Increase CLI timeout to 15min, fix result file reprocessing, and save outlines directly

- Bump Claude Code subprocess timeout from 5 to 15 minutes for longer content tasks
- Fix scheduler result file loop: unlink source if already exists in processed/ dir
- Pass outline save path to execution brain so it writes directly to network share

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

cheddahbot/llm.py

@@ -218,10 +218,10 @@ class LLMAdapter:
             )
 
         try:
-            stdout, stderr = proc.communicate(input=prompt, timeout=300)
+            stdout, stderr = proc.communicate(input=prompt, timeout=900)
         except subprocess.TimeoutExpired:
             proc.kill()
-            return "Error: Claude Code execution timed out after 5 minutes."
+            return "Error: Claude Code execution timed out after 15 minutes."
 
         if proc.returncode != 0:
             return f"Execution error: {stderr or 'unknown error'}"

cheddahbot/scheduler.py

@@ -653,6 +653,9 @@ class Scheduler:
                 result_path.rename(processed_dir / result_path.name)
             except OSError as e:
                 log.warning("Could not move result file %s: %s", result_path.name, e)
+                # If it already exists in processed/, delete the source to stop reprocessing
+                if (processed_dir / result_path.name).exists():
+                    result_path.unlink(missing_ok=True)
 
     # ── Folder Watcher ──
 

cheddahbot/tools/content_creation.py

@@ -228,6 +228,7 @@ def _build_phase1_prompt(
     cora_path: str,
     capabilities_default: str,
     is_service_page: bool = False,
+    outline_save_path: str = "",
 ) -> str:
     """Build the Phase 1 prompt that triggers the content-researcher skill.
 
@@ -286,10 +287,19 @@ def _build_phase1_prompt(
             f'\nWhen asked about company capabilities, respond with: "{capabilities_default}"'
         )
 
-    parts.append(
+    if outline_save_path:
-        "\nDeliver the outline as a complete markdown document with sections, "
+        parts.append(
-        "headings, entity targets, and keyword placement notes."
+            f"\nSave the finished outline to `{outline_save_path}`. "
-    )
+            "Create any missing directories first. "
+            "The outline must be a complete markdown document with sections, "
+            "headings, entity targets, and keyword placement notes. "
+            "Do NOT save it anywhere else."
+        )
+    else:
+        parts.append(
+            "\nDeliver the outline as a complete markdown document with sections, "
+            "headings, entity targets, and keyword placement notes."
+        )
     return "\n".join(parts)
 
 
@@ -847,12 +857,29 @@ def _run_phase1(
     capabilities_default: str,
     is_service_page: bool = False,
 ) -> str:
+    # Compute the outline save path upfront so the execution brain writes
+    # directly to the network share (or local fallback).
+    slug = _slugify(keyword) or "unknown"
+    outline_path = ""
+    if config.content.outline_dir:
+        primary = Path(config.content.outline_dir) / slug
+        try:
+            primary.mkdir(parents=True, exist_ok=True)
+            outline_path = str(primary / "outline.md")
+        except OSError as e:
+            log.warning("Network path unavailable (%s), falling back to local: %s", primary, e)
+    if not outline_path:
+        local = _LOCAL_CONTENT_DIR / slug
+        local.mkdir(parents=True, exist_ok=True)
+        outline_path = str(local / "outline.md")
+
     # ClickUp: move to automation underway
     if task_id:
         _sync_clickup_start(ctx, task_id)
 
     prompt = _build_phase1_prompt(
-        url, keyword, content_type, cora_path, capabilities_default, is_service_page
+        url, keyword, content_type, cora_path, capabilities_default, is_service_page,
+        outline_save_path=outline_path,
     )
 
     log.info("Phase 1 — researching + outlining for '%s' (%s)", keyword, url or "new content")
@@ -874,8 +901,15 @@ def _run_phase1(
             _sync_clickup_fail(ctx, task_id, result)
         return result
 
-    # Save the outline
+    # Verify the outline was saved by the execution brain
-    outline_path = _save_content(result, keyword, "outline.md", config)
+    if not Path(outline_path).is_file():
+        log.warning(
+            "Execution brain did not save outline to %s; saving result text as fallback.",
+            outline_path,
+        )
+        Path(outline_path).parent.mkdir(parents=True, exist_ok=True)
+        Path(outline_path).write_text(result, encoding="utf-8")
+
     log.info("Outline saved to: %s", outline_path)
 
     # ClickUp: move to outline review + store OutlinePath