diff --git a/src/khoj/database/models/__init__.py b/src/khoj/database/models/__init__.py
index 34538df0..2c5f0ada 100644
--- a/src/khoj/database/models/__init__.py
+++ b/src/khoj/database/models/__init__.py
@@ -107,7 +107,7 @@ class ChatMessage(PydanticBaseModel):
     onlineContext: Dict[str, OnlineContext] = {}
     codeContext: Dict[str, CodeContextData] = {}
     researchContext: Optional[List] = None
-    operatorContext: Optional[Dict[str, str]] = None
+    operatorContext: Optional[List] = None
     created: str
     images: Optional[List[str]] = None
     queryFiles: Optional[List[Dict]] = None
diff --git a/src/khoj/processor/conversation/anthropic/anthropic_chat.py b/src/khoj/processor/conversation/anthropic/anthropic_chat.py
index e2de2c59..2e52a9f2 100644
--- a/src/khoj/processor/conversation/anthropic/anthropic_chat.py
+++ b/src/khoj/processor/conversation/anthropic/anthropic_chat.py
@@ -14,6 +14,7 @@ from khoj.processor.conversation.anthropic.utils import (
     format_messages_for_anthropic,
 )
 from khoj.processor.conversation.utils import (
+    OperatorRun,
     ResponseWithThought,
     clean_json,
     construct_structured_message,
@@ -144,7 +145,7 @@ async def converse_anthropic(
     references: list[dict],
     online_results: Optional[Dict[str, Dict]] = None,
     code_results: Optional[Dict[str, Dict]] = None,
-    operator_results: Optional[Dict[str, str]] = None,
+    operator_results: Optional[List[OperatorRun]] = None,
     conversation_log={},
     model: Optional[str] = "claude-3-7-sonnet-latest",
     api_key: Optional[str] = None,
@@ -216,8 +217,11 @@ async def converse_anthropic(
             f"{prompts.code_executed_context.format(code_results=truncate_code_context(code_results))}\n\n"
         )
     if ConversationCommand.Operator in conversation_commands and not is_none_or_empty(operator_results):
+        operator_content = [
+            {"query": oc.query, "response": oc.response, "webpages": oc.webpages} for oc in operator_results
+        ]
         context_message += (
-            f"{prompts.operator_execution_context.format(operator_results=yaml_dump(operator_results))}\n\n"
+            f"{prompts.operator_execution_context.format(operator_results=yaml_dump(operator_content))}\n\n"
         )
     context_message = context_message.strip()
 
diff --git a/src/khoj/processor/conversation/google/gemini_chat.py b/src/khoj/processor/conversation/google/gemini_chat.py
index 6cbe87c8..17bb9b76 100644
--- a/src/khoj/processor/conversation/google/gemini_chat.py
+++ b/src/khoj/processor/conversation/google/gemini_chat.py
@@ -14,6 +14,7 @@ from khoj.processor.conversation.google.utils import (
     gemini_completion_with_backoff,
 )
 from khoj.processor.conversation.utils import (
+    OperatorRun,
     clean_json,
     construct_structured_message,
     generate_chatml_messages_with_context,
@@ -166,7 +167,7 @@ async def converse_gemini(
     references: list[dict],
     online_results: Optional[Dict[str, Dict]] = None,
     code_results: Optional[Dict[str, Dict]] = None,
-    operator_results: Optional[Dict[str, str]] = None,
+    operator_results: Optional[List[OperatorRun]] = None,
     conversation_log={},
     model: Optional[str] = "gemini-2.0-flash",
     api_key: Optional[str] = None,
@@ -240,8 +241,11 @@ async def converse_gemini(
             f"{prompts.code_executed_context.format(code_results=truncate_code_context(code_results))}\n\n"
         )
     if ConversationCommand.Operator in conversation_commands and not is_none_or_empty(operator_results):
+        operator_content = [
+            {"query": oc.query, "response": oc.response, "webpages": oc.webpages} for oc in operator_results
+        ]
         context_message += (
-            f"{prompts.operator_execution_context.format(operator_results=yaml_dump(operator_results))}\n\n"
+            f"{prompts.operator_execution_context.format(operator_results=yaml_dump(operator_content))}\n\n"
         )
     context_message = context_message.strip()
 
diff --git a/src/khoj/processor/conversation/openai/gpt.py b/src/khoj/processor/conversation/openai/gpt.py
index 28739843..d5fcd0a1 100644
--- a/src/khoj/processor/conversation/openai/gpt.py
+++ b/src/khoj/processor/conversation/openai/gpt.py
@@ -17,6 +17,7 @@ from khoj.processor.conversation.openai.utils import (
 )
 from khoj.processor.conversation.utils import (
     JsonSupport,
+    OperatorRun,
     ResponseWithThought,
     clean_json,
     construct_structured_message,
@@ -169,7 +170,7 @@ async def converse_openai(
     references: list[dict],
     online_results: Optional[Dict[str, Dict]] = None,
     code_results: Optional[Dict[str, Dict]] = None,
-    operator_results: Optional[Dict[str, str]] = None,
+    operator_results: Optional[List[OperatorRun]] = None,
     conversation_log={},
     model: str = "gpt-4o-mini",
     api_key: Optional[str] = None,
@@ -242,8 +243,11 @@ async def converse_openai(
             f"{prompts.code_executed_context.format(code_results=truncate_code_context(code_results))}\n\n"
         )
     if not is_none_or_empty(operator_results):
+        operator_content = [
+            {"query": oc.query, "response": oc.response, "webpages": oc.webpages} for oc in operator_results
+        ]
         context_message += (
-            f"{prompts.operator_execution_context.format(operator_results=yaml_dump(operator_results))}\n\n"
+            f"{prompts.operator_execution_context.format(operator_results=yaml_dump(operator_content))}\n\n"
         )
 
     context_message = context_message.strip()
diff --git a/src/khoj/processor/conversation/utils.py b/src/khoj/processor/conversation/utils.py
index 36aa001d..899a6786 100644
--- a/src/khoj/processor/conversation/utils.py
+++ b/src/khoj/processor/conversation/utils.py
@@ -10,7 +10,7 @@ from dataclasses import dataclass
 from datetime import datetime
 from enum import Enum
 from io import BytesIO
-from typing import Any, Callable, Dict, List, Optional
+from typing import Any, Callable, Dict, List, Literal, Optional, Union
 
 import PIL.Image
 import pyjson5
@@ -20,6 +20,7 @@ import yaml
 from langchain_core.messages.chat import ChatMessage
 from llama_cpp import LlamaTokenizer
 from llama_cpp.llama import Llama
+from pydantic import BaseModel
 from transformers import AutoTokenizer, PreTrainedTokenizer, PreTrainedTokenizerFast
 
 from khoj.database.adapters import ConversationAdapters
@@ -87,6 +88,48 @@ model_to_prompt_size = {
 model_to_tokenizer: Dict[str, str] = {}
 
 
+class AgentMessage(BaseModel):
+    role: Literal["user", "assistant", "system", "environment"]
+    content: Union[str, List]
+
+
+class OperatorRun:
+    def __init__(
+        self,
+        query: str,
+        trajectory: list[AgentMessage | dict] = None,
+        response: str = None,
+        webpages: list[dict] = None,
+    ):
+        self.query = query
+        self.response = response
+        self.webpages = webpages or []
+        self.trajectory: list[AgentMessage] = []
+        if trajectory:
+            for item in trajectory:
+                if isinstance(item, dict):
+                    self.trajectory.append(AgentMessage(**item))
+                elif hasattr(item, "role") and hasattr(item, "content"):  # Heuristic for AgentMessage like object
+                    self.trajectory.append(item)
+                else:
+                    logger.warning(f"Unexpected item type in trajectory: {type(item)}")
+
+    def to_dict(self) -> dict:
+        # Ensure AgentMessage instances in trajectory are also dicts
+        serialized_trajectory = []
+        for msg in self.trajectory:
+            if hasattr(msg, "model_dump"):  # Check if it's a Pydantic model
+                serialized_trajectory.append(msg.model_dump())
+            elif isinstance(msg, dict):
+                serialized_trajectory.append(msg)  # Already a dict
+        return {
+            "query": self.query,
+            "response": self.response,
+            "trajectory": serialized_trajectory,
+            "webpages": self.webpages,
+        }
+
+
 class InformationCollectionIteration:
     def __init__(
         self,
@@ -95,7 +138,7 @@ class InformationCollectionIteration:
         context: list = None,
         onlineContext: dict = None,
         codeContext: dict = None,
-        operatorContext: dict[str, str] = None,
+        operatorContext: dict = None,
         summarizedResult: str = None,
         warning: str = None,
     ):
@@ -104,10 +147,17 @@ class InformationCollectionIteration:
         self.context = context
         self.onlineContext = onlineContext
         self.codeContext = codeContext
-        self.operatorContext = operatorContext
+        self.operatorContext = OperatorRun(**operatorContext) if isinstance(operatorContext, dict) else None
         self.summarizedResult = summarizedResult
         self.warning = warning
 
+    def to_dict(self) -> dict:
+        data = vars(self).copy()
+        data["operatorContext"] = (
+            self.operatorContext.to_dict() if isinstance(self.operatorContext, OperatorRun) else None
+        )
+        return data
+
 
 def construct_iteration_history(
     previous_iterations: List[InformationCollectionIteration],
@@ -193,7 +243,7 @@ def construct_tool_chat_history(
             lambda iteration: list(iteration.codeContext.keys()) if iteration.codeContext else []
         ),
         ConversationCommand.Operator: (
-            lambda iteration: list(iteration.operatorContext.keys()) if iteration.operatorContext else []
+            lambda iteration: list(iteration.operatorContext.query) if iteration.operatorContext else []
         ),
     }
     for iteration in previous_iterations:
@@ -273,7 +323,7 @@ async def save_to_conversation_log(
     compiled_references: List[Dict[str, Any]] = [],
     online_results: Dict[str, Any] = {},
     code_results: Dict[str, Any] = {},
-    operator_results: Dict[str, str] = {},
+    operator_results: List[OperatorRun] = None,
     inferred_queries: List[str] = [],
     intent_type: str = "remember",
     client_application: ClientApplication = None,
@@ -301,8 +351,8 @@ async def save_to_conversation_log(
         "intent": {"inferred-queries": inferred_queries, "type": intent_type},
         "onlineContext": online_results,
         "codeContext": code_results,
-        "operatorContext": operator_results,
-        "researchContext": [vars(r) for r in research_results] if research_results and not chat_response else None,
+        "operatorContext": [o.to_dict() for o in operator_results] if operator_results and not chat_response else None,
+        "researchContext": [r.to_dict() for r in research_results] if research_results and not chat_response else None,
         "automationId": automation_id,
         "trainOfThought": train_of_thought,
         "turnId": turn_id,
@@ -459,10 +509,12 @@ def generate_chatml_messages_with_context(
             ]
 
         if not is_none_or_empty(chat.get("operatorContext")):
+            operator_context = chat.get("operatorContext")
+            operator_content = "\n\n".join([f'## Task: {oc["query"]}\n{oc["response"]}\n' for oc in operator_context])
             message_context += [
                 {
                     "type": "text",
-                    "text": f"{prompts.operator_execution_context.format(operator_results=chat.get('operatorContext'))}",
+                    "text": f"{prompts.operator_execution_context.format(operator_results=operator_content)}",
                 }
             ]
 
diff --git a/src/khoj/processor/operator/__init__.py b/src/khoj/processor/operator/__init__.py
index b2ea846f..e38ae777 100644
--- a/src/khoj/processor/operator/__init__.py
+++ b/src/khoj/processor/operator/__init__.py
@@ -6,6 +6,7 @@ from typing import Callable, List, Optional
 
 from khoj.database.adapters import AgentAdapters, ConversationAdapters
 from khoj.database.models import Agent, ChatModel, KhojUser
+from khoj.processor.conversation.utils import OperatorRun
 from khoj.processor.operator.operator_actions import *
 from khoj.processor.operator.operator_agent_anthropic import AnthropicOperatorAgent
 from khoj.processor.operator.operator_agent_base import OperatorAgent
@@ -160,11 +161,12 @@ async def operate_environment(
     if environment_type == EnvironmentType.BROWSER and hasattr(environment, "visited_urls"):
         webpages = [{"link": url, "snippet": ""} for url in environment.visited_urls]
 
-    yield {
-        "query": query,
-        "result": user_input_message or response,
-        "webpages": webpages,
-    }
+    yield OperatorRun(
+        query=query,
+        trajectory=operator_agent.messages,
+        response=response,
+        webpages=webpages,
+    )
 
 
 def is_operator_model(model: str) -> ChatModel.ModelType | None:
diff --git a/src/khoj/processor/operator/operator_agent_anthropic.py b/src/khoj/processor/operator/operator_agent_anthropic.py
index 567411f6..2b98d50d 100644
--- a/src/khoj/processor/operator/operator_agent_anthropic.py
+++ b/src/khoj/processor/operator/operator_agent_anthropic.py
@@ -10,12 +10,9 @@ from anthropic.types.beta import BetaContentBlock, BetaTextBlock, BetaToolUseBlo
 
 from khoj.database.models import ChatModel
 from khoj.processor.conversation.anthropic.utils import is_reasoning_model
+from khoj.processor.conversation.utils import AgentMessage
 from khoj.processor.operator.operator_actions import *
-from khoj.processor.operator.operator_agent_base import (
-    AgentActResult,
-    AgentMessage,
-    OperatorAgent,
-)
+from khoj.processor.operator.operator_agent_base import AgentActResult, OperatorAgent
 from khoj.processor.operator.operator_environment_base import (
     EnvironmentType,
     EnvState,
diff --git a/src/khoj/processor/operator/operator_agent_base.py b/src/khoj/processor/operator/operator_agent_base.py
index 8c273b5e..1aa0f238 100644
--- a/src/khoj/processor/operator/operator_agent_base.py
+++ b/src/khoj/processor/operator/operator_agent_base.py
@@ -5,7 +5,7 @@ from typing import List, Literal, Optional, Union
 from pydantic import BaseModel
 
 from khoj.database.models import ChatModel
-from khoj.processor.conversation.utils import commit_conversation_trace
+from khoj.processor.conversation.utils import AgentMessage, commit_conversation_trace
 from khoj.processor.operator.operator_actions import OperatorAction
 from khoj.processor.operator.operator_environment_base import (
     EnvironmentType,
@@ -23,11 +23,6 @@ class AgentActResult(BaseModel):
     rendered_response: Optional[dict] = None
 
 
-class AgentMessage(BaseModel):
-    role: Literal["user", "assistant", "system", "environment"]
-    content: Union[str, List]
-
-
 class OperatorAgent(ABC):
     def __init__(
         self, query: str, vision_model: ChatModel, environment_type: EnvironmentType, max_iterations: int, tracer: dict
diff --git a/src/khoj/processor/operator/operator_agent_binary.py b/src/khoj/processor/operator/operator_agent_binary.py
index b869e8bb..77e28442 100644
--- a/src/khoj/processor/operator/operator_agent_binary.py
+++ b/src/khoj/processor/operator/operator_agent_binary.py
@@ -5,15 +5,11 @@ from textwrap import dedent
 from typing import List
 
 from khoj.database.models import ChatModel
-from khoj.processor.conversation.utils import construct_structured_message
+from khoj.processor.conversation.utils import AgentMessage, construct_structured_message
 from khoj.processor.operator.grounding_agent import GroundingAgent
 from khoj.processor.operator.grounding_agent_uitars import GroundingAgentUitars
 from khoj.processor.operator.operator_actions import *
-from khoj.processor.operator.operator_agent_base import (
-    AgentActResult,
-    AgentMessage,
-    OperatorAgent,
-)
+from khoj.processor.operator.operator_agent_base import AgentActResult, OperatorAgent
 from khoj.processor.operator.operator_environment_base import (
     EnvironmentType,
     EnvState,
diff --git a/src/khoj/processor/operator/operator_agent_openai.py b/src/khoj/processor/operator/operator_agent_openai.py
index 2b665f4d..7ae71bff 100644
--- a/src/khoj/processor/operator/operator_agent_openai.py
+++ b/src/khoj/processor/operator/operator_agent_openai.py
@@ -8,12 +8,9 @@ from typing import List, Optional, cast
 
 from openai.types.responses import Response, ResponseOutputItem
 
+from khoj.processor.conversation.utils import AgentMessage
 from khoj.processor.operator.operator_actions import *
-from khoj.processor.operator.operator_agent_base import (
-    AgentActResult,
-    AgentMessage,
-    OperatorAgent,
-)
+from khoj.processor.operator.operator_agent_base import AgentActResult, OperatorAgent
 from khoj.processor.operator.operator_environment_base import (
     EnvironmentType,
     EnvState,
diff --git a/src/khoj/routers/api_chat.py b/src/khoj/routers/api_chat.py
index 39e8c1a1..2cade5bc 100644
--- a/src/khoj/routers/api_chat.py
+++ b/src/khoj/routers/api_chat.py
@@ -26,6 +26,7 @@ from khoj.database.models import Agent, KhojUser
 from khoj.processor.conversation import prompts
 from khoj.processor.conversation.prompts import help_message, no_entries_found
 from khoj.processor.conversation.utils import (
+    OperatorRun,
     ResponseWithThought,
     defilter_query,
     save_to_conversation_log,
@@ -725,7 +726,7 @@ async def chat(
         research_results: List[InformationCollectionIteration] = []
         online_results: Dict = dict()
         code_results: Dict = dict()
-        operator_results: Dict[str, str] = {}
+        operator_results: List[OperatorRun] = []
         compiled_references: List[Any] = []
         inferred_queries: List[Any] = []
         attached_file_context = gather_raw_query_files(query_files)
@@ -960,11 +961,12 @@ async def chat(
             last_message = conversation.messages[-1]
             online_results = {key: val.model_dump() for key, val in last_message.onlineContext.items() or []}
             code_results = {key: val.model_dump() for key, val in last_message.codeContext.items() or []}
-            operator_results = last_message.operatorContext or {}
             compiled_references = [ref.model_dump() for ref in last_message.context or []]
             research_results = [
                 InformationCollectionIteration(**iter_dict) for iter_dict in last_message.researchContext or []
             ]
+            operator_results = [OperatorRun(**iter_dict) for iter_dict in last_message.operatorContext or []]
+            train_of_thought = [thought.model_dump() for thought in last_message.trainOfThought or []]
             # Drop the interrupted message from conversation history
             meta_log["chat"].pop()
             logger.info(f"Loaded interrupted partial context from conversation {conversation_id}.")
@@ -1034,7 +1036,7 @@ async def chat(
                         if research_result.context:
                             compiled_references.extend(research_result.context)
                         if research_result.operatorContext:
-                            operator_results.update(research_result.operatorContext)
+                            operator_results.append(research_result.operatorContext)
                         research_results.append(research_result)
 
                 else:
@@ -1306,16 +1308,16 @@ async def chat(
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
                         yield result[ChatEvent.STATUS]
-                    else:
-                        operator_results = {result["query"]: result["result"]}
+                    elif isinstance(result, OperatorRun):
+                        operator_results.append(result)
                         # Add webpages visited while operating browser to references
-                        if result.get("webpages"):
+                        if result.webpages:
                             if not online_results.get(defiltered_query):
-                                online_results[defiltered_query] = {"webpages": result["webpages"]}
+                                online_results[defiltered_query] = {"webpages": result.webpages}
                             elif not online_results[defiltered_query].get("webpages"):
-                                online_results[defiltered_query]["webpages"] = result["webpages"]
+                                online_results[defiltered_query]["webpages"] = result.webpages
                             else:
-                                online_results[defiltered_query]["webpages"] += result["webpages"]
+                                online_results[defiltered_query]["webpages"] += result.webpages
             except ValueError as e:
                 program_execution_context.append(f"Browser operation error: {e}")
                 logger.warning(f"Failed to operate browser with {e}", exc_info=True)
@@ -1333,7 +1335,6 @@ async def chat(
                 "context": compiled_references,
                 "onlineContext": unique_online_results,
                 "codeContext": code_results,
-                "operatorContext": operator_results,
             },
         ):
             yield result
diff --git a/src/khoj/routers/helpers.py b/src/khoj/routers/helpers.py
index c1ddb82d..a3322b67 100644
--- a/src/khoj/routers/helpers.py
+++ b/src/khoj/routers/helpers.py
@@ -95,6 +95,7 @@ from khoj.processor.conversation.openai.gpt import (
 from khoj.processor.conversation.utils import (
     ChatEvent,
     InformationCollectionIteration,
+    OperatorRun,
     ResponseWithThought,
     clean_json,
     clean_mermaidjs,
@@ -1355,7 +1356,7 @@ async def agenerate_chat_response(
     compiled_references: List[Dict] = [],
     online_results: Dict[str, Dict] = {},
     code_results: Dict[str, Dict] = {},
-    operator_results: Dict[str, str] = {},
+    operator_results: List[OperatorRun] = [],
     research_results: List[InformationCollectionIteration] = [],
     inferred_queries: List[str] = [],
     conversation_commands: List[ConversationCommand] = [ConversationCommand.Default],
@@ -1414,7 +1415,7 @@ async def agenerate_chat_response(
             compiled_references = []
             online_results = {}
             code_results = {}
-            operator_results = {}
+            operator_results = []
             deepthought = True
 
         chat_model = await ConversationAdapters.aget_valid_chat_model(user, conversation, is_subscribed)
diff --git a/src/khoj/routers/research.py b/src/khoj/routers/research.py
index de55e47b..ab0c7062 100644
--- a/src/khoj/routers/research.py
+++ b/src/khoj/routers/research.py
@@ -14,6 +14,7 @@ from khoj.database.models import Agent, KhojUser
 from khoj.processor.conversation import prompts
 from khoj.processor.conversation.utils import (
     InformationCollectionIteration,
+    OperatorRun,
     construct_iteration_history,
     construct_tool_chat_history,
     load_complex_json,
@@ -248,7 +249,7 @@ async def execute_information_collection(
         online_results: Dict = dict()
         code_results: Dict = dict()
         document_results: List[Dict[str, str]] = []
-        operator_results: Dict[str, str] = {}
+        operator_results: OperatorRun = None
         summarize_files: str = ""
         this_iteration = InformationCollectionIteration(tool=None, query=query)
 
@@ -431,17 +432,17 @@ async def execute_information_collection(
                 ):
                     if isinstance(result, dict) and ChatEvent.STATUS in result:
                         yield result[ChatEvent.STATUS]
-                    else:
-                        operator_results = {result["query"]: result["result"]}
+                    elif isinstance(result, OperatorRun):
+                        operator_results = result
                         this_iteration.operatorContext = operator_results
                         # Add webpages visited while operating browser to references
-                        if result.get("webpages"):
+                        if result.webpages:
                             if not online_results.get(this_iteration.query):
-                                online_results[this_iteration.query] = {"webpages": result["webpages"]}
+                                online_results[this_iteration.query] = {"webpages": result.webpages}
                             elif not online_results[this_iteration.query].get("webpages"):
-                                online_results[this_iteration.query]["webpages"] = result["webpages"]
+                                online_results[this_iteration.query]["webpages"] = result.webpages
                             else:
-                                online_results[this_iteration.query]["webpages"] += result["webpages"]
+                                online_results[this_iteration.query]["webpages"] += result.webpages
                             this_iteration.onlineContext = online_results
             except Exception as e:
                 this_iteration.warning = f"Error operating browser: {e}"
@@ -489,7 +490,9 @@ async def execute_information_collection(
             if code_results:
                 results_data += f"\n<code_results>\n{yaml.dump(truncate_code_context(code_results), allow_unicode=True, sort_keys=False, default_flow_style=False)}\n</code_results>"
             if operator_results:
-                results_data += f"\n<browser_operator_results>\n{next(iter(operator_results.values()))}\n</browser_operator_results>"
+                results_data += (
+                    f"\n<browser_operator_results>\n{operator_results.response}\n</browser_operator_results>"
+                )
             if summarize_files:
                 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: