release: version 0.9.16 🚀

Containerfile

@@ -12,7 +12,10 @@ WORKDIR /app
 
 # Install system dependencies
 RUN apt-get update && apt-get install -y --no-install-recommends \
+    ca-certificates \
     curl \
+    git \
+    && update-ca-certificates \
     && rm -rf /var/lib/apt/lists/*
 
 # Install dependencies

HISTORY.md

@@ -5,10 +5,111 @@ Changelog
 (unreleased)
 ------------
 
+Fix
+~~~
+- Better LLM failure tracing, refs NOISSUE. [Simon Diesenreiter]
+
+
+0.9.15 (2026-04-11)
+-------------------
+
+Fix
+~~~
+- Increase LLM timeouts, refs NOISSUE. [Simon Diesenreiter]
+
+Other
+~~~~~
+
+
+0.9.14 (2026-04-11)
+-------------------
+
+Fix
+~~~
+- Add Ollama connection health details in UI, refs NOISSUE. [Simon
+  Diesenreiter]
+
+Other
+~~~~~
+
+
+0.9.13 (2026-04-11)
+-------------------
+
+Fix
+~~~
+- Fix internal server error, refs NOISSUE. [Simon Diesenreiter]
+
+Other
+~~~~~
+
+
+0.9.12 (2026-04-11)
+-------------------
+
+Fix
+~~~
+- Remove heuristic decision making fallbacks, refs NOISSUE. [Simon
+  Diesenreiter]
+
+Other
+~~~~~
+
+
+0.9.11 (2026-04-11)
+-------------------
+
+Fix
+~~~
+- Project association improvements, refs NOISSUE. [Simon Diesenreiter]
+
+Other
+~~~~~
+
+
+0.9.10 (2026-04-11)
+-------------------
+
+Fix
+~~~
+- More git integration fixes, refs NOISSUE. [Simon Diesenreiter]
+
+Other
+~~~~~
+
+
+0.9.9 (2026-04-11)
+------------------
+
+Fix
+~~~
+- Add missing git binary, refs NOISSUE. [Simon Diesenreiter]
+
+Other
+~~~~~
+
+
+0.9.8 (2026-04-11)
+------------------
+
+Fix
+~~~
+- More file change fixes, refs NOISSUE. [Simon Diesenreiter]
+
+Other
+~~~~~
+
+
+0.9.7 (2026-04-11)
+------------------
+
 Fix
 ~~~
 - More file generation improvements, refs NOISSUE. [Simon Diesenreiter]
 
+Other
+~~~~~
+
 
 0.9.6 (2026-04-11)
 ------------------

ai_software_factory/VERSION

@@ -1 +1 @@
-0.9.7
+0.9.16

ai_software_factory/agents/database_manager.py

@@ -2272,6 +2272,7 @@ class DatabaseManager:
                 "timeline": [],
                 "issues": [],
                 "issue_work": [],
+                "ui_data": {},
             }
         
         # Get logs
@@ -2296,6 +2297,7 @@ class DatabaseManager:
         llm_traces = self.get_llm_traces(project_id=project_id)
         correlations = self.get_prompt_change_correlations(project_id=project_id)
         code_changes, local_only_code_changes, orphan_code_changes = self._partition_code_changes(raw_code_changes, commits)
+        ui_data = self._get_latest_ui_snapshot_data(history.id)
         repository = self._get_project_repository(history)
         timeline = self.get_project_timeline(project_id=project_id)
         repository_sync = self.get_repository_sync_status(project_id=project_id)
@@ -2306,6 +2308,10 @@ class DatabaseManager:
             if commit.get('remote_status') == 'pushed' or commit.get('imported_from_remote') or commit.get('commit_url')
         ]
         has_pull_request = any(pr.get('pr_state') == 'open' and not pr.get('merged') for pr in pull_requests)
+        published_non_main_commits = [
+            commit for commit in published_commits
+            if (commit.get('branch') or '').strip() not in {'', 'main', 'master'}
+        ]
         if orphan_code_changes:
             delivery_status = 'uncommitted'
             delivery_message = (
@@ -2318,12 +2324,15 @@ class DatabaseManager:
                 f"{len(local_only_code_changes)} generated file change(s) were committed only in the local workspace. "
                 "No remote repo push was recorded for this prompt yet."
             )
-        elif published_commits and repository and repository.get('mode') == 'project' and not has_pull_request:
+        elif published_non_main_commits and repository and repository.get('mode') == 'project' and not has_pull_request:
             delivery_status = 'pushed_no_pr'
             delivery_message = 'Changes were pushed to the remote repository, but no pull request is currently tracked for review.'
         elif published_commits:
             delivery_status = 'delivered'
-            delivery_message = 'Generated changes were published to the tracked repository and are reviewable through the recorded pull request.'
+            if has_pull_request:
+                delivery_message = 'Generated changes were published to the tracked repository and are reviewable through the recorded pull request.'
+            else:
+                delivery_message = 'Generated changes were published directly to the tracked repository default branch.'
         else:
             delivery_status = 'pending'
             delivery_message = 'No git commit has been recorded for this project yet.'
@@ -2395,6 +2404,7 @@ class DatabaseManager:
             "repository_sync": repository_sync,
             "issues": issues,
             "issue_work": issue_work,
+            "ui_data": ui_data,
         }
 
     def get_prompt_events(self, project_id: str | None = None, limit: int = 100) -> list[dict]:
@@ -2493,6 +2503,7 @@ class DatabaseManager:
         archived_project_bundles = [self.get_project_audit_data(project.project_id) for project in archived_projects[:limit]]
         all_project_bundles = [self.get_project_audit_data(project.project_id) for project in active_projects]
         all_project_bundles.extend(self.get_project_audit_data(project.project_id) for project in archived_projects)
+        recent_llm_traces = self.get_llm_traces(limit=limit * 20)
         system_logs = self.db.query(SystemLog).order_by(SystemLog.created_at.desc()).limit(limit).all()
         return {
             "summary": {
@@ -2522,6 +2533,7 @@ class DatabaseManager:
                 }
                 for log in system_logs
             ],
+            "recent_llm_traces": recent_llm_traces,
             "lineage_links": self.get_prompt_change_links(limit=limit * 10),
             "correlations": self.get_prompt_change_correlations(limit=limit),
             "prompt_queue": {

ai_software_factory/agents/gitea.py

@@ -58,6 +58,18 @@ class GiteaAPI:
         """Build a Gitea API URL from a relative path."""
         return f"{self.base_url}/api/v1/{path.lstrip('/')}"
 
+    def _normalize_pull_request_head(self, head: str | None, owner: str | None = None) -> str | None:
+        """Return a Gitea-compatible head ref for pull request creation."""
+        normalized = (head or '').strip()
+        if not normalized:
+            return None
+        if ':' in normalized:
+            return normalized
+        effective_owner = (owner or self.owner or '').strip()
+        if not effective_owner:
+            return normalized
+        return f"{effective_owner}:{normalized}"
+
     def build_repo_git_url(self, owner: str | None = None, repo: str | None = None) -> str | None:
         """Build the clone URL for a repository."""
         _owner = owner or self.owner
@@ -222,11 +234,12 @@ class GiteaAPI:
         """Create a pull request."""
         _owner = owner or self.owner
         _repo = repo or self.repo
+        normalized_head = self._normalize_pull_request_head(head, _owner)
         payload = {
             "title": title,
             "body": body,
             "base": base,
-            "head": head or f"{_owner}-{_repo}-ai-gen-{hash(title) % 10000}",
+            "head": normalized_head or f"{_owner}:{_owner}-{_repo}-ai-gen-{hash(title) % 10000}",
         }
         return await self._request("POST", f"repos/{_owner}/{_repo}/pulls", payload)
 
@@ -242,11 +255,12 @@ class GiteaAPI:
         """Synchronously create a pull request."""
         _owner = owner or self.owner
         _repo = repo or self.repo
+        normalized_head = self._normalize_pull_request_head(head, _owner)
         payload = {
             "title": title,
             "body": body,
             "base": base,
-            "head": head or f"{_owner}-{_repo}-ai-gen-{hash(title) % 10000}",
+            "head": normalized_head or f"{_owner}:{_owner}-{_repo}-ai-gen-{hash(title) % 10000}",
         }
         return self._request_sync("POST", f"repos/{_owner}/{_repo}/pulls", payload)
 

ai_software_factory/agents/llm_service.py

@@ -3,6 +3,8 @@
 from __future__ import annotations
 
 import json
+from urllib import error as urllib_error
+from urllib import request as urllib_request
 
 try:
     from .gitea import GiteaAPI
@@ -183,6 +185,7 @@ class LLMServiceClient:
     def __init__(self, ollama_url: str | None = None, model: str | None = None):
         self.ollama_url = (ollama_url or settings.ollama_url).rstrip('/')
         self.model = model or settings.OLLAMA_MODEL
+        self.request_timeout_seconds = settings.llm_request_timeout_seconds
         self.toolbox = LLMToolbox()
         self.live_tool_executor = LLMLiveToolExecutor()
 
@@ -288,15 +291,39 @@ class LLMServiceClient:
         try:
             import aiohttp
 
-            async with aiohttp.ClientSession() as session:
+            async with aiohttp.ClientSession(timeout=aiohttp.ClientTimeout(total=self.request_timeout_seconds)) as session:
                 async with session.post(f'{self.ollama_url}/api/chat', json=request_payload) as resp:
                     payload = await resp.json()
                     if 200 <= resp.status < 300:
                         return (payload.get('message') or {}).get('content', ''), payload, None
                     return None, payload, str(payload.get('error') or payload)
         except Exception as exc:
+            if exc.__class__.__name__ == 'TimeoutError':
+                message = f'LLM request timed out after {self.request_timeout_seconds} seconds'
+                return None, {'error': message}, message
             return None, {'error': str(exc)}, str(exc)
 
+    @staticmethod
+    def extract_error_message(trace: dict | None) -> str | None:
+        """Extract the most useful provider error message from a trace payload."""
+        if not isinstance(trace, dict):
+            return None
+        raw_response = trace.get('raw_response') if isinstance(trace.get('raw_response'), dict) else {}
+        provider_response = raw_response.get('provider_response') if isinstance(raw_response.get('provider_response'), dict) else {}
+        candidate_errors = [
+            provider_response.get('error'),
+            raw_response.get('error'),
+            trace.get('error'),
+        ]
+        raw_responses = trace.get('raw_responses') if isinstance(trace.get('raw_responses'), list) else []
+        for payload in reversed(raw_responses):
+            if isinstance(payload, dict) and payload.get('error'):
+                candidate_errors.append(payload.get('error'))
+        for candidate in candidate_errors:
+            if candidate:
+                return str(candidate).strip()
+        return None
+
     def _compose_system_prompt(self, stage: str, stage_prompt: str) -> str:
         """Merge the stage prompt with configured guardrails."""
         sections = [stage_prompt.strip()] + self._guardrail_sections(stage)
@@ -372,6 +399,7 @@ class LLMServiceClient:
             'provider': 'ollama',
             'ollama_url': self.ollama_url,
             'model': self.model,
+            'request_timeout_seconds': self.request_timeout_seconds,
             'guardrails': {
                 'global': settings.llm_guardrail_prompt,
                 'request_interpretation': settings.llm_request_interpreter_guardrail_prompt,
@@ -391,4 +419,118 @@ class LLMServiceClient:
             'tool_context_limit': settings.llm_tool_context_limit,
             'max_tool_call_rounds': settings.llm_max_tool_call_rounds,
             'gitea_live_tools_configured': bool(settings.gitea_url and settings.gitea_token),
+        }
+
+    def health_check_sync(self) -> dict:
+        """Synchronously check Ollama reachability and configured model availability."""
+        if not self.ollama_url:
+            return {
+                'status': 'error',
+                'message': 'OLLAMA_URL is not configured.',
+                'ollama_url': 'Not configured',
+                'model': self.model,
+                'checks': [],
+                'suggestion': 'Set OLLAMA_URL to the reachable Ollama base URL.',
+            }
+
+        tags_url = f'{self.ollama_url}/api/tags'
+        try:
+            req = urllib_request.Request(tags_url, headers={'User-Agent': 'AI-Software-Factory'}, method='GET')
+            with urllib_request.urlopen(req, timeout=5) as resp:
+                raw_body = resp.read().decode('utf-8')
+                payload = json.loads(raw_body) if raw_body else {}
+        except urllib_error.HTTPError as exc:
+            body = exc.read().decode('utf-8') if exc.fp else ''
+            message = body or str(exc)
+            return {
+                'status': 'error',
+                'message': f'Ollama returned HTTP {exc.code}: {message}',
+                'ollama_url': self.ollama_url,
+                'model': self.model,
+                'checks': [
+                    {
+                        'name': 'api_tags',
+                        'ok': False,
+                        'status_code': exc.code,
+                        'url': tags_url,
+                        'message': message,
+                    }
+                ],
+                'suggestion': 'Verify OLLAMA_URL points to the Ollama service and that the API is reachable.',
+            }
+        except Exception as exc:
+            return {
+                'status': 'error',
+                'message': f'Unable to reach Ollama: {exc}',
+                'ollama_url': self.ollama_url,
+                'model': self.model,
+                'checks': [
+                    {
+                        'name': 'api_tags',
+                        'ok': False,
+                        'status_code': None,
+                        'url': tags_url,
+                        'message': str(exc),
+                    }
+                ],
+                'suggestion': 'Verify OLLAMA_URL resolves from the running factory process and that Ollama is listening on that address.',
+            }
+
+        models = payload.get('models') if isinstance(payload, dict) else []
+        model_names: list[str] = []
+        if isinstance(models, list):
+            for model_entry in models:
+                if not isinstance(model_entry, dict):
+                    continue
+                name = str(model_entry.get('name') or model_entry.get('model') or '').strip()
+                if name:
+                    model_names.append(name)
+
+        requested = (self.model or '').strip()
+        requested_base = requested.split(':', 1)[0]
+        model_available = any(
+            name == requested or name.startswith(f'{requested}:') or name.split(':', 1)[0] == requested_base
+            for name in model_names
+        )
+        checks = [
+            {
+                'name': 'api_tags',
+                'ok': True,
+                'status_code': 200,
+                'url': tags_url,
+                'message': f'Loaded {len(model_names)} model entries.',
+            },
+            {
+                'name': 'configured_model',
+                'ok': model_available,
+                'status_code': None,
+                'url': None,
+                'message': (
+                    f'Configured model {requested} is available.'
+                    if model_available else
+                    f'Configured model {requested} was not found in Ollama tags.'
+                ),
+            },
+        ]
+        if model_available:
+            return {
+                'status': 'success',
+                'message': f'Ollama is reachable and model {requested} is available.',
+                'ollama_url': self.ollama_url,
+                'model': requested,
+                'model_available': True,
+                'model_count': len(model_names),
+                'models': model_names[:10],
+                'checks': checks,
+            }
+        return {
+            'status': 'error',
+            'message': f'Ollama is reachable, but model {requested} is not available.',
+            'ollama_url': self.ollama_url,
+            'model': requested,
+            'model_available': False,
+            'model_count': len(model_names),
+            'models': model_names[:10],
+            'checks': checks,
+            'suggestion': f'Pull or configure the model {requested}, or update OLLAMA_MODEL to a model that exists in Ollama.',
         }

ai_software_factory/agents/orchestrator.py

@@ -124,7 +124,9 @@ class AgentOrchestrator:
                     self.repo_name = repository.get('name') or self.repo_name
                     self.repo_url = repository.get('url') or self.repo_url
                     git_state = latest_ui.get('git') if isinstance(latest_ui.get('git'), dict) else {}
-                    self.branch_name = git_state.get('active_branch') or self.branch_name
+                    persisted_active_branch = git_state.get('active_branch')
+                    if persisted_active_branch and persisted_active_branch not in {'main', 'master'}:
+                        self.branch_name = persisted_active_branch
             if self.prompt_text:
                 self.prompt_audit = self.db_manager.log_prompt_submission(
                     history_id=self.history.id,
@@ -133,6 +135,7 @@ class AgentOrchestrator:
                     features=self.features,
                     tech_stack=self.tech_stack,
                     actor_name=self.prompt_actor,
+                    source=self.prompt_actor,
                     related_issue={'number': self.related_issue_number} if self.related_issue_number is not None else None,
                     source_context=self.prompt_source_context,
                     routing=self.prompt_routing,
@@ -167,38 +170,18 @@ class AgentOrchestrator:
             ".gitignore": "__pycache__/\n*.pyc\n.venv/\n.pytest_cache/\n.mypy_cache/\n",
         }
 
-    def _fallback_generated_files(self) -> dict[str, str]:
-        """Deterministic fallback files when LLM generation is unavailable."""
-        feature_section = "\n".join(f"- {feature}" for feature in self.features) or "- None specified"
-        tech_section = "\n".join(f"- {tech}" for tech in self.tech_stack) or "- Python"
-        return {
-            "README.md": (
-                f"# {self.project_name}\n\n"
-                f"{self.description}\n\n"
-                "## Features\n"
-                f"{feature_section}\n\n"
-                "## Tech Stack\n"
-                f"{tech_section}\n"
-            ),
-            "requirements.txt": "fastapi\nuvicorn\npytest\n",
-            "main.py": (
-                "from fastapi import FastAPI\n\n"
-                "app = FastAPI(title=\"Generated App\")\n\n"
-                "@app.get('/')\n"
-                "def read_root():\n"
-                f"    return {{'name': '{self.project_name}', 'status': 'generated', 'features': {self.features!r}}}\n"
-            ),
-            "tests/test_app.py": (
-                "from main import read_root\n\n"
-                "def test_read_root():\n"
-                f"    assert read_root()['name'] == '{self.project_name}'\n"
-            ),
-        }
-
     def _build_pr_branch_name(self, project_id: str) -> str:
         """Build a stable branch name used until the PR is merged."""
         return f"ai/{project_id}"
 
+    def _should_use_pull_request_flow(self) -> bool:
+        """Return whether this run should deliver changes through a PR branch."""
+        return self.existing_history is not None or self.active_pull_request is not None
+
+    def _delivery_branch_name(self) -> str:
+        """Return the git branch used for the current delivery."""
+        return self.branch_name if self._should_use_pull_request_flow() else 'main'
+
     def _extract_issue_number(self, prompt_text: str | None) -> int | None:
         """Extract an issue reference from prompt text."""
         if not prompt_text:
@@ -215,7 +198,7 @@ class AgentOrchestrator:
         """Persist the current generation plan as an inspectable trace."""
         if not self.db_manager or not self.history or not self.prompt_audit:
             return
-        planned_files = list(self._static_files().keys()) + list(self._fallback_generated_files().keys())
+        planned_files = list(self._static_files().keys()) + ['README.md', 'requirements.txt', 'main.py', 'tests/test_app.py']
         self.db_manager.log_llm_trace(
             project_id=self.project_id,
             history_id=self.history.id,
@@ -227,7 +210,7 @@ class AgentOrchestrator:
             user_prompt=self.prompt_text or self.description,
             assistant_response=(
                 f"Planned files: {', '.join(planned_files)}. "
-                f"Target branch: {self.branch_name}. "
+                f"Target branch: {self._delivery_branch_name()}. "
                 f"Repository mode: {self.ui_manager.ui_data.get('repository', {}).get('mode', 'unknown')}."
                 + (
                     f" Linked issue: #{self.related_issue.get('number')} {self.related_issue.get('title')}."
@@ -238,7 +221,7 @@ class AgentOrchestrator:
                 'planned_files': planned_files,
                 'features': list(self.features),
                 'tech_stack': list(self.tech_stack),
-                'branch': self.branch_name,
+                'branch': self._delivery_branch_name(),
                 'repository': self.ui_manager.ui_data.get('repository', {}),
                 'related_issue': self.related_issue,
             },
@@ -334,7 +317,6 @@ class AgentOrchestrator:
 
     async def _generate_prompt_driven_files(self) -> tuple[dict[str, str], dict | None, bool]:
         """Use the configured LLM to generate prompt-specific project files."""
-        fallback_files = self._fallback_generated_files()
         workspace_context = self._collect_workspace_context()
         has_existing_files = bool(workspace_context.get('has_existing_files'))
         if has_existing_files:
@@ -388,11 +370,40 @@ class AgentOrchestrator:
             },
             expect_json=True,
         )
+        raw_generated_paths = self._extract_raw_generated_paths(content)
         generated_files = self._parse_generated_files(content)
-        if has_existing_files:
+        accepted_paths = list(generated_files.keys())
-            return generated_files, trace, True
+        rejected_paths = [path for path in raw_generated_paths if path not in accepted_paths]
-        merged_files = {**fallback_files, **generated_files}
+        generation_debug = {
-        return merged_files, trace, False
+            'raw_paths': raw_generated_paths,
+            'accepted_paths': accepted_paths,
+            'rejected_paths': rejected_paths,
+            'existing_workspace': has_existing_files,
+        }
+        self.ui_manager.ui_data['generation_debug'] = generation_debug
+        self._append_log(
+            'LLM returned file candidates: '
+            f"raw={raw_generated_paths or []}; accepted={accepted_paths or []}; rejected={rejected_paths or []}."
+        )
+        self._log_system_debug(
+            'generation',
+            'LLM file candidates '
+            f"raw={raw_generated_paths or []}; accepted={accepted_paths or []}; rejected={rejected_paths or []}; "
+            f"existing_workspace={has_existing_files}",
+        )
+        if not content:
+            detail = LLMServiceClient.extract_error_message(trace)
+            if detail:
+                raise RuntimeError(f'LLM code generation failed: {detail}')
+            raise RuntimeError('LLM code generation did not return a usable response.')
+        if not generated_files:
+            raise RuntimeError('LLM code generation did not return any writable files.')
+        if not has_existing_files:
+            required_files = {'README.md', 'requirements.txt', 'main.py', 'tests/test_app.py'}
+            missing_files = sorted(required_files - set(generated_files))
+            if missing_files:
+                raise RuntimeError(f"LLM code generation omitted required starter files: {', '.join(missing_files)}")
+        return generated_files, trace, has_existing_files
 
     async def _sync_issue_context(self) -> None:
         """Sync repository issues and resolve a linked issue from the prompt when present."""
@@ -552,11 +563,15 @@ class AgentOrchestrator:
                 self.ui_manager.ui_data.setdefault('git', {})['remote_error'] = str(exc)
                 self._append_log(f'Initial main push skipped: {exc}')
 
-        if self.git_manager.branch_exists(self.branch_name):
+        delivery_branch = self._delivery_branch_name()
-            self.git_manager.checkout_branch(self.branch_name)
+        if self._should_use_pull_request_flow():
+            if self.git_manager.branch_exists(self.branch_name):
+                self.git_manager.checkout_branch(self.branch_name)
+            else:
+                self.git_manager.checkout_branch(self.branch_name, create=True, start_point='main')
         else:
-            self.git_manager.checkout_branch(self.branch_name, create=True, start_point='main')
+            self.git_manager.checkout_branch('main')
-        self.ui_manager.ui_data.setdefault('git', {})['active_branch'] = self.branch_name
+        self.ui_manager.ui_data.setdefault('git', {})['active_branch'] = delivery_branch
 
     async def _ensure_pull_request(self) -> dict | None:
         """Create the project pull request on first delivery and reuse it later."""
@@ -573,6 +588,16 @@ class AgentOrchestrator:
             f"Prompt: {self.prompt_text or self.description}\n\n"
             f"Branch: {self.branch_name}"
         )
+        pull_request_debug = self.ui_manager.ui_data.setdefault('git', {}).setdefault('pull_request_debug', {})
+        pull_request_request = {
+            'owner': self.repo_owner,
+            'repo': self.repo_name,
+            'title': title,
+            'body': body,
+            'base': 'main',
+            'head': self.gitea_api._normalize_pull_request_head(self.branch_name, self.repo_owner) or self.branch_name,
+        }
+        pull_request_debug['request'] = pull_request_request
         result = await self.gitea_api.create_pull_request(
             title=title,
             body=body,
@@ -581,7 +606,9 @@ class AgentOrchestrator:
             base='main',
             head=self.branch_name,
         )
+        pull_request_debug['response'] = result
         if result.get('error'):
+            pull_request_debug['status'] = 'error'
             raise RuntimeError(f"Unable to create pull request: {result.get('error')}")
 
         pr_number = result.get('number') or result.get('id') or 0
@@ -596,6 +623,8 @@ class AgentOrchestrator:
             'merged': bool(result.get('merged')),
             'pr_state': result.get('state', 'open'),
         }
+        pull_request_debug['status'] = 'created'
+        pull_request_debug['resolved'] = pr_data
         if self.db_manager and self.history:
             self.db_manager.save_pr_data(self.history.id, pr_data)
         self.active_pull_request = self.db_manager.get_open_pull_request(project_id=self.project_id) if self.db_manager else pr_data
@@ -607,16 +636,17 @@ class AgentOrchestrator:
         repository = self.ui_manager.ui_data.get("repository") or {}
         if not self._repository_supports_remote_delivery(repository):
             return None
-        push_result = await self._push_branch(self.branch_name)
+        delivery_branch = self._delivery_branch_name()
+        push_result = await self._push_branch(delivery_branch)
         if push_result is None:
             return None
-        pull_request = await self._ensure_pull_request()
+        pull_request = await self._ensure_pull_request() if self._should_use_pull_request_flow() else None
         commit_url = self.gitea_api.build_commit_url(commit_hash, owner=self.repo_owner, repo=self.repo_name)
         compare_url = self.gitea_api.build_compare_url(base_commit, commit_hash, owner=self.repo_owner, repo=self.repo_name) if base_commit else None
         remote_record = {
             "status": "pushed",
             "remote": push_result.get('remote'),
-            "branch": self.branch_name,
+            "branch": delivery_branch,
             "commit_url": commit_url,
             "compare_url": compare_url,
             "changed_files": changed_files,
@@ -626,7 +656,10 @@ class AgentOrchestrator:
         repository["last_commit_url"] = commit_url
         if compare_url:
             repository["last_compare_url"] = compare_url
-        self._append_log(f"Pushed generated commit to {self.repo_owner}/{self.repo_name}.")
+        if pull_request:
+            self._append_log(f"Pushed generated commit to {self.repo_owner}/{self.repo_name} and updated the delivery pull request.")
+        else:
+            self._append_log(f"Pushed generated commit directly to {self.repo_owner}/{self.repo_name} on {delivery_branch}.")
         return remote_record
 
     def _build_diff_text(self, relative_path: str, previous_content: str, new_content: str) -> str:
@@ -647,6 +680,35 @@ class AgentOrchestrator:
         if self.db_manager and self.history:
             self.db_manager._log_action(self.history.id, "INFO", message)
 
+    def _log_system_debug(self, component: str, message: str, level: str = 'INFO') -> None:
+        """Persist a system-level debug breadcrumb for generation and git decisions."""
+        if not self.db_manager:
+            return
+        self.db_manager.log_system_event(component=component, level=level, message=f"{self.project_id}: {message}")
+
+    def _extract_raw_generated_paths(self, content: str | None) -> list[str]:
+        """Return all file paths proposed by the LLM response before safety filtering."""
+        if not content:
+            return []
+        try:
+            parsed = json.loads(content)
+        except Exception:
+            return []
+        raw_paths: list[str] = []
+        if isinstance(parsed, dict) and isinstance(parsed.get('files'), list):
+            for item in parsed['files']:
+                if not isinstance(item, dict):
+                    continue
+                path = str(item.get('path') or '').strip()
+                if path:
+                    raw_paths.append(path)
+        elif isinstance(parsed, dict):
+            for path in parsed.keys():
+                normalized_path = str(path).strip()
+                if normalized_path:
+                    raw_paths.append(normalized_path)
+        return raw_paths
+
     def _update_progress(self, progress: int, step: str, message: str) -> None:
         self.progress = progress
         self.current_step = step
@@ -781,7 +843,7 @@ class AgentOrchestrator:
             self._write_file(relative_path, content)
         if editing_existing_workspace and len(self.pending_code_changes) == change_count_before:
             raise RuntimeError('The LLM response did not produce any file changes for the existing project.')
-        fallback_used = bool(trace and trace.get('fallback_used')) or trace is None
+        fallback_used = bool(trace and trace.get('fallback_used'))
         if self.db_manager and self.history and self.prompt_audit and trace:
             self.db_manager.log_llm_trace(
                 project_id=self.project_id,
@@ -796,10 +858,7 @@ class AgentOrchestrator:
                 raw_response=trace.get('raw_response'),
                 fallback_used=fallback_used,
             )
-        if fallback_used:
+        self._append_log('Application files generated from the prompt with the configured LLM.')
-            self._append_log('LLM code generation was unavailable; used deterministic scaffolding fallback.')
-        else:
-            self._append_log('Application files generated from the prompt with the configured LLM.')
 
     async def _run_tests(self) -> None:
         """Run tests for the generated code."""
@@ -810,11 +869,25 @@ class AgentOrchestrator:
     async def _commit_to_git(self) -> None:
         """Commit changes to git."""
         unique_files = list(dict.fromkeys(self.changed_files))
+        git_debug = self.ui_manager.ui_data.setdefault('git', {})
         if not unique_files:
+            git_debug.update({
+                'commit_status': 'skipped',
+                'early_exit_reason': 'changed_files_empty',
+                'candidate_files': [],
+            })
+            self._append_log('Git commit skipped: no generated files were marked as changed.')
+            self._log_system_debug('git', 'Commit exited early because changed_files was empty.')
             return
         if not self.git_manager.is_git_available():
-            self.ui_manager.ui_data.setdefault('git', {})['error'] = 'git executable is not available in PATH'
+            git_debug.update({
+                'commit_status': 'error',
+                'early_exit_reason': 'git_unavailable',
+                'candidate_files': unique_files,
+                'error': 'git executable is not available in PATH',
+            })
             self._append_log('Git commit skipped: git executable is not available in PATH')
+            self._log_system_debug('git', 'Commit exited early because git is unavailable.', level='ERROR')
             return
 
         try:
@@ -822,7 +895,23 @@ class AgentOrchestrator:
                 self.git_manager.init_repo()
             base_commit = self.git_manager.current_head_or_none()
             self.git_manager.add_files(unique_files)
-            if not self.git_manager.get_status():
+            status_after_add = self.git_manager.get_status()
+            if not status_after_add:
+                git_debug.update({
+                    'commit_status': 'skipped',
+                    'early_exit_reason': 'clean_after_staging',
+                    'candidate_files': unique_files,
+                    'status_after_add': '',
+                })
+                self._append_log(
+                    'Git commit skipped: working tree was clean after staging candidate files '
+                    f'{unique_files}. No repository diff was created.'
+                )
+                self._log_system_debug(
+                    'git',
+                    'Commit exited early because git status was clean after staging '
+                    f'files={unique_files}',
+                )
                 return
 
             commit_message = f"AI generation for prompt: {self.project_name}"
@@ -833,13 +922,19 @@ class AgentOrchestrator:
                 "files": unique_files,
                 "timestamp": datetime.utcnow().isoformat(),
                 "scope": "local",
-                "branch": self.branch_name,
+                "branch": self._delivery_branch_name(),
             }
+            git_debug.update({
+                'commit_status': 'committed',
+                'early_exit_reason': None,
+                'candidate_files': unique_files,
+                'status_after_add': status_after_add,
+            })
             remote_record = None
             try:
                 remote_record = await self._push_remote_commit(commit_hash, commit_message, unique_files, base_commit)
             except (RuntimeError, subprocess.CalledProcessError, FileNotFoundError) as remote_exc:
-                self.ui_manager.ui_data.setdefault("git", {})["remote_error"] = str(remote_exc)
+                git_debug["remote_error"] = str(remote_exc)
                 self._append_log(f"Remote git push skipped: {remote_exc}")
 
             if remote_record:
@@ -849,8 +944,8 @@ class AgentOrchestrator:
                 if remote_record.get('pull_request'):
                     commit_record['pull_request'] = remote_record['pull_request']
                     self.ui_manager.ui_data['pull_request'] = remote_record['pull_request']
-            self.ui_manager.ui_data.setdefault("git", {})["latest_commit"] = commit_record
+            git_debug["latest_commit"] = commit_record
-            self.ui_manager.ui_data.setdefault("git", {})["commits"] = [commit_record]
+            git_debug["commits"] = [commit_record]
             self._append_log(f"Recorded git commit {commit_hash[:12]} for generated files.")
             if self.db_manager:
                 self.db_manager.log_commit(
@@ -896,7 +991,12 @@ class AgentOrchestrator:
                         commit_url=remote_record.get('commit_url') if remote_record else None,
                     )
         except (RuntimeError, subprocess.CalledProcessError, FileNotFoundError) as exc:
-            self.ui_manager.ui_data.setdefault("git", {})["error"] = str(exc)
+            git_debug.update({
+                'commit_status': 'error',
+                'early_exit_reason': 'commit_exception',
+                'candidate_files': unique_files,
+                'error': str(exc),
+            })
             self._append_log(f"Git commit skipped: {exc}")
 
     async def _create_pr(self) -> None:

ai_software_factory/agents/request_interpreter.py

@@ -15,6 +15,14 @@ except ImportError:
     from agents.llm_service import LLMServiceClient
 
 
+class RequestInterpretationError(RuntimeError):
+    """Raised when one LLM-driven request interpretation stage fails."""
+
+    def __init__(self, message: str, *, trace: dict | None = None):
+        super().__init__(message)
+        self.trace = trace or {}
+
+
 class RequestInterpreter:
     """Use Ollama to turn free-form text into a structured software request."""
 
@@ -28,9 +36,6 @@ class RequestInterpreter:
     GENERIC_PROJECT_NAME_WORDS = {
         'app', 'application', 'harness', 'platform', 'project', 'purpose', 'service', 'solution', 'suite', 'system', 'test', 'tool',
     }
-    PLACEHOLDER_PROJECT_NAME_WORDS = {
-        'generated project', 'new project', 'project', 'temporary name', 'temp name', 'placeholder', 'untitled project',
-    }
 
     def __init__(self, ollama_url: str | None = None, model: str | None = None):
         self.ollama_url = (ollama_url or settings.ollama_url).rstrip('/')
@@ -91,45 +96,45 @@ class RequestInterpreter:
             },
             expect_json=True,
         )
-        if content:
+        if not content:
-            try:
+            detail = self.llm_client.extract_error_message(trace)
-                parsed = json.loads(content)
+            if detail:
-                interpreted = self._normalize_interpreted_request(parsed, normalized)
+                raise RequestInterpretationError(f'LLM request interpretation failed: {detail}', trace=trace)
-                routing = self._normalize_routing(parsed.get('routing'), interpreted, compact_context)
+            raise RequestInterpretationError('LLM request interpretation did not return a usable response.', trace=trace)
-                naming_trace = None
-                if routing.get('intent') == 'new_project':
-                    interpreted, routing, naming_trace = await self._refine_new_project_identity(
-                        prompt_text=normalized,
-                        interpreted=interpreted,
-                        routing=routing,
-                        context=compact_context,
-                    )
-                trace['routing'] = routing
-                trace['context_excerpt'] = compact_context
-                if naming_trace is not None:
-                    trace['project_naming'] = naming_trace
-                return interpreted, trace
-            except Exception:
-                pass
 
-        interpreted, routing = self._heuristic_fallback(normalized, compact_context)
+        try:
+            parsed = json.loads(content)
+        except Exception as exc:
+            raise RequestInterpretationError('LLM request interpretation did not return valid JSON.', trace=trace) from exc
+
+        try:
+            interpreted = self._normalize_interpreted_request(parsed)
+            routing = self._normalize_routing(parsed.get('routing'), interpreted, compact_context)
+        except RuntimeError as exc:
+            raise RequestInterpretationError(str(exc), trace=trace) from exc
+        if routing.get('intent') == 'continue_project' and routing.get('project_name'):
+            interpreted['name'] = routing['project_name']
+        naming_trace = None
         if routing.get('intent') == 'new_project':
-            constraints = await self._collect_project_identity_constraints(compact_context)
+            try:
-            routing['repo_name'] = self._ensure_unique_repo_name(routing.get('repo_name') or interpreted.get('name') or 'project', constraints['repo_names'])
+                interpreted, routing, naming_trace = await self._refine_new_project_identity(
-        return interpreted, {
+                    prompt_text=normalized,
-            'stage': 'request_interpretation',
+                    interpreted=interpreted,
-            'provider': 'heuristic',
+                    routing=routing,
-            'model': self.model,
+                    context=compact_context,
-            'system_prompt': system_prompt,
+                )
-            'user_prompt': user_prompt,
+            except RequestInterpretationError as exc:
-            'assistant_response': json.dumps({'request': interpreted, 'routing': routing}),
+                combined_trace = dict(trace)
-            'raw_response': {'fallback': 'heuristic', 'llm_trace': trace.get('raw_response') if isinstance(trace, dict) else None},
+                combined_trace['routing'] = routing
-            'routing': routing,
+                combined_trace['context_excerpt'] = compact_context
-            'context_excerpt': compact_context,
+                if exc.trace:
-            'guardrails': trace.get('guardrails') if isinstance(trace, dict) else [],
+                    combined_trace['project_naming'] = exc.trace
-            'tool_context': trace.get('tool_context') if isinstance(trace, dict) else [],
+                raise RequestInterpretationError(str(exc), trace=combined_trace) from exc
-            'fallback_used': True,
+        trace['routing'] = routing
-        }
+        trace['context_excerpt'] = compact_context
+        if naming_trace is not None:
+            trace['project_naming'] = naming_trace
+        return interpreted, trace
 
     async def _refine_new_project_identity(
         self,
@@ -157,25 +162,25 @@ class RequestInterpreter:
             },
             expect_json=True,
         )
-        if content:
+        if not content:
-            try:
+            detail = self.llm_client.extract_error_message(trace)
-                fallback_name = self._preferred_project_name_fallback(prompt_text, interpreted.get('name'))
+            if detail:
-                parsed = json.loads(content)
+                raise RequestInterpretationError(f'LLM project naming failed: {detail}', trace=trace)
-                project_name, repo_name = self._normalize_project_identity(
+            raise RequestInterpretationError('LLM project naming did not return a usable response.', trace=trace)
-                    parsed,
-                    fallback_name=fallback_name,
-                )
-                repo_name = self._ensure_unique_repo_name(repo_name, constraints['repo_names'])
-                interpreted['name'] = project_name
-                routing['project_name'] = project_name
-                routing['repo_name'] = repo_name
-                return interpreted, routing, trace
-            except Exception:
-                pass
 
-        fallback_name = self._preferred_project_name_fallback(prompt_text, interpreted.get('name'))
+        try:
-        routing['project_name'] = fallback_name
+            parsed = json.loads(content)
-        routing['repo_name'] = self._ensure_unique_repo_name(self._derive_repo_name(fallback_name), constraints['repo_names'])
+        except Exception as exc:
+            raise RequestInterpretationError('LLM project naming did not return valid JSON.', trace=trace) from exc
+
+        try:
+            project_name, repo_name = self._normalize_project_identity(parsed)
+        except RuntimeError as exc:
+            raise RequestInterpretationError(str(exc), trace=trace) from exc
+        repo_name = self._ensure_unique_repo_name(repo_name, constraints['repo_names'])
+        interpreted['name'] = project_name
+        routing['project_name'] = project_name
+        routing['repo_name'] = repo_name
         return interpreted, routing, trace
 
     async def _collect_project_identity_constraints(self, context: dict) -> dict[str, set[str]]:
@@ -205,17 +210,19 @@ class RequestInterpreter:
             return set()
         return {str(repo.get('name')).strip() for repo in repos if repo.get('name')}
 
-    def _normalize_interpreted_request(self, interpreted: dict, original_prompt: str) -> dict:
+    def _normalize_interpreted_request(self, interpreted: dict) -> dict:
         """Normalize LLM output into the required request shape."""
         request_payload = interpreted.get('request') if isinstance(interpreted.get('request'), dict) else interpreted
-        name = str(interpreted.get('name') or '').strip() or self._derive_name(original_prompt)
+        if not isinstance(request_payload, dict):
-        if isinstance(request_payload, dict):
+            raise RuntimeError('LLM request interpretation did not include a request object.')
-            name = str(request_payload.get('name') or '').strip() or self._derive_name(original_prompt)
+        name = str(request_payload.get('name') or '').strip()
-        description = str((request_payload or {}).get('description') or '').strip() or original_prompt[:255]
+        description = str(request_payload.get('description') or '').strip()
-        features = self._normalize_list((request_payload or {}).get('features'))
+        if not name:
-        tech_stack = self._normalize_list((request_payload or {}).get('tech_stack'))
+            raise RuntimeError('LLM request interpretation did not provide a project name.')
-        if not features:
+        if not description:
-            features = ['core workflow based on free-form request']
+            raise RuntimeError('LLM request interpretation did not provide a project description.')
+        features = self._normalize_list(request_payload.get('features'))
+        tech_stack = self._normalize_list(request_payload.get('tech_stack'))
         return {
             'name': name[:255],
             'description': description[:255],
@@ -249,6 +256,9 @@ class RequestInterpreter:
     def _normalize_routing(self, routing: dict | None, interpreted: dict, context: dict) -> dict:
         """Normalize routing metadata returned by the LLM."""
         routing = routing or {}
+        intent = str(routing.get('intent') or '').strip()
+        if intent not in {'new_project', 'continue_project'}:
+            raise RuntimeError('LLM request interpretation did not provide a valid routing intent.')
         project_id = routing.get('project_id')
         project_name = routing.get('project_name')
         issue_number = routing.get('issue_number')
@@ -257,25 +267,32 @@ class RequestInterpreter:
         elif isinstance(issue_number, str) and issue_number.isdigit():
             issue_number = int(issue_number)
         matched_project = None
-        for project in context.get('projects', []):
+        if intent == 'continue_project':
-            if project_id and project.get('project_id') == project_id:
+            for project in context.get('projects', []):
-                matched_project = project
+                if project_id and project.get('project_id') == project_id:
-                break
+                    matched_project = project
-            if project_name and project.get('name') == project_name:
+                    break
-                matched_project = project
+                if project_name and project.get('name') == project_name:
-                break
+                    matched_project = project
-        intent = str(routing.get('intent') or '').strip() or ('continue_project' if matched_project else 'new_project')
+                    break
+        elif project_id:
+            matched_project = next(
+                (project for project in context.get('projects', []) if project.get('project_id') == project_id),
+                None,
+            )
+        if intent == 'continue_project' and matched_project is None:
+            raise RuntimeError('LLM selected continue_project without identifying a tracked project from prompt history.')
+        if intent == 'new_project' and matched_project is not None:
+            raise RuntimeError('LLM selected new_project while also pointing at an existing tracked project.')
         normalized = {
             'intent': intent,
             'project_id': matched_project.get('project_id') if matched_project else project_id,
             'project_name': matched_project.get('name') if matched_project else (project_name or interpreted.get('name')),
-            'repo_name': routing.get('repo_name') if intent == 'new_project' else None,
+            'repo_name': str(routing.get('repo_name') or '').strip() or None if intent == 'new_project' else None,
             'issue_number': issue_number,
-            'confidence': routing.get('confidence') or ('medium' if matched_project else 'low'),
+            'confidence': routing.get('confidence') or 'medium',
-            'reasoning_summary': routing.get('reasoning_summary') or ('Matched prior project context' if matched_project else 'No strong prior project match found'),
+            'reasoning_summary': routing.get('reasoning_summary') or '',
         }
-        if normalized['intent'] == 'new_project' and not normalized['repo_name']:
-            normalized['repo_name'] = self._derive_repo_name(normalized['project_name'] or interpreted.get('name') or 'Generated Project')
         return normalized
 
     def _normalize_list(self, value) -> list[str]:
@@ -285,42 +302,6 @@ class RequestInterpreter:
             return [item.strip() for item in value.split(',') if item.strip()]
         return []
 
-    def _derive_name(self, prompt_text: str) -> str:
-        """Derive a stable project name when the LLM does not provide one."""
-        first_line = prompt_text.splitlines()[0].strip()
-        quoted = re.search(r'["\']([^"\']{3,80})["\']', first_line)
-        if quoted:
-            return self._humanize_name(quoted.group(1))
-
-        noun_phrase = re.search(
-            r'(?:build|create|start|make|develop|generate|design|need|want)\s+'
-            r'(?:me\s+|us\s+|an?\s+|the\s+|new\s+|internal\s+|simple\s+|lightweight\s+|modern\s+|web\s+|mobile\s+)*'
-            r'([a-z0-9][a-z0-9\s-]{2,80}?(?:portal|dashboard|app|application|service|tool|system|platform|api|bot|assistant|website|site|workspace|tracker|manager|harness|runner|framework|suite|pipeline|lab))\b',
-            first_line,
-            flags=re.IGNORECASE,
-        )
-        if noun_phrase:
-            return self._humanize_name(noun_phrase.group(1))
-
-        focused_phrase = re.search(
-            r'(?:purpose\s+is\s+to\s+create\s+(?:an?\s+)?)'
-            r'([a-z0-9][a-z0-9\s-]{2,80}?(?:portal|dashboard|app|application|service|tool|system|platform|api|bot|assistant|website|site|workspace|tracker|manager|harness|runner|framework|suite|pipeline|lab))\b',
-            first_line,
-            flags=re.IGNORECASE,
-        )
-        if focused_phrase:
-            return self._humanize_name(focused_phrase.group(1))
-
-        cleaned = re.sub(r'[^A-Za-z0-9 ]+', ' ', first_line)
-        stopwords = {
-            'build', 'create', 'start', 'make', 'develop', 'generate', 'design', 'need', 'want', 'please', 'for', 'our', 'with', 'that', 'this',
-            'new', 'internal', 'simple', 'modern', 'web', 'mobile', 'app', 'application', 'tool', 'system',
-        }
-        tokens = [word for word in cleaned.split() if word and word.lower() not in stopwords]
-        if tokens:
-            return self._humanize_name(' '.join(tokens[:4]))
-        return 'Generated Project'
-
     def _humanize_name(self, raw_name: str) -> str:
         """Normalize a candidate project name into a readable title."""
         cleaned = re.sub(r'[^A-Za-z0-9\s-]+', ' ', raw_name).strip(' -')
@@ -397,15 +378,6 @@ class RequestInterpreter:
                 return False
         return True
 
-    def _preferred_project_name_fallback(self, prompt_text: str, interpreted_name: str | None) -> str:
-        """Pick the best fallback title when the earlier interpretation produced a placeholder."""
-        interpreted_clean = self._humanize_name(str(interpreted_name or '').strip()) if interpreted_name else ''
-        normalized_interpreted = interpreted_clean.lower()
-        if normalized_interpreted and normalized_interpreted not in self.PLACEHOLDER_PROJECT_NAME_WORDS:
-            if not (len(normalized_interpreted.split()) == 1 and normalized_interpreted in self.GENERIC_PROJECT_NAME_WORDS):
-                return interpreted_clean
-        return self._derive_name(prompt_text)
-
     def _ensure_unique_repo_name(self, repo_name: str, reserved_names: set[str]) -> str:
         """Choose a repository slug that does not collide with tracked or remote repositories."""
         base_name = self._derive_repo_name(repo_name)
@@ -416,76 +388,41 @@ class RequestInterpreter:
             suffix += 1
         return f'{base_name}-{suffix}'
 
-    def _normalize_project_identity(self, payload: dict, fallback_name: str) -> tuple[str, str]:
+    def _normalize_project_identity(self, payload: dict) -> tuple[str, str]:
-        """Normalize model-proposed project and repository naming."""
+        """Validate model-proposed project and repository naming."""
-        fallback_project_name = self._humanize_name(str(fallback_name or 'Generated Project'))
+        project_payload = payload.get('project') if isinstance(payload.get('project'), dict) else {}
-        project_candidate = str(payload.get('project_name') or payload.get('name') or '').strip()
+        repository_payload = payload.get('repository') if isinstance(payload.get('repository'), dict) else {}
-        project_name = fallback_project_name
+        project_candidate = str(
-        if project_candidate and self._should_use_project_name_candidate(project_candidate, fallback_project_name):
+            payload.get('project_name')
-            project_name = self._humanize_name(project_candidate)
+            or payload.get('name')
-        repo_candidate = str(payload.get('repo_name') or '').strip()
+            or payload.get('title')
-        repo_name = self._derive_repo_name(project_name)
+            or payload.get('display_name')
-        if repo_candidate and self._should_use_repo_name_candidate(repo_candidate, project_name):
+            or project_payload.get('project_name')
-            repo_name = self._derive_repo_name(repo_candidate)
+            or project_payload.get('name')
-        return project_name, repo_name
+            or project_payload.get('title')
-
+            or project_payload.get('display_name')
-    def _heuristic_fallback(self, prompt_text: str, context: dict | None = None) -> tuple[dict, dict]:
+            or ''
-        """Fallback request extraction when Ollama is unavailable."""
+        ).strip()
-        lowered = prompt_text.lower()
+        repo_candidate = str(
-        tech_candidates = [
+            payload.get('repo_name')
-            'python', 'fastapi', 'django', 'flask', 'postgresql', 'sqlite', 'react', 'vue', 'nicegui', 'docker'
+            or payload.get('repo')
-        ]
+            or payload.get('slug')
-        tech_stack = [candidate for candidate in tech_candidates if candidate in lowered]
+            or payload.get('repository_name')
-        sentences = [part.strip() for part in re.split(r'[\n\.]+', prompt_text) if part.strip()]
+            or payload.get('repository_slug')
-        features = sentences[:3] or ['Implement the user request from free-form text']
+            or repository_payload.get('repo_name')
-        interpreted = {
+            or repository_payload.get('name')
-            'name': self._derive_name(prompt_text),
+            or repository_payload.get('slug')
-            'description': sentences[0][:255] if sentences else prompt_text[:255],
+            or ''
-            'features': features,
+        ).strip()
-            'tech_stack': tech_stack,
+        if not project_candidate:
-        }
+            raise RuntimeError('LLM project naming did not provide a project name.')
-        routing = self._heuristic_routing(prompt_text, context or {})
+        if not repo_candidate:
-        if routing.get('project_name'):
+            raise RuntimeError('LLM project naming did not provide a repository slug.')
-            interpreted['name'] = routing['project_name']
+        if not self._should_use_project_name_candidate(project_candidate, project_candidate):
-        return interpreted, routing
+            raise RuntimeError('LLM project naming returned an unusable project name.')
-
+        if not self._should_use_repo_name_candidate(repo_candidate, project_candidate):
-    def _heuristic_routing(self, prompt_text: str, context: dict) -> dict:
+            raise RuntimeError('LLM project naming returned an unusable repository slug.')
-        """Best-effort routing when the LLM is unavailable."""
+        return self._humanize_name(project_candidate), self._derive_repo_name(repo_candidate)
-        lowered = prompt_text.lower()
-        explicit_new = any(token in lowered for token in ['new project', 'start a new project', 'create a new project', 'build a new app'])
-        referenced_issue = self._extract_issue_number(prompt_text)
-        recent_history = context.get('recent_chat_history', [])
-        projects = context.get('projects', [])
-        last_project_id = recent_history[0].get('project_id') if recent_history else None
-        last_issue = ((recent_history[0].get('related_issue') or {}).get('number') if recent_history else None)
-
-        matched_project = None
-        for project in projects:
-            name = (project.get('name') or '').lower()
-            repo = ((project.get('repository') or {}).get('name') or '').lower()
-            if name and name in lowered:
-                matched_project = project
-                break
-            if repo and repo in lowered:
-                matched_project = project
-                break
-        if matched_project is None and not explicit_new:
-            follow_up_tokens = ['also', 'continue', 'for this project', 'for that project', 'work on this', 'work on that', 'fix that', 'add this']
-            if any(token in lowered for token in follow_up_tokens) and last_project_id:
-                matched_project = next((project for project in projects if project.get('project_id') == last_project_id), None)
-        issue_number = referenced_issue
-        if issue_number is None and any(token in lowered for token in ['that issue', 'this issue', 'the issue']) and last_issue is not None:
-            issue_number = last_issue
-        intent = 'new_project' if explicit_new or matched_project is None else 'continue_project'
-        return {
-            'intent': intent,
-            'project_id': matched_project.get('project_id') if matched_project else None,
-            'project_name': matched_project.get('name') if matched_project else self._derive_name(prompt_text),
-            'repo_name': None if matched_project else self._derive_repo_name(self._derive_name(prompt_text)),
-            'issue_number': issue_number,
-            'confidence': 'medium' if matched_project or explicit_new else 'low',
-            'reasoning_summary': 'Heuristic routing from chat history and project names.',
-        }
 
     def _extract_issue_number(self, prompt_text: str) -> int | None:
         match = re.search(r'(?:#|issue\s+)(\d+)', prompt_text, flags=re.IGNORECASE)

ai_software_factory/config.py

@@ -222,6 +222,7 @@ class Settings(BaseSettings):
     # Ollama settings computed from environment
     OLLAMA_URL: str = "http://ollama:11434"
     OLLAMA_MODEL: str = "llama3"
+    LLM_REQUEST_TIMEOUT_SECONDS: int = 240
     LLM_GUARDRAIL_PROMPT: str = (
         "You are operating inside AI Software Factory. Follow the requested schema exactly, "
         "treat provided tool outputs as authoritative, and do not invent repositories, issues, pull requests, or delivery facts."
@@ -613,6 +614,11 @@ class Settings(BaseSettings):
         """Get the maximum number of queued prompts to process in one batch."""
         return max(int(_resolve_runtime_setting_value('PROMPT_QUEUE_MAX_BATCH_SIZE', self.PROMPT_QUEUE_MAX_BATCH_SIZE)), 1)
 
+    @property
+    def llm_request_timeout_seconds(self) -> int:
+        """Get the outbound provider timeout for one LLM request."""
+        return max(int(_resolve_runtime_setting_value('LLM_REQUEST_TIMEOUT_SECONDS', self.LLM_REQUEST_TIMEOUT_SECONDS)), 1)
+
     @property
     def projects_root(self) -> Path:
         """Get the root directory for generated project artifacts."""

ai_software_factory/dashboard_ui.py

@@ -214,6 +214,70 @@ def _render_commit_list(commits: list[dict]) -> None:
                     ui.link('Open compare view', compare_url, new_tab=True)
 
 
+def _render_generation_diagnostics(ui_data: dict | None) -> None:
+    """Render generation and git diagnostics from the latest UI snapshot."""
+    snapshot = ui_data if isinstance(ui_data, dict) else {}
+    generation_debug = snapshot.get('generation_debug') if isinstance(snapshot.get('generation_debug'), dict) else {}
+    git_debug = snapshot.get('git') if isinstance(snapshot.get('git'), dict) else {}
+
+    if not generation_debug and not git_debug:
+        ui.label('No generation diagnostics captured yet.').classes('factory-muted')
+        return
+
+    def _render_path_row(label: str, values: list[str]) -> None:
+        text = ', '.join(values) if values else 'none'
+        ui.label(f'{label}: {text}').classes('factory-muted' if values else 'factory-code')
+
+    with ui.column().classes('gap-3 w-full'):
+        if generation_debug:
+            with ui.column().classes('gap-1'):
+                ui.label('Generation filtering').style('font-weight: 700; color: #2f241d;')
+                ui.label(
+                    'Existing workspace: '
+                    + ('yes' if generation_debug.get('existing_workspace') else 'no')
+                ).classes('factory-muted')
+                _render_path_row('Raw paths', generation_debug.get('raw_paths') or [])
+                _render_path_row('Accepted paths', generation_debug.get('accepted_paths') or [])
+                _render_path_row('Rejected paths', generation_debug.get('rejected_paths') or [])
+        if git_debug:
+            with ui.column().classes('gap-1'):
+                ui.label('Git outcome').style('font-weight: 700; color: #2f241d;')
+                if git_debug.get('commit_status'):
+                    with ui.row().classes('items-center gap-2'):
+                        ui.label(git_debug['commit_status']).classes('factory-chip')
+                        if git_debug.get('early_exit_reason'):
+                            ui.label(git_debug['early_exit_reason']).classes('factory-chip')
+                if git_debug.get('candidate_files') is not None:
+                    _render_path_row('Candidate files', git_debug.get('candidate_files') or [])
+                latest_commit = git_debug.get('latest_commit') if isinstance(git_debug.get('latest_commit'), dict) else {}
+                if latest_commit:
+                    ui.label(
+                        f"Latest commit: {(latest_commit.get('hash') or 'unknown')[:12]} · {latest_commit.get('scope') or 'local'}"
+                    ).classes('factory-muted')
+                if git_debug.get('status_after_add'):
+                    with ui.expansion('Git status after staging').classes('w-full q-mt-sm'):
+                        ui.label(str(git_debug['status_after_add'])).classes('factory-code')
+                if git_debug.get('remote_error'):
+                    ui.label(f"Remote push error: {git_debug['remote_error']}").classes('factory-code')
+                if git_debug.get('error'):
+                    ui.label(f"Git error: {git_debug['error']}").classes('factory-code')
+                pull_request_debug = git_debug.get('pull_request_debug') if isinstance(git_debug.get('pull_request_debug'), dict) else {}
+                if pull_request_debug:
+                    ui.label('Pull request creation').style('font-weight: 700; color: #2f241d;')
+                    if pull_request_debug.get('status'):
+                        ui.label(str(pull_request_debug['status'])).classes('factory-chip')
+                    if pull_request_debug.get('request'):
+                        with ui.expansion('PR request payload').classes('w-full q-mt-sm'):
+                            ui.label(json.dumps(pull_request_debug['request'], indent=2, sort_keys=True)).classes('factory-code')
+                    if pull_request_debug.get('response'):
+                        with ui.expansion('PR API response').classes('w-full q-mt-sm'):
+                            ui.label(json.dumps(pull_request_debug['response'], indent=2, sort_keys=True)).classes('factory-code')
+                    if pull_request_debug.get('resolved'):
+                        resolved = pull_request_debug['resolved']
+                        if resolved.get('pr_url'):
+                            ui.link('Open pull request', resolved['pr_url'], new_tab=True).classes('factory-code')
+
+
 def _render_timeline(events: list[dict]) -> None:
     """Render a mixed project timeline."""
     if not events:
@@ -481,6 +545,52 @@ def _render_change_list(changes: list[dict]) -> None:
                     _render_side_by_side_diff(change['diff_text'])
 
 
+def _extract_llm_trace_error(trace: dict) -> str | None:
+    """Extract one useful failure message from a persisted LLM trace."""
+    if not isinstance(trace, dict):
+        return None
+    raw_response = trace.get('raw_response') if isinstance(trace.get('raw_response'), dict) else {}
+    provider_trace = raw_response.get('provider_trace') if isinstance(raw_response.get('provider_trace'), dict) else {}
+    provider_response = raw_response.get('provider_response') if isinstance(raw_response.get('provider_response'), dict) else {}
+    nested_provider_response = provider_trace.get('provider_response') if isinstance(provider_trace.get('provider_response'), dict) else {}
+    candidates = [
+        raw_response.get('failure_message'),
+        raw_response.get('error'),
+        provider_response.get('error'),
+        provider_trace.get('error'),
+        nested_provider_response.get('error'),
+    ]
+    for candidate in candidates:
+        if candidate:
+            return str(candidate)
+    return None
+
+
+def _build_llm_insights(traces: list[dict]) -> dict:
+    """Summarize recent LLM activity for dashboard visibility."""
+    normalized = [trace for trace in traces if isinstance(trace, dict)]
+    by_stage: dict[str, int] = {}
+    error_by_stage: dict[str, int] = {}
+    recent_errors: list[dict] = []
+    fallback_traces = 0
+    for trace in normalized:
+        stage = str(trace.get('stage') or 'unknown')
+        by_stage[stage] = by_stage.get(stage, 0) + 1
+        if trace.get('fallback_used'):
+            fallback_traces += 1
+        if _extract_llm_trace_error(trace):
+            error_by_stage[stage] = error_by_stage.get(stage, 0) + 1
+            recent_errors.append(trace)
+    return {
+        'total_traces': len(normalized),
+        'error_traces': len(recent_errors),
+        'fallback_traces': fallback_traces,
+        'by_stage': by_stage,
+        'error_by_stage': error_by_stage,
+        'recent_errors': recent_errors[:8],
+    }
+
+
 def _render_llm_traces(traces: list[dict]) -> None:
     """Render persisted LLM request/response traces for a prompt."""
     if not traces:
@@ -496,12 +606,17 @@ def _render_llm_traces(traces: list[dict]) -> None:
                 ui.label(f'{provider}:{model}').classes('factory-chip')
             if trace.get('fallback_used'):
                 ui.label('Fallback path used').classes('factory-chip')
+            error_message = _extract_llm_trace_error(trace)
+            if error_message:
+                ui.label(error_message).classes('factory-chip')
             with ui.expansion('System prompt').classes('w-full q-mt-sm'):
                 ui.label(trace.get('system_prompt') or 'No system prompt recorded').classes('factory-code')
             with ui.expansion('User prompt').classes('w-full q-mt-sm'):
                 ui.label(trace.get('user_prompt') or 'No user prompt recorded').classes('factory-code')
             with ui.expansion('Assistant response').classes('w-full q-mt-sm'):
                 ui.label(trace.get('assistant_response') or 'No assistant response recorded').classes('factory-code')
+            with ui.expansion('Raw provider response').classes('w-full q-mt-sm'):
+                ui.label(json.dumps(trace.get('raw_response'), indent=2, sort_keys=True) if trace.get('raw_response') is not None else 'No raw response recorded').classes('factory-code')
 
 
 def _filter_llm_traces(traces: list[dict], stage: str, model: str, search_query: str) -> list[dict]:
@@ -661,6 +776,20 @@ def _load_home_assistant_health_snapshot() -> dict:
         }
 
 
+def _load_ollama_health_snapshot() -> dict:
+    """Load an Ollama health snapshot for UI rendering."""
+    try:
+        return LLMServiceClient().health_check_sync()
+    except Exception as exc:
+        return {
+            'status': 'error',
+            'message': f'Unable to run Ollama health checks: {exc}',
+            'ollama_url': settings.ollama_url or 'Not configured',
+            'model': settings.OLLAMA_MODEL,
+            'checks': [],
+        }
+
+
 def _add_dashboard_styles() -> None:
     """Register shared dashboard styles."""
     ui.add_head_html(
@@ -757,6 +886,7 @@ def _render_confirmation_dialog(title: str, message: str, confirm_label: str, on
 def _render_health_panels() -> None:
     """Render application, integration, and queue health panels."""
     runtime = get_database_runtime_summary()
+    ollama_health = _load_ollama_health_snapshot()
     n8n_health = _load_n8n_health_snapshot()
     gitea_health = _load_gitea_health_snapshot()
     home_assistant_health = _load_home_assistant_health_snapshot()
@@ -779,6 +909,33 @@ def _render_health_panels() -> None:
                     ui.label(label).classes('factory-muted')
                     ui.label(str(value)).style('font-weight: 600; color: #3a281a;')
 
+        with ui.card().classes('factory-panel q-pa-lg'):
+            ui.label('Ollama / LLM').style('font-size: 1.25rem; font-weight: 700; color: #3a281a;')
+            ui.label(ollama_health.get('status', 'unknown').upper()).classes('factory-chip')
+            ui.label(ollama_health.get('message', 'No Ollama status available.')).classes('factory-muted q-mt-sm')
+            rows = [
+                ('Ollama URL', ollama_health.get('ollama_url') or 'Not configured'),
+                ('Configured Model', ollama_health.get('model') or 'Not configured'),
+                ('Model Available', 'yes' if ollama_health.get('model_available') else 'no'),
+                ('Visible Models', ollama_health.get('model_count') if ollama_health.get('model_count') is not None else 'unknown'),
+            ]
+            for label, value in rows:
+                with ui.row().classes('justify-between w-full q-mt-sm'):
+                    ui.label(label).classes('factory-muted')
+                    ui.label(str(value)).style('font-weight: 600; color: #3a281a;')
+            if ollama_health.get('models'):
+                ui.label('Reported Models').style('font-size: 1rem; font-weight: 700; color: #3a281a; margin-top: 12px;')
+                ui.label(', '.join(str(model) for model in ollama_health.get('models', []))).classes('factory-muted')
+            if ollama_health.get('suggestion'):
+                ui.label(ollama_health['suggestion']).classes('factory-chip q-mt-md')
+            for check in ollama_health.get('checks', []):
+                status = 'OK' if check.get('ok') else 'FAIL'
+                ui.markdown(
+                    f"- **{escape(check.get('name', 'check'))}** · {status} · {escape(str(check.get('status_code') or 'n/a'))} · {escape(check.get('url') or 'unknown url')}"
+                )
+                if check.get('message'):
+                    ui.label(check['message']).classes('factory-muted')
+
         with ui.card().classes('factory-panel q-pa-lg'):
             ui.label('n8n Connection Status').style('font-size: 1.25rem; font-weight: 700; color: #3a281a;')
             status_label = n8n_health.get('status', 'unknown').upper()
@@ -866,7 +1023,7 @@ def create_health_page() -> None:
             with ui.row().classes('items-center justify-between w-full'):
                 with ui.column().classes('gap-1'):
                     ui.label('Factory Health').style('font-size: 2rem; font-weight: 800; color: #302116;')
-                    ui.label('Current application and n8n connectivity diagnostics.').classes('factory-muted')
+                    ui.label('Current application, Ollama, and integration connectivity diagnostics.').classes('factory-muted')
                 with ui.row().classes('items-center gap-2'):
                     ui.link('Back to Dashboard', '/')
                     ui.link('Refresh Health', '/health-ui')
@@ -1367,6 +1524,7 @@ def create_dashboard():
             }
         projects = snapshot['projects']
         all_llm_traces = [trace for project_bundle in projects for trace in project_bundle.get('llm_traces', [])]
+        recent_llm_traces = snapshot.get('recent_llm_traces', [])
         return {
             'snapshot': snapshot,
             'summary': snapshot['summary'],
@@ -1384,6 +1542,8 @@ def create_dashboard():
             'discovered_repositories': discovered_repositories,
             'prompt_settings': prompt_settings,
             'runtime_settings': runtime_settings,
+            'recent_llm_traces': recent_llm_traces,
+            'llm_insights': _build_llm_insights(recent_llm_traces),
             'llm_stage_options': [''] + sorted({trace.get('stage') for trace in all_llm_traces if trace.get('stage')}),
             'llm_model_options': [''] + sorted({trace.get('model') for trace in all_llm_traces if trace.get('model')}),
             'project_repository_map': {
@@ -1576,6 +1736,9 @@ def create_dashboard():
                             'Sync Repo Activity',
                             on_click=lambda _=None, project_id=project['project_id']: sync_project_repository_action(project_id),
                         ).props('outline color=secondary').classes('q-mt-md')
+                    with ui.card().classes('q-pa-md'):
+                        ui.label('Generation Diagnostics').style('font-weight: 700; color: #3a281a;')
+                        _render_generation_diagnostics(project_bundle.get('ui_data'))
 
     @ui.refreshable
     def render_archived_panel() -> None:
@@ -1642,6 +1805,9 @@ def create_dashboard():
                     with ui.card().classes('q-pa-md'):
                         ui.label('Repository').style('font-weight: 700; color: #3a281a;')
                         _render_repository_block(project_bundle.get('repository') or project.get('repository'))
+                    with ui.card().classes('q-pa-md'):
+                        ui.label('Generation Diagnostics').style('font-weight: 700; color: #3a281a;')
+                        _render_generation_diagnostics(project_bundle.get('ui_data'))
                     with ui.card().classes('q-pa-md'):
                         ui.label('Prompt').style('font-weight: 700; color: #3a281a;')
                         prompts = project_bundle.get('prompts', [])
@@ -1842,6 +2008,7 @@ def create_dashboard():
             return
         system_logs = view_model['system_logs']
         llm_runtime = view_model['llm_runtime']
+        llm_insights = view_model.get('llm_insights', {})
         discovered_repositories = view_model['discovered_repositories']
         prompt_settings = view_model.get('prompt_settings', [])
         runtime_settings = view_model.get('runtime_settings', [])
@@ -1859,6 +2026,7 @@ def create_dashboard():
                     ('Provider', llm_runtime.get('provider')),
                     ('Model', llm_runtime.get('model')),
                     ('Ollama URL', llm_runtime.get('ollama_url')),
+                    ('Request Timeout', str(llm_runtime.get('request_timeout_seconds') or 'n/a')),
                     ('Tool Context Limit', str(llm_runtime.get('tool_context_limit'))),
                     ('Max Tool Call Rounds', str(llm_runtime.get('max_tool_call_rounds'))),
                     ('Live Gitea Tools Configured', 'yes' if llm_runtime.get('gitea_live_tools_configured') else 'no'),
@@ -1895,6 +2063,25 @@ def create_dashboard():
                     for label, text in system_prompts.items():
                         ui.label(label.replace('_', ' ').title()).classes('factory-muted q-mt-sm')
                         ui.label(text or 'Not configured').classes('factory-code')
+            with ui.card().classes('factory-panel q-pa-lg'):
+                ui.label('LLM Insights').style('font-size: 1.25rem; font-weight: 700; color: #3a281a;')
+                for label, value in [
+                    ('Recent Traces', llm_insights.get('total_traces', 0)),
+                    ('Recent Errors', llm_insights.get('error_traces', 0)),
+                    ('Fallback Traces', llm_insights.get('fallback_traces', 0)),
+                ]:
+                    with ui.row().classes('justify-between w-full q-mt-sm'):
+                        ui.label(label).classes('factory-muted')
+                        ui.label(str(value)).style('font-weight: 600; color: #3a281a;')
+                if llm_insights.get('by_stage'):
+                    ui.label('Trace Volume By Stage').style('font-weight: 700; color: #3a281a; margin-top: 12px;')
+                    for stage_name, count in sorted(llm_insights.get('by_stage', {}).items()):
+                        error_count = llm_insights.get('error_by_stage', {}).get(stage_name, 0)
+                        ui.markdown(f"- **{stage_name}**: {count} trace(s), {error_count} error(s)")
+                if llm_insights.get('recent_errors'):
+                    ui.label('Recent LLM Errors').style('font-weight: 700; color: #3a281a; margin-top: 12px;')
+                    for trace in llm_insights.get('recent_errors', []):
+                        ui.markdown(f"- **{trace.get('stage') or 'llm'}** · {trace.get('timestamp') or 'n/a'} · {escape(_extract_llm_trace_error(trace) or 'Unknown error')}")
             with ui.card().classes('factory-panel q-pa-lg'):
                 ui.label('Home Assistant and Queue Settings').style('font-size: 1.25rem; font-weight: 700; color: #3a281a;')
                 ui.label('Keep only the Home Assistant base URL and access token in the environment. Entity ids, thresholds, and queue behavior are edited here and persisted in the database.').classes('factory-muted')

ai_software_factory/main.py

@@ -31,11 +31,12 @@ try:
     from .agents.change_summary import ChangeSummaryGenerator
     from .agents.database_manager import DatabaseManager
     from .agents.home_assistant import HomeAssistantAgent
-    from .agents.request_interpreter import RequestInterpreter
+    from .agents.request_interpreter import RequestInterpreter, RequestInterpretationError
     from .agents.llm_service import LLMServiceClient
     from .agents.orchestrator import AgentOrchestrator
     from .agents.n8n_setup import N8NSetupAgent
     from .agents.prompt_workflow import PromptWorkflowManager
+    from .agents.telegram import TelegramHandler
     from .agents.ui_manager import UIManager
     from .models import ProjectHistory, ProjectLog, SystemLog
 except ImportError:
@@ -44,11 +45,12 @@ except ImportError:
     from agents.change_summary import ChangeSummaryGenerator
     from agents.database_manager import DatabaseManager
     from agents.home_assistant import HomeAssistantAgent
-    from agents.request_interpreter import RequestInterpreter
+    from agents.request_interpreter import RequestInterpreter, RequestInterpretationError
     from agents.llm_service import LLMServiceClient
     from agents.orchestrator import AgentOrchestrator
     from agents.n8n_setup import N8NSetupAgent
     from agents.prompt_workflow import PromptWorkflowManager
+    from agents.telegram import TelegramHandler
     from agents.ui_manager import UIManager
     from models import ProjectHistory, ProjectLog, SystemLog
 
@@ -78,6 +80,7 @@ app = FastAPI(lifespan=lifespan)
 
 DbSession = Annotated[Session, Depends(database_module.get_db)]
 PROJECT_ID_PATTERN = re.compile(r"[^a-z0-9]+")
+UNASSIGNED_LLM_TRACE_PROJECT_ID = '__unassigned__'
 
 
 class SoftwareRequest(BaseModel):
@@ -187,7 +190,6 @@ async def _derive_project_id_for_request(
 ) -> tuple[str, dict | None]:
     """Derive a stable project id for a newly created project."""
     reserved_ids = {str(project.get('project_id')).strip() for project in existing_projects if project.get('project_id')}
-    fallback_id = _ensure_unique_identifier((prompt_routing or {}).get('project_name') or request.name, reserved_ids)
     user_prompt = (
         f"Original user prompt:\n{prompt_text}\n\n"
         f"Structured request:\n{json.dumps({'name': request.name, 'description': request.description, 'features': request.features, 'tech_stack': request.tech_stack}, indent=2)}\n\n"
@@ -202,14 +204,19 @@ async def _derive_project_id_for_request(
         tool_context_input={'projects': existing_projects},
         expect_json=True,
     )
-    if content:
+    if not content:
-        try:
+        detail = LLMServiceClient.extract_error_message(trace)
-            parsed = json.loads(content)
+        if detail:
-            candidate = parsed.get('project_id') or parsed.get('slug') or request.name
+            raise RuntimeError(f'LLM project id naming failed: {detail}')
-            return _ensure_unique_identifier(str(candidate), reserved_ids), trace
+        raise RuntimeError('LLM project id naming did not return a usable response.')
-        except Exception:
+    try:
-            pass
+        parsed = json.loads(content)
-    return fallback_id, trace
+    except Exception as exc:
+        raise RuntimeError('LLM project id naming did not return valid JSON.') from exc
+    candidate = str(parsed.get('project_id') or parsed.get('slug') or '').strip()
+    if not candidate:
+        raise RuntimeError('LLM project id naming did not provide a project id.')
+    return _ensure_unique_identifier(candidate, reserved_ids), trace
 
 
 def _serialize_project(history: ProjectHistory) -> dict:
@@ -241,6 +248,74 @@ def _serialize_project_log(log: ProjectLog) -> dict:
     }
 
 
+def _ensure_summary_mentions_pull_request(summary_message: str, pull_request: dict | None) -> str:
+    """Append the pull request URL to chat summaries when one exists."""
+    if not isinstance(pull_request, dict):
+        return summary_message
+    pr_url = (pull_request.get('pr_url') or '').strip()
+    if not pr_url or pr_url in summary_message:
+        return summary_message
+    separator = '' if summary_message.endswith(('.', '!', '?')) else '.'
+    return f"{summary_message}{separator} Review PR: {pr_url}"
+
+
+def _should_queue_telegram_request(request: FreeformSoftwareRequest) -> bool:
+    """Return whether a Telegram request should be accepted for background processing."""
+    return (
+        request.source == 'telegram'
+        and bool(request.chat_id)
+        and bool(database_module.settings.telegram_bot_token)
+        and not request.process_now
+    )
+
+
+def _schedule_prompt_queue_processing() -> None:
+    """Kick off background queue processing without blocking the current HTTP request."""
+    if database_module.settings.prompt_queue_enabled and not database_module.settings.prompt_queue_auto_process:
+        return
+    limit = database_module.settings.prompt_queue_max_batch_size if database_module.settings.prompt_queue_enabled else 1
+    force = database_module.settings.prompt_queue_force_process if database_module.settings.prompt_queue_enabled else True
+    task = asyncio.create_task(_process_prompt_queue_batch(limit=limit, force=force))
+
+    def _log_task_result(completed_task: asyncio.Task) -> None:
+        try:
+            completed_task.result()
+        except Exception as exc:
+            db = database_module.get_db_sync()
+            try:
+                DatabaseManager(db).log_system_event('prompt-queue', 'ERROR', f'Background queue processing failed: {exc}')
+            finally:
+                db.close()
+
+    task.add_done_callback(_log_task_result)
+
+
+async def _notify_telegram_queue_result(request: FreeformSoftwareRequest, *, response: dict | None = None, error_message: str | None = None) -> None:
+    """Send the final queued result back to Telegram when chat metadata is available."""
+    if request.source != 'telegram' or not request.chat_id or not database_module.settings.telegram_bot_token:
+        return
+    if response is not None:
+        message = (
+            response.get('summary_message')
+            or (response.get('data') or {}).get('summary_message')
+            or response.get('message')
+            or 'Software generation completed.'
+        )
+    else:
+        message = f"Software generation failed: {error_message or 'Unknown error'}"
+    result = await TelegramHandler(webhook_url=database_module.settings.backend_public_url).send_message(
+        bot_token=database_module.settings.telegram_bot_token,
+        chat_id=request.chat_id,
+        text=message,
+    )
+    if result.get('status') == 'error':
+        db = database_module.get_db_sync()
+        try:
+            DatabaseManager(db).log_system_event('telegram', 'ERROR', f"Unable to send queued Telegram update: {result.get('message')}")
+        finally:
+            db.close()
+
+
 def _serialize_system_log(log: SystemLog) -> dict:
     """Serialize a system log row."""
     return {
@@ -271,6 +346,51 @@ def _compose_prompt_text(request: SoftwareRequest) -> str:
     )
 
 
+def _generation_error_payload(
+    *,
+    message: str,
+    request: SoftwareRequest | None = None,
+    source: dict | None = None,
+    interpreted_request: dict | None = None,
+    routing: dict | None = None,
+) -> dict:
+    """Return a workflow-safe JSON payload for expected generation failures."""
+    response = {
+        'status': 'error',
+        'message': message,
+        'error': message,
+        'summary_message': message,
+        'summary_metadata': {
+            'provider': None,
+            'model': None,
+            'fallback_used': False,
+        },
+        'data': {
+            'history_id': None,
+            'project_id': None,
+            'name': request.name if request is not None else (interpreted_request or {}).get('name'),
+            'description': request.description if request is not None else (interpreted_request or {}).get('description'),
+            'status': 'error',
+            'progress': 0,
+            'message': message,
+            'current_step': None,
+            'error_message': message,
+            'logs': [],
+            'changed_files': [],
+            'repository': None,
+            'pull_request': None,
+            'summary_message': message,
+        },
+    }
+    if source is not None:
+        response['source'] = source
+    if interpreted_request is not None:
+        response['interpreted_request'] = interpreted_request
+    if routing is not None:
+        response['routing'] = routing
+    return response
+
+
 async def _run_generation(
     request: SoftwareRequest,
     db: Session,
@@ -306,7 +426,7 @@ async def _run_generation(
     resolved_prompt_text = prompt_text or _compose_prompt_text(request)
     if preferred_project_id and reusable_history is not None:
         project_id = reusable_history.project_id
-    elif reusable_history and not is_explicit_new_project and manager.get_open_pull_request(project_id=reusable_history.project_id):
+    elif reusable_history and not is_explicit_new_project:
         project_id = reusable_history.project_id
     else:
         if is_explicit_new_project or prompt_text:
@@ -348,6 +468,8 @@ async def _run_generation(
     response_data = _serialize_project(history)
     response_data['logs'] = [_serialize_project_log(log) for log in project_logs]
     response_data['ui_data'] = result.get('ui_data')
+    response_data['generation_debug'] = ((result.get('ui_data') or {}).get('generation_debug'))
+    response_data['git_debug'] = ((result.get('ui_data') or {}).get('git'))
     response_data['features'] = request.features
     response_data['tech_stack'] = request.tech_stack
     response_data['project_root'] = result.get('project_root', str(_project_root(project_id)))
@@ -389,6 +511,7 @@ async def _run_generation(
         'logs': [log.get('message', '') for log in response_data.get('logs', []) if isinstance(log, dict)],
     }
     summary_message, summary_trace = await ChangeSummaryGenerator().summarize_with_trace(summary_context)
+    summary_message = _ensure_summary_mentions_pull_request(summary_message, response_data.get('pull_request'))
     if orchestrator.db_manager and orchestrator.history and orchestrator.prompt_audit:
         orchestrator.db_manager.log_llm_trace(
             project_id=project_id,
@@ -505,6 +628,11 @@ def _get_home_assistant_health() -> dict:
     return _create_home_assistant_agent().health_check_sync()
 
 
+def _get_ollama_health() -> dict:
+    """Return current Ollama connectivity diagnostics."""
+    return LLMServiceClient().health_check_sync()
+
+
 async def _get_queue_gate_status(force: bool = False) -> dict:
     """Return whether queued prompts may be processed now."""
     if not database_module.settings.prompt_queue_enabled:
@@ -546,6 +674,48 @@ async def _interpret_freeform_request(request: FreeformSoftwareRequest, manager:
     return SoftwareRequest(**interpreted), routing, interpretation_trace
 
 
+def _persist_llm_trace(manager: DatabaseManager, *, project_id: str, trace: dict, prompt_id: int | None = None, history_id: int | None = None) -> None:
+    """Persist one LLM trace payload when enough metadata is available."""
+    if not isinstance(trace, dict) or not trace.get('stage'):
+        return
+    manager.log_llm_trace(
+        project_id=project_id,
+        history_id=history_id,
+        prompt_id=prompt_id,
+        stage=trace['stage'],
+        provider=trace.get('provider') or 'unknown',
+        model=trace.get('model') or 'unknown',
+        system_prompt=trace.get('system_prompt') or '',
+        user_prompt=trace.get('user_prompt') or '',
+        assistant_response=trace.get('assistant_response') or '',
+        raw_response=trace.get('raw_response'),
+        fallback_used=trace.get('fallback_used', False),
+    )
+
+
+def _persist_failed_freeform_llm_traces(manager: DatabaseManager, *, request: FreeformSoftwareRequest, error: RequestInterpretationError) -> None:
+    """Persist failed interpretation traces under an unassigned bucket for dashboard inspection."""
+    trace = error.trace if isinstance(error.trace, dict) else {}
+    if not trace:
+        return
+    base_trace = dict(trace)
+    base_trace['raw_response'] = {
+        'failure_message': str(error),
+        'source': {'type': request.source, 'chat_id': request.chat_id, 'chat_type': request.chat_type},
+        'provider_trace': trace.get('raw_response'),
+    }
+    _persist_llm_trace(manager, project_id=UNASSIGNED_LLM_TRACE_PROJECT_ID, trace=base_trace)
+    naming_trace = trace.get('project_naming') if isinstance(trace.get('project_naming'), dict) else None
+    if naming_trace:
+        enriched_naming_trace = dict(naming_trace)
+        enriched_naming_trace['raw_response'] = {
+            'failure_message': str(error),
+            'source': {'type': request.source, 'chat_id': request.chat_id, 'chat_type': request.chat_type},
+            'provider_trace': naming_trace.get('raw_response'),
+        }
+        _persist_llm_trace(manager, project_id=UNASSIGNED_LLM_TRACE_PROJECT_ID, trace=enriched_naming_trace)
+
+
 async def _run_freeform_generation(
     request: FreeformSoftwareRequest,
     db: Session,
@@ -576,33 +746,21 @@ async def _run_freeform_generation(
             manager = DatabaseManager(db)
             prompts = manager.get_prompt_events(project_id=project_data.get('project_id'))
             prompt_id = prompts[0]['id'] if prompts else None
-            manager.log_llm_trace(
+            _persist_llm_trace(
+                manager,
                 project_id=project_data.get('project_id'),
                 history_id=project_data.get('history_id'),
                 prompt_id=prompt_id,
-                stage=interpretation_trace['stage'],
+                trace=interpretation_trace,
-                provider=interpretation_trace['provider'],
-                model=interpretation_trace['model'],
-                system_prompt=interpretation_trace['system_prompt'],
-                user_prompt=interpretation_trace['user_prompt'],
-                assistant_response=interpretation_trace['assistant_response'],
-                raw_response=interpretation_trace.get('raw_response'),
-                fallback_used=interpretation_trace.get('fallback_used', False),
             )
             naming_trace = interpretation_trace.get('project_naming')
             if naming_trace:
-                manager.log_llm_trace(
+                _persist_llm_trace(
+                    manager,
                     project_id=project_data.get('project_id'),
                     history_id=project_data.get('history_id'),
                     prompt_id=prompt_id,
-                    stage=naming_trace['stage'],
+                    trace=naming_trace,
-                    provider=naming_trace['provider'],
-                    model=naming_trace['model'],
-                    system_prompt=naming_trace['system_prompt'],
-                    user_prompt=naming_trace['user_prompt'],
-                    assistant_response=naming_trace['assistant_response'],
-                    raw_response=naming_trace.get('raw_response'),
-                    fallback_used=naming_trace.get('fallback_used', False),
                 )
         response['interpreted_request'] = structured_request.model_dump()
         response['routing'] = routing
@@ -622,6 +780,11 @@ async def _run_freeform_generation(
                 },
             )
         return response
+    except RequestInterpretationError as exc:
+        _persist_failed_freeform_llm_traces(manager, request=request, error=exc)
+        if queue_item_id is not None:
+            DatabaseManager(db).fail_queued_prompt(queue_item_id, str(exc))
+        raise
     except Exception as exc:
         if queue_item_id is not None:
             DatabaseManager(db).fail_queued_prompt(queue_item_id, str(exc))
@@ -664,6 +827,7 @@ async def _process_prompt_queue_batch(limit: int = 1, force: bool = False) -> di
                 process_now=True,
             )
             response = await _run_freeform_generation(request, work_db, queue_item_id=claimed['id'])
+            await _notify_telegram_queue_result(request, response=response)
             processed.append(
                 {
                     'queue_item_id': claimed['id'],
@@ -673,6 +837,7 @@ async def _process_prompt_queue_batch(limit: int = 1, force: bool = False) -> di
             )
         except Exception as exc:
             DatabaseManager(work_db).fail_queued_prompt(claimed['id'], str(exc))
+            await _notify_telegram_queue_result(request, error_message=str(exc))
             processed.append({'queue_item_id': claimed['id'], 'status': 'failed', 'error': str(exc)})
         finally:
             work_db.close()
@@ -788,6 +953,7 @@ def health_check():
         'database_target': runtime['target'],
         'database_name': runtime['database'],
         'integrations': {
+            'ollama': _get_ollama_health(),
             'gitea': _get_gitea_health(),
             'home_assistant': _get_home_assistant_health(),
         },
@@ -861,7 +1027,15 @@ def reset_runtime_setting(setting_key: str, db: DbSession):
 @app.post('/generate')
 async def generate_software(request: SoftwareRequest, db: DbSession):
     """Create and record a software-generation request."""
-    return await _run_generation(request, db)
+    try:
+        return await _run_generation(request, db)
+    except Exception as exc:
+        DatabaseManager(db).log_system_event(
+            component='api',
+            level='ERROR',
+            message=f"Structured generation failed: {exc}",
+        )
+        return _generation_error_payload(message=str(exc), request=request)
 
 
 @app.post('/generate/text')
@@ -883,7 +1057,7 @@ async def generate_software_from_text(request: FreeformSoftwareRequest, db: DbSe
             },
         }
 
-    if request.source == 'telegram' and database_module.settings.prompt_queue_enabled and not request.process_now:
+    if _should_queue_telegram_request(request):
         manager = DatabaseManager(db)
         queue_item = manager.enqueue_prompt(
             prompt_text=request.prompt_text,
@@ -892,12 +1066,19 @@ async def generate_software_from_text(request: FreeformSoftwareRequest, db: DbSe
             chat_type=request.chat_type,
             source_context={'chat_id': request.chat_id, 'chat_type': request.chat_type},
         )
+        queue_gate = await _get_queue_gate_status(force=False)
+        if not database_module.settings.prompt_queue_enabled or database_module.settings.prompt_queue_auto_process:
+            _schedule_prompt_queue_processing()
         return {
             'status': 'queued',
-            'message': 'Prompt queued for energy-aware processing.',
+            'message': (
+                'Prompt accepted for background processing.'
+                if not database_module.settings.prompt_queue_enabled else
+                'Prompt queued for background processing.'
+            ),
             'queue_item': queue_item,
             'queue_summary': manager.get_prompt_queue_summary(),
-            'queue_gate': await _get_queue_gate_status(force=False),
+            'queue_gate': queue_gate,
             'source': {
                 'type': request.source,
                 'chat_id': request.chat_id,
@@ -905,7 +1086,22 @@ async def generate_software_from_text(request: FreeformSoftwareRequest, db: DbSe
             },
         }
 
-    return await _run_freeform_generation(request, db)
+    try:
+        return await _run_freeform_generation(request, db)
+    except Exception as exc:
+        DatabaseManager(db).log_system_event(
+            component='api',
+            level='ERROR',
+            message=f"Free-form generation failed for source={request.source}: {exc}",
+        )
+        return _generation_error_payload(
+            message=str(exc),
+            source={
+                'type': request.source,
+                'chat_id': request.chat_id,
+                'chat_type': request.chat_type,
+            },
+        )
 
 
 @app.get('/queue')