diff --git a/gateway/platforms/base.py b/gateway/platforms/base.py
index 1659c6524..918bc31bd 100644
--- a/gateway/platforms/base.py
+++ b/gateway/platforms/base.py
@@ -17,7 +17,8 @@ from typing import Dict, List, Optional, Any, Callable, Awaitable, Tuple
 from enum import Enum
 
 import sys
-sys.path.insert(0, str(__file__).rsplit("/", 3)[0])
+from pathlib import Path as _Path
+sys.path.insert(0, str(_Path(__file__).resolve().parents[2]))
 
 from gateway.config import Platform, PlatformConfig
 from gateway.session import SessionSource
diff --git a/gateway/platforms/discord.py b/gateway/platforms/discord.py
index f1c19bf17..5a1012dc1 100644
--- a/gateway/platforms/discord.py
+++ b/gateway/platforms/discord.py
@@ -27,7 +27,8 @@ except ImportError:
     commands = None
 
 import sys
-sys.path.insert(0, str(__file__).rsplit("/", 3)[0])
+from pathlib import Path as _Path
+sys.path.insert(0, str(_Path(__file__).resolve().parents[2]))
 
 from gateway.config import Platform, PlatformConfig
 from gateway.platforms.base import (
diff --git a/gateway/platforms/slack.py b/gateway/platforms/slack.py
index 865d57979..be5f5045b 100644
--- a/gateway/platforms/slack.py
+++ b/gateway/platforms/slack.py
@@ -24,7 +24,8 @@ except ImportError:
     AsyncWebClient = Any
 
 import sys
-sys.path.insert(0, str(__file__).rsplit("/", 3)[0])
+from pathlib import Path as _Path
+sys.path.insert(0, str(_Path(__file__).resolve().parents[2]))
 
 from gateway.config import Platform, PlatformConfig
 from gateway.platforms.base import (
diff --git a/gateway/platforms/telegram.py b/gateway/platforms/telegram.py
index db497b7bd..e0d277b7b 100644
--- a/gateway/platforms/telegram.py
+++ b/gateway/platforms/telegram.py
@@ -30,7 +30,8 @@ except ImportError:
     ContextTypes = Any
 
 import sys
-sys.path.insert(0, str(__file__).rsplit("/", 3)[0])
+from pathlib import Path as _Path
+sys.path.insert(0, str(_Path(__file__).resolve().parents[2]))
 
 from gateway.config import Platform, PlatformConfig
 from gateway.platforms.base import (
diff --git a/gateway/platforms/whatsapp.py b/gateway/platforms/whatsapp.py
index 71f0c33c5..a90f94e39 100644
--- a/gateway/platforms/whatsapp.py
+++ b/gateway/platforms/whatsapp.py
@@ -25,7 +25,7 @@ from typing import Dict, List, Optional, Any
 logger = logging.getLogger(__name__)
 
 import sys
-sys.path.insert(0, str(__file__).rsplit("/", 3)[0])
+sys.path.insert(0, str(Path(__file__).resolve().parents[2]))
 
 from gateway.config import Platform, PlatformConfig
 from gateway.platforms.base import (
diff --git a/run_agent.py b/run_agent.py
index 8c56512b4..b44360ab7 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -2284,7 +2284,337 @@ class AIAgent:
         self._cached_system_prompt = None
         if self._memory_store:
             self._memory_store.load_from_disk()
-    
+
+    def _build_api_kwargs(self, api_messages: list) -> dict:
+        """Build the keyword arguments dict for the chat completions API call."""
+        provider_preferences = {}
+        if self.providers_allowed:
+            provider_preferences["only"] = self.providers_allowed
+        if self.providers_ignored:
+            provider_preferences["ignore"] = self.providers_ignored
+        if self.providers_order:
+            provider_preferences["order"] = self.providers_order
+        if self.provider_sort:
+            provider_preferences["sort"] = self.provider_sort
+
+        api_kwargs = {
+            "model": self.model,
+            "messages": api_messages,
+            "tools": self.tools if self.tools else None,
+            "timeout": 600.0,
+        }
+
+        if self.max_tokens is not None:
+            api_kwargs["max_tokens"] = self.max_tokens
+
+        extra_body = {}
+
+        if provider_preferences:
+            extra_body["provider"] = provider_preferences
+
+        if "openrouter" in self.base_url.lower():
+            if self.reasoning_config is not None:
+                extra_body["reasoning"] = self.reasoning_config
+            else:
+                extra_body["reasoning"] = {
+                    "enabled": True,
+                    "effort": "xhigh"
+                }
+
+        if extra_body:
+            api_kwargs["extra_body"] = extra_body
+
+        return api_kwargs
+
+    def _build_assistant_message(self, assistant_message, finish_reason: str) -> dict:
+        """Build a normalized assistant message dict from an API response message.
+
+        Handles reasoning extraction, reasoning_details, and optional tool_calls
+        so both the tool-call path and the final-response path share one builder.
+        """
+        reasoning_text = self._extract_reasoning(assistant_message)
+
+        if reasoning_text and self.verbose_logging:
+            preview = reasoning_text[:100] + "..." if len(reasoning_text) > 100 else reasoning_text
+            logging.debug(f"Captured reasoning ({len(reasoning_text)} chars): {preview}")
+
+        msg = {
+            "role": "assistant",
+            "content": assistant_message.content or "",
+            "reasoning": reasoning_text,
+            "finish_reason": finish_reason,
+        }
+
+        if hasattr(assistant_message, 'reasoning_details') and assistant_message.reasoning_details:
+            msg["reasoning_details"] = [
+                {"type": d.get("type"), "text": d.get("text"), "signature": d.get("signature")}
+                for d in assistant_message.reasoning_details
+                if isinstance(d, dict)
+            ]
+
+        if assistant_message.tool_calls:
+            msg["tool_calls"] = [
+                {
+                    "id": tool_call.id,
+                    "type": tool_call.type,
+                    "function": {
+                        "name": tool_call.function.name,
+                        "arguments": tool_call.function.arguments
+                    }
+                }
+                for tool_call in assistant_message.tool_calls
+            ]
+
+        return msg
+
+    def _compress_context(self, messages: list, system_message: str, *, approx_tokens: int = None) -> tuple:
+        """Compress conversation context and split the session in SQLite.
+
+        Returns:
+            (compressed_messages, new_system_prompt) tuple
+        """
+        compressed = self.context_compressor.compress(messages, current_tokens=approx_tokens)
+
+        todo_snapshot = self._todo_store.format_for_injection()
+        if todo_snapshot:
+            compressed.append({"role": "user", "content": todo_snapshot})
+
+        self._invalidate_system_prompt()
+        new_system_prompt = self._build_system_prompt(system_message)
+        self._cached_system_prompt = new_system_prompt
+
+        if self._session_db:
+            try:
+                self._session_db.end_session(self.session_id, "compression")
+                old_session_id = self.session_id
+                self.session_id = f"{datetime.now().strftime('%Y%m%d_%H%M%S')}_{uuid.uuid4().hex[:6]}"
+                self._session_db.create_session(
+                    session_id=self.session_id,
+                    source=self.platform or "cli",
+                    model=self.model,
+                    parent_session_id=old_session_id,
+                )
+                self._session_db.update_system_prompt(self.session_id, new_system_prompt)
+            except Exception as e:
+                logger.debug("Session DB compression split failed: %s", e)
+
+        return compressed, new_system_prompt
+
+    def _execute_tool_calls(self, assistant_message, messages: list, effective_task_id: str) -> None:
+        """Execute tool calls from the assistant message and append results to messages."""
+        for i, tool_call in enumerate(assistant_message.tool_calls, 1):
+            function_name = tool_call.function.name
+
+            try:
+                function_args = json.loads(tool_call.function.arguments)
+            except json.JSONDecodeError as e:
+                logging.warning(f"Unexpected JSON error after validation: {e}")
+                function_args = {}
+
+            if not self.quiet_mode:
+                args_str = json.dumps(function_args, ensure_ascii=False)
+                args_preview = args_str[:self.log_prefix_chars] + "..." if len(args_str) > self.log_prefix_chars else args_str
+                print(f"  📞 Tool {i}: {function_name}({list(function_args.keys())}) - {args_preview}")
+
+            if self.tool_progress_callback:
+                try:
+                    preview = _build_tool_preview(function_name, function_args)
+                    self.tool_progress_callback(function_name, preview)
+                except Exception as cb_err:
+                    logging.debug(f"Tool progress callback error: {cb_err}")
+
+            tool_start_time = time.time()
+
+            if function_name == "todo":
+                from tools.todo_tool import todo_tool as _todo_tool
+                function_result = _todo_tool(
+                    todos=function_args.get("todos"),
+                    merge=function_args.get("merge", False),
+                    store=self._todo_store,
+                )
+                tool_duration = time.time() - tool_start_time
+                if self.quiet_mode:
+                    print(f"  {self._get_cute_tool_message('todo', function_args, tool_duration)}")
+            elif function_name == "session_search" and self._session_db:
+                from tools.session_search_tool import session_search as _session_search
+                function_result = _session_search(
+                    query=function_args.get("query", ""),
+                    role_filter=function_args.get("role_filter"),
+                    limit=function_args.get("limit", 3),
+                    db=self._session_db,
+                )
+                tool_duration = time.time() - tool_start_time
+                if self.quiet_mode:
+                    print(f"  {self._get_cute_tool_message('session_search', function_args, tool_duration)}")
+            elif function_name == "memory":
+                from tools.memory_tool import memory_tool as _memory_tool
+                function_result = _memory_tool(
+                    action=function_args.get("action"),
+                    target=function_args.get("target", "memory"),
+                    content=function_args.get("content"),
+                    old_text=function_args.get("old_text"),
+                    store=self._memory_store,
+                )
+                tool_duration = time.time() - tool_start_time
+                if self.quiet_mode:
+                    print(f"  {self._get_cute_tool_message('memory', function_args, tool_duration)}")
+            elif function_name == "clarify":
+                from tools.clarify_tool import clarify_tool as _clarify_tool
+                function_result = _clarify_tool(
+                    question=function_args.get("question", ""),
+                    choices=function_args.get("choices"),
+                    callback=self.clarify_callback,
+                )
+                tool_duration = time.time() - tool_start_time
+                if self.quiet_mode:
+                    print(f"  {self._get_cute_tool_message('clarify', function_args, tool_duration)}")
+            elif function_name == "delegate_task":
+                from tools.delegate_tool import delegate_task as _delegate_task
+                tasks_arg = function_args.get("tasks")
+                if tasks_arg and isinstance(tasks_arg, list):
+                    spinner_label = f"🔀 delegating {len(tasks_arg)} tasks"
+                else:
+                    goal_preview = (function_args.get("goal") or "")[:30]
+                    spinner_label = f"🔀 {goal_preview}" if goal_preview else "🔀 delegating"
+                spinner = None
+                if self.quiet_mode:
+                    face = random.choice(KawaiiSpinner.KAWAII_WAITING)
+                    spinner = KawaiiSpinner(f"{face} {spinner_label}", spinner_type='dots')
+                    spinner.start()
+                self._delegate_spinner = spinner
+                try:
+                    function_result = _delegate_task(
+                        goal=function_args.get("goal"),
+                        context=function_args.get("context"),
+                        toolsets=function_args.get("toolsets"),
+                        tasks=tasks_arg,
+                        model=function_args.get("model"),
+                        max_iterations=function_args.get("max_iterations"),
+                        parent_agent=self,
+                    )
+                finally:
+                    self._delegate_spinner = None
+                    tool_duration = time.time() - tool_start_time
+                    cute_msg = self._get_cute_tool_message('delegate_task', function_args, tool_duration)
+                    if spinner:
+                        spinner.stop(cute_msg)
+                    elif self.quiet_mode:
+                        print(f"  {cute_msg}")
+            elif self.quiet_mode:
+                face = random.choice(KawaiiSpinner.KAWAII_WAITING)
+                tool_emoji_map = {
+                    'web_search': '🔍', 'web_extract': '📄', 'web_crawl': '🕸️',
+                    'terminal': '💻', 'process': '⚙️',
+                    'read_file': '📖', 'write_file': '✍️', 'patch': '🔧', 'search_files': '🔎',
+                    'browser_navigate': '🌐', 'browser_snapshot': '📸',
+                    'browser_click': '👆', 'browser_type': '⌨️',
+                    'browser_scroll': '📜', 'browser_back': '◀️',
+                    'browser_press': '⌨️', 'browser_close': '🚪',
+                    'browser_get_images': '🖼️', 'browser_vision': '👁️',
+                    'image_generate': '🎨', 'text_to_speech': '🔊',
+                    'vision_analyze': '👁️', 'mixture_of_agents': '🧠',
+                    'skills_list': '📚', 'skill_view': '📚',
+                    'schedule_cronjob': '⏰', 'list_cronjobs': '⏰', 'remove_cronjob': '⏰',
+                    'send_message': '📨', 'todo': '📋', 'memory': '🧠', 'session_search': '🔍',
+                    'clarify': '❓', 'execute_code': '🐍', 'delegate_task': '🔀',
+                }
+                emoji = tool_emoji_map.get(function_name, '⚡')
+                preview = _build_tool_preview(function_name, function_args) or function_name
+                if len(preview) > 30:
+                    preview = preview[:27] + "..."
+                spinner = KawaiiSpinner(f"{face} {emoji} {preview}", spinner_type='dots')
+                spinner.start()
+                try:
+                    function_result = handle_function_call(function_name, function_args, effective_task_id)
+                finally:
+                    tool_duration = time.time() - tool_start_time
+                    cute_msg = self._get_cute_tool_message(function_name, function_args, tool_duration)
+                    spinner.stop(cute_msg)
+            else:
+                function_result = handle_function_call(function_name, function_args, effective_task_id)
+                tool_duration = time.time() - tool_start_time
+
+            result_preview = function_result[:200] if len(function_result) > 200 else function_result
+
+            if self.verbose_logging:
+                logging.debug(f"Tool {function_name} completed in {tool_duration:.2f}s")
+                logging.debug(f"Tool result preview: {result_preview}...")
+
+            messages.append({
+                "role": "tool",
+                "content": function_result,
+                "tool_call_id": tool_call.id
+            })
+
+            if not self.quiet_mode:
+                response_preview = function_result[:self.log_prefix_chars] + "..." if len(function_result) > self.log_prefix_chars else function_result
+                print(f"  ✅ Tool {i} completed in {tool_duration:.2f}s - {response_preview}")
+
+            if self._interrupt_requested and i < len(assistant_message.tool_calls):
+                remaining = len(assistant_message.tool_calls) - i
+                print(f"{self.log_prefix}⚡ Interrupt: skipping {remaining} remaining tool call(s)")
+                for skipped_tc in assistant_message.tool_calls[i:]:
+                    messages.append({
+                        "role": "tool",
+                        "content": "[Tool execution skipped - user sent a new message]",
+                        "tool_call_id": skipped_tc.id
+                    })
+                break
+
+            if self.tool_delay > 0 and i < len(assistant_message.tool_calls):
+                time.sleep(self.tool_delay)
+
+    def _handle_max_iterations(self, messages: list, api_call_count: int) -> str:
+        """Request a summary when max iterations are reached. Returns the final response text."""
+        print(f"⚠️  Reached maximum iterations ({self.max_iterations}). Requesting summary...")
+
+        summary_request = (
+            "You've reached the maximum number of tool-calling iterations allowed. "
+            "Please provide a final response summarizing what you've found and accomplished so far, "
+            "without calling any more tools."
+        )
+        messages.append({"role": "user", "content": summary_request})
+
+        try:
+            api_messages = messages.copy()
+            if self.ephemeral_system_prompt:
+                api_messages = [{"role": "system", "content": self.ephemeral_system_prompt}] + api_messages
+
+            summary_extra_body = {}
+            if "openrouter" in self.base_url.lower():
+                if self.reasoning_config is not None:
+                    summary_extra_body["reasoning"] = self.reasoning_config
+                else:
+                    summary_extra_body["reasoning"] = {
+                        "enabled": True,
+                        "effort": "xhigh"
+                    }
+
+            summary_kwargs = {
+                "model": self.model,
+                "messages": api_messages,
+            }
+            if self.max_tokens is not None:
+                summary_kwargs["max_tokens"] = self.max_tokens
+            if summary_extra_body:
+                summary_kwargs["extra_body"] = summary_extra_body
+
+            summary_response = self.client.chat.completions.create(**summary_kwargs)
+
+            if summary_response.choices and summary_response.choices[0].message.content:
+                final_response = summary_response.choices[0].message.content
+                if "<think>" in final_response:
+                    final_response = re.sub(r'<think>.*?</think>\s*', '', final_response, flags=re.DOTALL).strip()
+                messages.append({"role": "assistant", "content": final_response})
+            else:
+                final_response = "I reached the iteration limit and couldn't generate a summary."
+
+        except Exception as e:
+            logging.warning(f"Failed to get summary response: {e}")
+            final_response = f"I reached the maximum iterations ({self.max_iterations}) but couldn't summarize. Error: {str(e)}"
+
+        return final_response
+
     def run_conversation(
         self,
         user_message: str,
@@ -2443,50 +2773,7 @@ class AIAgent:
 
             while retry_count <= max_retries:
                 try:
-                    # Build OpenRouter provider preferences if specified
-                    provider_preferences = {}
-                    if self.providers_allowed:
-                        provider_preferences["only"] = self.providers_allowed
-                    if self.providers_ignored:
-                        provider_preferences["ignore"] = self.providers_ignored
-                    if self.providers_order:
-                        provider_preferences["order"] = self.providers_order
-                    if self.provider_sort:
-                        provider_preferences["sort"] = self.provider_sort
-                    
-                    # Make API call with tools - increased timeout for long responses
-                    api_kwargs = {
-                        "model": self.model,
-                        "messages": api_messages,
-                        "tools": self.tools if self.tools else None,
-                        "timeout": 600.0  # 10 minute timeout for very long responses
-                    }
-                    
-                    # Add max_tokens if configured (overrides model default)
-                    if self.max_tokens is not None:
-                        api_kwargs["max_tokens"] = self.max_tokens
-                    
-                    # Add extra_body for OpenRouter (provider preferences + reasoning)
-                    extra_body = {}
-                    
-                    # Add provider preferences if specified
-                    if provider_preferences:
-                        extra_body["provider"] = provider_preferences
-                    
-                    # Configure reasoning for OpenRouter
-                    # If reasoning_config is explicitly provided, use it (allows disabling/customizing)
-                    # Otherwise, default to xhigh effort for OpenRouter models
-                    if "openrouter" in self.base_url.lower():
-                        if self.reasoning_config is not None:
-                            extra_body["reasoning"] = self.reasoning_config
-                        else:
-                            extra_body["reasoning"] = {
-                                "enabled": True,
-                                "effort": "xhigh"
-                            }
-                    
-                    if extra_body:
-                        api_kwargs["extra_body"] = extra_body
+                    api_kwargs = self._build_api_kwargs(api_messages)
 
                     if os.getenv("HERMES_DUMP_REQUESTS", "").strip().lower() in {"1", "true", "yes", "on"}:
                         self._dump_api_request_debug(api_kwargs, reason="preflight")
@@ -2717,34 +3004,12 @@ class AIAgent:
                     if is_context_length_error:
                         print(f"{self.log_prefix}⚠️  Context length exceeded - attempting compression...")
                         
-                        # Try to compress and retry
                         original_len = len(messages)
-                        messages = self.context_compressor.compress(messages, current_tokens=approx_tokens)
+                        messages, active_system_prompt = self._compress_context(
+                            messages, system_message, approx_tokens=approx_tokens
+                        )
                         
                         if len(messages) < original_len:
-                            # Compression was possible -- re-inject todo state
-                            todo_snapshot = self._todo_store.format_for_injection()
-                            if todo_snapshot:
-                                messages.append({"role": "user", "content": todo_snapshot})
-                            # Rebuild system prompt with fresh date/time + memory
-                            self._invalidate_system_prompt()
-                            active_system_prompt = self._build_system_prompt(system_message)
-                            self._cached_system_prompt = active_system_prompt
-                            # Split session in SQLite (close old, open new with parent link)
-                            if self._session_db:
-                                try:
-                                    self._session_db.end_session(self.session_id, "compression")
-                                    old_session_id = self.session_id
-                                    self.session_id = f"{datetime.now().strftime('%Y%m%d_%H%M%S')}_{uuid.uuid4().hex[:6]}"
-                                    self._session_db.create_session(
-                                        session_id=self.session_id,
-                                        source=self.platform or "cli",
-                                        model=self.model,
-                                        parent_session_id=old_session_id,
-                                    )
-                                    self._session_db.update_system_prompt(self.session_id, active_system_prompt)
-                                except Exception as e:
-                                    logger.debug("Session DB compression split failed: %s", e)
                             print(f"{self.log_prefix}   🗜️  Compressed {original_len} → {len(messages)} messages, retrying...")
                             continue  # Retry with compressed messages
                         else:
@@ -2921,262 +3186,17 @@ class AIAgent:
                     # Reset retry counter on successful JSON validation
                     self._invalid_json_retries = 0
                     
-                    # Extract reasoning from response if available
-                    # OpenRouter can return reasoning in multiple formats:
-                    # 1. message.reasoning - direct reasoning field
-                    # 2. message.reasoning_content - alternative field (some providers)
-                    # 3. message.reasoning_details - array with {summary: "..."} objects
-                    reasoning_text = self._extract_reasoning(assistant_message)
-                    
-                    if reasoning_text and self.verbose_logging:
-                        preview = reasoning_text[:100] + "..." if len(reasoning_text) > 100 else reasoning_text
-                        logging.debug(f"Captured reasoning ({len(reasoning_text)} chars): {preview}")
-                    
-                    # Build assistant message with tool calls
-                    # Content stays as-is; reasoning is stored separately and will be passed
-                    # to the API via reasoning_content field when preparing api_messages
-                    assistant_msg = {
-                        "role": "assistant",
-                        "content": assistant_message.content or "",
-                        "reasoning": reasoning_text,
-                        "finish_reason": finish_reason,
-                        "tool_calls": [
-                            {
-                                "id": tool_call.id,
-                                "type": tool_call.type,
-                                "function": {
-                                    "name": tool_call.function.name,
-                                    "arguments": tool_call.function.arguments
-                                }
-                            }
-                            for tool_call in assistant_message.tool_calls
-                        ]
-                    }
-                    
-                    # Store reasoning_details for multi-turn reasoning context (OpenRouter)
-                    if hasattr(assistant_message, 'reasoning_details') and assistant_message.reasoning_details:
-                        assistant_msg["reasoning_details"] = [
-                            {"type": d.get("type"), "text": d.get("text"), "signature": d.get("signature")}
-                            for d in assistant_message.reasoning_details
-                            if isinstance(d, dict)
-                        ]
+                    assistant_msg = self._build_assistant_message(assistant_message, finish_reason)
                     
                     messages.append(assistant_msg)
                     
-                    # Execute each tool call
-                    for i, tool_call in enumerate(assistant_message.tool_calls, 1):
-                        function_name = tool_call.function.name
-                        
-                        # Parse arguments - should always succeed since we validated above
-                        try:
-                            function_args = json.loads(tool_call.function.arguments)
-                        except json.JSONDecodeError as e:
-                            # This shouldn't happen since we validate and retry above
-                            logging.warning(f"Unexpected JSON error after validation: {e}")
-                            function_args = {}
-                        
-                        # Preview tool call - cleaner format for quiet mode
-                        if not self.quiet_mode:
-                            args_str = json.dumps(function_args, ensure_ascii=False)
-                            args_preview = args_str[:self.log_prefix_chars] + "..." if len(args_str) > self.log_prefix_chars else args_str
-                            print(f"  📞 Tool {i}: {function_name}({list(function_args.keys())}) - {args_preview}")
-                        
-                        # Fire progress callback if registered (for messaging platforms)
-                        if self.tool_progress_callback:
-                            try:
-                                # Build a short preview of the primary argument
-                                preview = _build_tool_preview(function_name, function_args)
-                                self.tool_progress_callback(function_name, preview)
-                            except Exception as cb_err:
-                                logging.debug(f"Tool progress callback error: {cb_err}")
-
-                        tool_start_time = time.time()
-
-                        # Todo tool -- handle directly (needs agent's TodoStore instance)
-                        if function_name == "todo":
-                            from tools.todo_tool import todo_tool as _todo_tool
-                            function_result = _todo_tool(
-                                todos=function_args.get("todos"),
-                                merge=function_args.get("merge", False),
-                                store=self._todo_store,
-                            )
-                            tool_duration = time.time() - tool_start_time
-                            if self.quiet_mode:
-                                print(f"  {self._get_cute_tool_message('todo', function_args, tool_duration)}")
-                        # Session search -- handle directly (needs SessionDB instance)
-                        elif function_name == "session_search" and self._session_db:
-                            from tools.session_search_tool import session_search as _session_search
-                            function_result = _session_search(
-                                query=function_args.get("query", ""),
-                                role_filter=function_args.get("role_filter"),
-                                limit=function_args.get("limit", 3),
-                                db=self._session_db,
-                            )
-                            tool_duration = time.time() - tool_start_time
-                            if self.quiet_mode:
-                                print(f"  {self._get_cute_tool_message('session_search', function_args, tool_duration)}")
-                        # Memory tool -- handle directly (needs agent's MemoryStore instance)
-                        elif function_name == "memory":
-                            from tools.memory_tool import memory_tool as _memory_tool
-                            function_result = _memory_tool(
-                                action=function_args.get("action"),
-                                target=function_args.get("target", "memory"),
-                                content=function_args.get("content"),
-                                old_text=function_args.get("old_text"),
-                                store=self._memory_store,
-                            )
-                            tool_duration = time.time() - tool_start_time
-                            if self.quiet_mode:
-                                print(f"  {self._get_cute_tool_message('memory', function_args, tool_duration)}")
-                        # Clarify tool -- delegates to platform-provided callback
-                        elif function_name == "clarify":
-                            from tools.clarify_tool import clarify_tool as _clarify_tool
-                            function_result = _clarify_tool(
-                                question=function_args.get("question", ""),
-                                choices=function_args.get("choices"),
-                                callback=self.clarify_callback,
-                            )
-                            tool_duration = time.time() - tool_start_time
-                            if self.quiet_mode:
-                                print(f"  {self._get_cute_tool_message('clarify', function_args, tool_duration)}")
-                        # Delegate task -- spawn child agent(s) with isolated context
-                        elif function_name == "delegate_task":
-                            from tools.delegate_tool import delegate_task as _delegate_task
-                            tasks_arg = function_args.get("tasks")
-                            if tasks_arg and isinstance(tasks_arg, list):
-                                spinner_label = f"🔀 delegating {len(tasks_arg)} tasks"
-                            else:
-                                goal_preview = (function_args.get("goal") or "")[:30]
-                                spinner_label = f"🔀 {goal_preview}" if goal_preview else "🔀 delegating"
-                            spinner = None
-                            if self.quiet_mode:
-                                face = random.choice(KawaiiSpinner.KAWAII_WAITING)
-                                spinner = KawaiiSpinner(f"{face} {spinner_label}", spinner_type='dots')
-                                spinner.start()
-                            # Store spinner on self so delegate_tool can update its text
-                            self._delegate_spinner = spinner
-                            try:
-                                function_result = _delegate_task(
-                                    goal=function_args.get("goal"),
-                                    context=function_args.get("context"),
-                                    toolsets=function_args.get("toolsets"),
-                                    tasks=tasks_arg,
-                                    model=function_args.get("model"),
-                                    max_iterations=function_args.get("max_iterations"),
-                                    parent_agent=self,
-                                )
-                            finally:
-                                self._delegate_spinner = None
-                                tool_duration = time.time() - tool_start_time
-                                cute_msg = self._get_cute_tool_message('delegate_task', function_args, tool_duration)
-                                if spinner:
-                                    spinner.stop(cute_msg)
-                                elif self.quiet_mode:
-                                    print(f"  {cute_msg}")
-                        # Execute other tools - with animated kawaii spinner in quiet mode
-                        # The face is "alive" while the tool works, then vanishes
-                        # and is replaced by the clean result line.
-                        elif self.quiet_mode:
-                            face = random.choice(KawaiiSpinner.KAWAII_WAITING)
-                            tool_emoji_map = {
-                                'web_search': '🔍', 'web_extract': '📄', 'web_crawl': '🕸️',
-                                'terminal': '💻', 'process': '⚙️',
-                                'read_file': '📖', 'write_file': '✍️', 'patch': '🔧', 'search_files': '🔎',
-                                'browser_navigate': '🌐', 'browser_snapshot': '📸',
-                                'browser_click': '👆', 'browser_type': '⌨️',
-                                'browser_scroll': '📜', 'browser_back': '◀️',
-                                'browser_press': '⌨️', 'browser_close': '🚪',
-                                'browser_get_images': '🖼️', 'browser_vision': '👁️',
-                                'image_generate': '🎨', 'text_to_speech': '🔊',
-                                'vision_analyze': '👁️', 'mixture_of_agents': '🧠',
-                                'skills_list': '📚', 'skill_view': '📚',
-                                'schedule_cronjob': '⏰', 'list_cronjobs': '⏰', 'remove_cronjob': '⏰',
-                                'send_message': '📨', 'todo': '📋', 'memory': '🧠', 'session_search': '🔍',
-                                'clarify': '❓', 'execute_code': '🐍', 'delegate_task': '🔀',
-                            }
-                            emoji = tool_emoji_map.get(function_name, '⚡')
-                            preview = _build_tool_preview(function_name, function_args) or function_name
-                            if len(preview) > 30:
-                                preview = preview[:27] + "..."
-                            spinner = KawaiiSpinner(f"{face} {emoji} {preview}", spinner_type='dots')
-                            spinner.start()
-                            try:
-                                function_result = handle_function_call(function_name, function_args, effective_task_id)
-                            finally:
-                                tool_duration = time.time() - tool_start_time
-                                cute_msg = self._get_cute_tool_message(function_name, function_args, tool_duration)
-                                spinner.stop(cute_msg)
-                        else:
-                            function_result = handle_function_call(function_name, function_args, effective_task_id)
-                            tool_duration = time.time() - tool_start_time
-
-                        result_preview = function_result[:200] if len(function_result) > 200 else function_result
-
-                        if self.verbose_logging:
-                            logging.debug(f"Tool {function_name} completed in {tool_duration:.2f}s")
-                            logging.debug(f"Tool result preview: {result_preview}...")
-
-                        # Add tool result to conversation
-                        messages.append({
-                            "role": "tool",
-                            "content": function_result,
-                            "tool_call_id": tool_call.id
-                        })
-
-                        # Preview tool response (only in non-quiet mode)
-                        if not self.quiet_mode:
-                            response_preview = function_result[:self.log_prefix_chars] + "..." if len(function_result) > self.log_prefix_chars else function_result
-                            print(f"  ✅ Tool {i} completed in {tool_duration:.2f}s - {response_preview}")
-                        
-                        # Check for interrupt between tool calls - skip remaining
-                        # tools so the agent can respond to the user immediately
-                        if self._interrupt_requested and i < len(assistant_message.tool_calls):
-                            remaining = len(assistant_message.tool_calls) - i
-                            print(f"{self.log_prefix}⚡ Interrupt: skipping {remaining} remaining tool call(s)")
-                            # Add placeholder results for skipped tool calls so the
-                            # message sequence stays valid (assistant tool_calls need matching tool results)
-                            for skipped_tc in assistant_message.tool_calls[i:]:
-                                messages.append({
-                                    "role": "tool",
-                                    "content": "[Tool execution skipped - user sent a new message]",
-                                    "tool_call_id": skipped_tc.id
-                                })
-                            break
-                        
-                        # Delay between tool calls
-                        if self.tool_delay > 0 and i < len(assistant_message.tool_calls):
-                            time.sleep(self.tool_delay)
+                    self._execute_tool_calls(assistant_message, messages, effective_task_id)
                     
-                    # Check if context compression is needed before next API call
-                    # Uses actual token count from last API response
                     if self.compression_enabled and self.context_compressor.should_compress():
-                        messages = self.context_compressor.compress(
-                            messages, 
-                            current_tokens=self.context_compressor.last_prompt_tokens
+                        messages, active_system_prompt = self._compress_context(
+                            messages, system_message,
+                            approx_tokens=self.context_compressor.last_prompt_tokens
                         )
-                        # Re-inject todo state after compression
-                        todo_snapshot = self._todo_store.format_for_injection()
-                        if todo_snapshot:
-                            messages.append({"role": "user", "content": todo_snapshot})
-                        # Rebuild system prompt with fresh date/time + memory
-                        self._invalidate_system_prompt()
-                        active_system_prompt = self._build_system_prompt(system_message)
-                        self._cached_system_prompt = active_system_prompt
-                        # Split session in SQLite (close old, open new with parent link)
-                        if self._session_db:
-                            try:
-                                self._session_db.end_session(self.session_id, "compression")
-                                old_session_id = self.session_id
-                                self.session_id = f"{datetime.now().strftime('%Y%m%d_%H%M%S')}_{uuid.uuid4().hex[:6]}"
-                                self._session_db.create_session(
-                                    session_id=self.session_id,
-                                    source=self.platform or "cli",
-                                    model=self.model,
-                                    parent_session_id=old_session_id,
-                                )
-                                self._session_db.update_system_prompt(self.session_id, active_system_prompt)
-                            except Exception as e:
-                                logger.debug("Session DB compression split failed: %s", e)
                     
                     # Save session log incrementally (so progress is visible even if interrupted)
                     self._session_messages = messages
@@ -3242,28 +3262,7 @@ class AIAgent:
                     if hasattr(self, '_empty_content_retries'):
                         self._empty_content_retries = 0
                     
-                    # Extract reasoning from response if available
-                    reasoning_text = self._extract_reasoning(assistant_message)
-                    
-                    if reasoning_text and self.verbose_logging:
-                        preview = reasoning_text[:100] + "..." if len(reasoning_text) > 100 else reasoning_text
-                        logging.debug(f"Captured final reasoning ({len(reasoning_text)} chars): {preview}")
-                    
-                    # Build final assistant message
-                    final_msg = {
-                        "role": "assistant", 
-                        "content": final_response,
-                        "reasoning": reasoning_text,
-                        "finish_reason": finish_reason,
-                    }
-                    
-                    # Store reasoning_details for multi-turn reasoning context (OpenRouter)
-                    if hasattr(assistant_message, 'reasoning_details') and assistant_message.reasoning_details:
-                        final_msg["reasoning_details"] = [
-                            {"type": d.get("type"), "text": d.get("text"), "signature": d.get("signature")}
-                            for d in assistant_message.reasoning_details
-                            if isinstance(d, dict)
-                        ]
+                    final_msg = self._build_assistant_message(assistant_message, finish_reason)
                     
                     messages.append(final_msg)
                     
@@ -3289,61 +3288,8 @@ class AIAgent:
                     final_response = f"I apologize, but I encountered repeated errors: {error_msg}"
                     break
         
-        # Handle max iterations reached - ask model to summarize what it found
         if api_call_count >= self.max_iterations and final_response is None:
-            print(f"⚠️  Reached maximum iterations ({self.max_iterations}). Requesting summary...")
-            
-            # Inject a user message asking for a summary
-            summary_request = (
-                "You've reached the maximum number of tool-calling iterations allowed. "
-                "Please provide a final response summarizing what you've found and accomplished so far, "
-                "without calling any more tools."
-            )
-            messages.append({"role": "user", "content": summary_request})
-            
-            # Make one final API call WITHOUT tools to force a text response
-            try:
-                api_messages = messages.copy()
-                if self.ephemeral_system_prompt:
-                    api_messages = [{"role": "system", "content": self.ephemeral_system_prompt}] + api_messages
-                
-                # Build extra_body for summary call (same reasoning config as main loop)
-                summary_extra_body = {}
-                if "openrouter" in self.base_url.lower():
-                    if self.reasoning_config is not None:
-                        summary_extra_body["reasoning"] = self.reasoning_config
-                    else:
-                        summary_extra_body["reasoning"] = {
-                            "enabled": True,
-                            "effort": "xhigh"
-                        }
-                
-                summary_kwargs = {
-                    "model": self.model,
-                    "messages": api_messages,
-                    # No tools parameter - forces text response
-                }
-                if self.max_tokens is not None:
-                    summary_kwargs["max_tokens"] = self.max_tokens
-                if summary_extra_body:
-                    summary_kwargs["extra_body"] = summary_extra_body
-                
-                summary_response = self.client.chat.completions.create(**summary_kwargs)
-                
-                if summary_response.choices and summary_response.choices[0].message.content:
-                    final_response = summary_response.choices[0].message.content
-                    # Strip think blocks from final response
-                    if "<think>" in final_response:
-                        final_response = re.sub(r'<think>.*?</think>\s*', '', final_response, flags=re.DOTALL).strip()
-                    
-                    # Add to messages for session continuity
-                    messages.append({"role": "assistant", "content": final_response})
-                else:
-                    final_response = "I reached the iteration limit and couldn't generate a summary."
-                    
-            except Exception as e:
-                logging.warning(f"Failed to get summary response: {e}")
-                final_response = f"I reached the maximum iterations ({self.max_iterations}) but couldn't summarize. Error: {str(e)}"
+            final_response = self._handle_max_iterations(messages, api_call_count)
         
         # Determine if conversation completed successfully
         completed = final_response is not None and api_call_count < self.max_iterations