/processor/conversation/utils.py b/src/khoj/processor/conversation/utils.py
index c6b3bc2f..0aaaa4b3 100644
--- a/src/khoj/processor/conversation/utils.py
+++ b/src/khoj/processor/conversation/utils.py
@@ -112,6 +112,7 @@ class InformationCollectionIteration:
         onlineContext: dict = None,
         codeContext: dict = None,
         summarizedResult: str = None,
+        warning: str = None,
     ):
         self.tool = tool
         self.query = query
@@ -119,6 +120,7 @@ class InformationCollectionIteration:
         self.onlineContext = onlineContext
         self.codeContext = codeContext
         self.summarizedResult = summarizedResult
+        self.warning = warning
 
 
 def construct_iteration_history(
diff --git a/src/khoj/processor/tools/online_search.py b/src/khoj/processor/tools/online_search.py
index 34c4911a..d2d8c685 100644
--- a/src/khoj/processor/tools/online_search.py
+++ b/src/khoj/processor/tools/online_search.py
@@ -4,7 +4,7 @@ import logging
 import os
 import urllib.parse
 from collections import defaultdict
-from typing import Any, Callable, Dict, List, Optional, Tuple, Union
+from typing import Any, Callable, Dict, List, Optional, Set, Tuple, Union
 
 import aiohttp
 from bs4 import BeautifulSoup
@@ -66,6 +66,7 @@ async def search_online(
     custom_filters: List[str] = [],
     max_webpages_to_read: int = DEFAULT_MAX_WEBPAGES_TO_READ,
     query_images: List[str] = None,
+    previous_subqueries: Set = set(),
     agent: Agent = None,
     tracer: dict = {},
 ):
@@ -76,19 +77,24 @@ async def search_online(
         return
 
     # Breakdown the query into subqueries to get the correct answer
-    subqueries = await generate_online_subqueries(
+    new_subqueries = await generate_online_subqueries(
         query, conversation_history, location, user, query_images=query_images, agent=agent, tracer=tracer
     )
-    response_dict = {}
+    subqueries = list(new_subqueries - previous_subqueries)
+    response_dict: Dict[str, Dict[str, List[Dict] | Dict]] = {}
 
-    if subqueries:
-        logger.info(f"🌐 Searching the Internet for {list(subqueries)}")
-        if send_status_func:
-            subqueries_str = "\n- " + "\n- ".join(list(subqueries))
-            async for event in send_status_func(f"**Searching the Internet for**: {subqueries_str}"):
-                yield {ChatEvent.STATUS: event}
+    if is_none_or_empty(subqueries):
+        logger.info("No new subqueries to search online")
+        yield response_dict
+        return
 
-    with timer(f"Internet searches for {list(subqueries)} took", logger):
+    logger.info(f"🌐 Searching the Internet for {subqueries}")
+    if send_status_func:
+        subqueries_str = "\n- " + "\n- ".join(subqueries)
+        async for event in send_status_func(f"**Searching the Internet for**: {subqueries_str}"):
+            yield {ChatEvent.STATUS: event}
+
+    with timer(f"Internet searches for {subqueries} took", logger):
         search_func = search_with_google if SERPER_DEV_API_KEY else search_with_jina
         search_tasks = [search_func(subquery, location) for subquery in subqueries]
         search_results = await asyncio.gather(*search_tasks)
@@ -119,7 +125,9 @@ async def search_online(
             async for event in send_status_func(f"**Reading web pages**: {webpage_links_str}"):
                 yield {ChatEvent.STATUS: event}
     tasks = [
-        read_webpage_and_extract_content(data["queries"], link, data["content"], user=user, agent=agent, tracer=tracer)
+        read_webpage_and_extract_content(
+            data["queries"], link, data.get("content"), user=user, agent=agent, tracer=tracer
+        )
         for link, data in webpages.items()
     ]
     results = await asyncio.gather(*tasks)
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index bed7c27b..3eb2dea5 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -6,7 +6,7 @@ import os
 import threading
 import time
 import uuid
-from typing import Any, Callable, List, Optional, Union
+from typing import Any, Callable, List, Optional, Set, Union
 
 import cron_descriptor
 import pytz
@@ -349,6 +349,7 @@ async def extract_references_and_questions(
     location_data: LocationData = None,
     send_status_func: Optional[Callable] = None,
     query_images: Optional[List[str]] = None,
+    previous_inferred_queries: Set = set(),
     agent: Agent = None,
     tracer: dict = {},
 ):
@@ -477,6 +478,7 @@ async def extract_references_and_questions(
             )
 
     # Collate search results as context for GPT
+    inferred_queries = list(set(inferred_queries) - previous_inferred_queries)
     with timer("Searching knowledge base took", logger):
         search_results = []
         logger.info(f"🔍 Searching knowledge base with queries: {inferred_queries}")
diff --git a/src/khoj/routers/api_chat.py b/src/khoj/routers/api_chat.py
index 8646a695..c30f4cf8 100644
--- a/src/khoj/routers/api_chat.py
+++ b/src/khoj/routers/api_chat.py
@@ -778,7 +778,8 @@ async def chat(
                     yield research_result
 
             # researched_results = await extract_relevant_info(q, researched_results, agent)
-            logger.info(f"Researched Results: {researched_results}")
+            if state.verbose > 1:
+                logger.debug(f"Researched Results: {researched_results}")
 
         used_slash_summarize = conversation_commands == [ConversationCommand.Summarize]
         file_filters = conversation.file_filters if conversation else []
diff --git a/src/khoj/routers/helpers.py b/src/khoj/routers/helpers.py
index c7a90fc3..d89ed147 100644
--- a/src/khoj/routers/helpers.py
+++ b/src/khoj/routers/helpers.py
@@ -20,6 +20,7 @@ from typing import (
     Iterator,
     List,
     Optional,
+    Set,
     Tuple,
     Union,
 )
@@ -494,7 +495,7 @@ async def generate_online_subqueries(
     query_images: List[str] = None,
     agent: Agent = None,
     tracer: dict = {},
-) -> List[str]:
+) -> Set[str]:
     """
     Generate subqueries from the given query
     """
@@ -529,14 +530,14 @@ async def generate_online_subqueries(
     try:
         response = clean_json(response)
         response = json.loads(response)
-        response = [q.strip() for q in response["queries"] if q.strip()]
-        if not isinstance(response, list) or not response or len(response) == 0:
+        response = {q.strip() for q in response["queries"] if q.strip()}
+        if not isinstance(response, set) or not response or len(response) == 0:
             logger.error(f"Invalid response for constructing subqueries: {response}. Returning original query: {q}")
-            return [q]
+            return {q}
         return response
     except Exception as e:
         logger.error(f"Invalid response for constructing subqueries: {response}. Returning original query: {q}")
-        return [q]
+        return {q}
 
 
 async def schedule_query(
@@ -1128,9 +1129,6 @@ def generate_chat_response(
 
     metadata = {}
     agent = AgentAdapters.get_conversation_agent_by_id(conversation.agent.id) if conversation.agent else None
-    query_to_run = q
-    if meta_research:
-        query_to_run = f"AI Research: {meta_research} {q}"
     try:
         partial_completion = partial(
             save_to_conversation_log,
@@ -1148,6 +1146,13 @@ def generate_chat_response(
             train_of_thought=train_of_thought,
         )
 
+        query_to_run = q
+        if meta_research:
+            query_to_run = f"<query>{q}</query>\n<collected_research>\n{meta_research}\n</collected_research>"
+            compiled_references = []
+            online_results = {}
+            code_results = {}
+
         conversation_config = ConversationAdapters.get_valid_conversation_config(user, conversation)
         vision_available = conversation_config.vision_enabled
         if not vision_available and query_images:
diff --git a/src/khoj/routers/research.py b/src/khoj/routers/research.py
index 46d4c424..1caf7c96 100644
--- a/src/khoj/routers/research.py
+++ b/src/khoj/routers/research.py
@@ -43,38 +43,35 @@ async def apick_next_tool(
     location: LocationData = None,
     user_name: str = None,
     agent: Agent = None,
-    previous_iterations_history: str = None,
+    previous_iterations: List[InformationCollectionIteration] = [],
     max_iterations: int = 5,
     send_status_func: Optional[Callable] = None,
     tracer: dict = {},
 ):
-    """
-    Given a query, determine which of the available tools the agent should use in order to answer appropriately. One at a time, and it's able to use subsequent iterations to refine the answer.
-    """
+    """Given a query, determine which of the available tools the agent should use in order to answer appropriately."""
 
+    # Construct tool options for the agent to choose from
     tool_options = dict()
     tool_options_str = ""
-
     agent_tools = agent.input_tools if agent else []
-
     for tool, description in function_calling_description_for_llm.items():
         tool_options[tool.value] = description
         if len(agent_tools) == 0 or tool.value in agent_tools:
             tool_options_str += f'- "{tool.value}": "{description}"\n'
 
+    # Construct chat history with user and iteration history with researcher agent for context
     chat_history = construct_chat_history(conversation_history, agent_name=agent.name if agent else "Khoj")
+    previous_iterations_history = construct_iteration_history(previous_iterations, prompts.previous_iteration)
 
     if query_images:
         query = f"[placeholder for user attached images]\n{query}"
 
+    today = datetime.today()
+    location_data = f"{location}" if location else "Unknown"
     personality_context = (
         prompts.personality_context.format(personality=agent.personality) if agent and agent.personality else ""
     )
 
-    # Extract Past User Message and Inferred Questions from Conversation Log
-    today = datetime.today()
-    location_data = f"{location}" if location else "Unknown"
-
     function_planning_prompt = prompts.plan_function_execution.format(
         tools=tool_options_str,
         chat_history=chat_history,
@@ -112,8 +109,15 @@ async def apick_next_tool(
         selected_tool = response.get("tool", None)
         generated_query = response.get("query", None)
         scratchpad = response.get("scratchpad", None)
+        warning = None
         logger.info(f"Response for determining relevant tools: {response}")
-        if send_status_func:
+
+        # Detect selection of previously used query, tool combination.
+        previous_tool_query_combinations = {(i.tool, i.query) for i in previous_iterations}
+        if (selected_tool, generated_query) in previous_tool_query_combinations:
+            warning = f"Repeated tool, query combination detected. Skipping iteration. Try something different."
+        # Only send client status updates if we'll execute this iteration
+        elif send_status_func:
             determined_tool_message = "**Determined Tool**: "
             determined_tool_message += f"{selected_tool}({generated_query})." if selected_tool else "respond."
             determined_tool_message += f"\nReason: {scratchpad}" if scratchpad else ""
@@ -123,13 +127,14 @@ async def apick_next_tool(
         yield InformationCollectionIteration(
             tool=selected_tool,
             query=generated_query,
+            warning=warning,
         )
-
     except Exception as e:
         logger.error(f"Invalid response for determining relevant tools: {response}. {e}", exc_info=True)
         yield InformationCollectionIteration(
             tool=None,
             query=None,
+            warning=f"Invalid response for determining relevant tools: {response}. Skipping iteration. Fix error: {e}",
         )
 
 
@@ -156,7 +161,6 @@ async def execute_information_collection(
         document_results: List[Dict[str, str]] = []
         summarize_files: str = ""
         this_iteration = InformationCollectionIteration(tool=None, query=query)
-        previous_iterations_history = construct_iteration_history(previous_iterations, prompts.previous_iteration)
 
         async for result in apick_next_tool(
             query,
@@ -166,7 +170,7 @@ async def execute_information_collection(
             location,
             user_name,
             agent,
-            previous_iterations_history,
+            previous_iterations,
             MAX_ITERATIONS,
             send_status_func,
             tracer=tracer,
@@ -176,9 +180,16 @@ async def execute_information_collection(
             elif isinstance(result, InformationCollectionIteration):
                 this_iteration = result
 
-        if this_iteration.tool == ConversationCommand.Notes:
+        # Skip running iteration if warning present in iteration
+        if this_iteration.warning:
+            logger.warning(f"Research mode: {this_iteration.warning}.")
+
+        elif this_iteration.tool == ConversationCommand.Notes:
             this_iteration.context = []
             document_results = []
+            previous_inferred_queries = {
+                c["query"] for iteration in previous_iterations if iteration.context for c in iteration.context
+            }
             async for result in extract_references_and_questions(
                 request,
                 construct_tool_chat_history(previous_iterations, ConversationCommand.Notes),
@@ -190,6 +201,7 @@ async def execute_information_collection(
                 location,
                 send_status_func,
                 query_images,
+                previous_inferred_queries=previous_inferred_queries,
                 agent=agent,
                 tracer=tracer,
             ):
@@ -213,6 +225,12 @@ async def execute_information_collection(
                     logger.error(f"Error extracting document references: {e}", exc_info=True)
 
         elif this_iteration.tool == ConversationCommand.Online:
+            previous_subqueries = {
+                subquery
+                for iteration in previous_iterations
+                if iteration.onlineContext
+                for subquery in iteration.onlineContext.keys()
+            }
             async for result in search_online(
                 this_iteration.query,
                 construct_tool_chat_history(previous_iterations, ConversationCommand.Online),
@@ -222,11 +240,16 @@ async def execute_information_collection(
                 [],
                 max_webpages_to_read=0,
                 query_images=query_images,
+                previous_subqueries=previous_subqueries,
                 agent=agent,
                 tracer=tracer,
             ):
                 if isinstance(result, dict) and ChatEvent.STATUS in result:
                     yield result[ChatEvent.STATUS]
+                elif is_none_or_empty(result):
+                    this_iteration.warning = (
+                        "Detected previously run online search queries. Skipping iteration. Try something different."
+                    )
                 else:
                     online_results: Dict[str, Dict] = result  # type: ignore
                     this_iteration.onlineContext = online_results
@@ -311,16 +334,19 @@ async def execute_information_collection(
 
         current_iteration += 1
 
-        if document_results or online_results or code_results or summarize_files:
-            results_data = f"**Results**:\n"
+        if document_results or online_results or code_results or summarize_files or this_iteration.warning:
+            results_data = f"\n<iteration>{current_iteration}\n<tool>{this_iteration.tool}</tool>\n<query>{this_iteration.query}</query>\n<results>"
             if document_results:
-                results_data += f"**Document References**:\n{yaml.dump(document_results, allow_unicode=True, sort_keys=False, default_flow_style=False)}\n"
+                results_data += f"\n<document_references>\n{yaml.dump(document_results, allow_unicode=True, sort_keys=False, default_flow_style=False)}\n</document_references>"
             if online_results:
-                results_data += f"**Online Results**:\n{yaml.dump(online_results, allow_unicode=True, sort_keys=False, default_flow_style=False)}\n"
+                results_data += f"\n<online_results>\n{yaml.dump(online_results, allow_unicode=True, sort_keys=False, default_flow_style=False)}\n</online_results>"
             if code_results:
-                results_data += f"**Code Results**:\n{yaml.dump(code_results, allow_unicode=True, sort_keys=False, default_flow_style=False)}\n"
+                results_data += f"\n<code_results>\n{yaml.dump(code_results, allow_unicode=True, sort_keys=False, default_flow_style=False)}\n</code_results>"
             if summarize_files:
-                results_data += f"**Summarized Files**:\n{yaml.dump(summarize_files, allow_unicode=True, sort_keys=False, default_flow_style=False)}\n"
+                results_data += f"\n<summarized_files>\n{yaml.dump(summarize_files, allow_unicode=True, sort_keys=False, default_flow_style=False)}\n</summarized_files>"
+            if this_iteration.warning:
+                results_data += f"\n<warning>\n{this_iteration.warning}\n</warning>"
+            results_data += "\n</results>\n</iteration>"
 
             # intermediate_result = await extract_relevant_info(this_iteration.query, results_data, agent)
             this_iteration.summarizedResult = results_data