Add "automation underway" and "error" ClickUp statuses for bot visibility

Tasks now show "automation underway" when the bot picks them up and "error"
on failure, replacing the old "in progress" / "to do" fallbacks that were
invisible on Bryan's ClickUp board. Folder watcher also syncs ClickUp status
on match, missing IMSURL, pipeline failure, success, and exceptions.

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

cheddahbot/config.py

@@ -44,6 +44,8 @@ class ClickUpConfig:
     poll_statuses: list[str] = field(default_factory=lambda: ["to do"])
     review_status: str = "internal review"
     in_progress_status: str = "in progress"
+    automation_status: str = "automation underway"
+    error_status: str = "error"
     task_type_field_name: str = "Work Category"
     default_auto_execute: bool = False
     skill_map: dict = field(default_factory=dict)

cheddahbot/scheduler.py

@@ -339,8 +339,8 @@ class Scheduler:
             "custom_fields": task.custom_fields,
         }
 
-        # Move to "in progress" on ClickUp immediately
+        # Move to "automation underway" on ClickUp immediately
-        client.update_task_status(task_id, self.config.clickup.in_progress_status)
+        client.update_task_status(task_id, self.config.clickup.automation_status)
         self.db.kv_set(kv_key, json.dumps(state))
 
         log.info("Executing ClickUp task: %s → %s", task.name, tool_name)
@@ -371,8 +371,8 @@ class Scheduler:
                     task_id,
                     f"⚠️ CheddahBot could not execute this task.\n\n{result[:2000]}",
                 )
-                # Move back to "to do" so it can be retried
+                # Move to "error" so Bryan can see what happened
-                client.update_task_status(task_id, "to do")
+                client.update_task_status(task_id, self.config.clickup.error_status)
 
                 self._notify(
                     f"ClickUp task skipped: **{task.name}**\n"
@@ -428,8 +428,8 @@ class Scheduler:
             client.add_comment(
                 task_id, f"❌ CheddahBot failed to complete this task.\n\nError: {str(e)[:2000]}"
             )
-            # Move back to "to do" so it can be retried after reset
+            # Move to "error" so Bryan can see what happened
-            client.update_task_status(task_id, "to do")
+            client.update_task_status(task_id, self.config.clickup.error_status)
 
             self._notify(
                 f"ClickUp task failed: **{task.name}**\n"
@@ -547,6 +547,11 @@ class Scheduler:
         # Extract tool args from matched task
         task_id = matched_task.id
         log.info("Matched '%s' to ClickUp task %s (%s)", filename, task_id, matched_task.name)
+
+        # Set ClickUp status to "automation underway"
+        client = self._get_clickup_client()
+        client.update_task_status(task_id, self.config.clickup.automation_status)
+
         self._notify(
             f"Folder watcher: matched **{filename}** to ClickUp task **{matched_task.name}**.\n"
             f"Starting Cora Backlinks pipeline...",
@@ -570,6 +575,8 @@ class Scheduler:
                     }
                 ),
             )
+            # Set ClickUp status to "error" so it's visible on the board
+            client.update_task_status(task_id, self.config.clickup.error_status)
             self._notify(
                 f"Folder watcher: **{filename}** matched task **{matched_task.name}** "
                 f"but **IMSURL is empty**. Set the IMSURL field in ClickUp before "
@@ -614,6 +621,7 @@ class Scheduler:
                         }
                     ),
                 )
+                client.update_task_status(task_id, self.config.clickup.error_status)
                 self._notify(
                     f"Folder watcher: pipeline **failed** for **{filename}**.\n"
                     f"Error: {result[:200]}",
@@ -641,6 +649,7 @@ class Scheduler:
                         }
                     ),
                 )
+                client.update_task_status(task_id, self.config.clickup.review_status)
                 self._notify(
                     f"Folder watcher: pipeline **completed** for **{filename}**.\n"
                     f"ClickUp task: {matched_task.name}",
@@ -661,6 +670,7 @@ class Scheduler:
                     }
                 ),
             )
+            client.update_task_status(task_id, self.config.clickup.error_status)
 
     def _match_xlsx_to_clickup(self, normalized_stem: str):
         """Find a ClickUp Link Building task whose Keyword matches the file stem.

cheddahbot/tools/linkbuilding.py

@@ -275,11 +275,11 @@ def _find_clickup_task(ctx: dict, keyword: str) -> str:
             if db:
                 db.kv_set(f"clickup:task:{task_id}:state", json.dumps(state))
 
-            # Move to "in progress"
+            # Move to "automation underway"
             cu_client2 = _get_clickup_client(ctx)
             if cu_client2:
                 try:
-                    cu_client2.update_task_status(task_id, config.clickup.in_progress_status)
+                    cu_client2.update_task_status(task_id, config.clickup.automation_status)
                 except Exception as e:
                     log.warning("Failed to update ClickUp status for %s: %s", task_id, e)
                 finally:
@@ -361,9 +361,7 @@ def _fail_clickup_task(ctx: dict | None, task_id: str, error_msg: str) -> None:
         return
 
     config = ctx.get("config")
-    skill_map = config.clickup.skill_map if config else {}
+    error_status = config.clickup.error_status if config else "error"
-    lb_map = skill_map.get("Link Building", {})
-    error_status = lb_map.get("error_status", "internal review")
 
     db = ctx.get("db")
     if db:

cheddahbot/tools/press_release.py

@@ -116,11 +116,11 @@ def _find_clickup_task(ctx: dict, company_name: str) -> str:
         if db:
             db.kv_set(f"clickup:task:{task_id}:state", json.dumps(state))
 
-        # Move to "in progress" on ClickUp
+        # Move to "automation underway" on ClickUp
         cu_client2 = _get_clickup_client(ctx)
         if cu_client2:
             try:
-                cu_client2.update_task_status(task_id, config.clickup.in_progress_status)
+                cu_client2.update_task_status(task_id, config.clickup.automation_status)
             except Exception as e:
                 log.warning("Failed to update ClickUp status for %s: %s", task_id, e)
             finally:
@@ -516,13 +516,13 @@ def write_press_releases(
         if cu_client:
             try:
                 config = ctx["config"]
-                cu_client.update_task_status(clickup_task_id, config.clickup.in_progress_status)
+                cu_client.update_task_status(clickup_task_id, config.clickup.automation_status)
                 cu_client.add_comment(
                     clickup_task_id,
                     f"🔄 CheddahBot starting press release creation.\n\n"
                     f"Topic: {topic}\nCompany: {company_name}",
                 )
-                log.info("ClickUp task %s set to in-progress", clickup_task_id)
+                log.info("ClickUp task %s set to automation-underway", clickup_task_id)
             except Exception as e:
                 log.warning("ClickUp start-sync failed for %s: %s", clickup_task_id, e)
 

config.yaml

@@ -45,6 +45,8 @@ clickup:
   poll_statuses: ["to do"]
   review_status: "internal review"
   in_progress_status: "in progress"
+  automation_status: "automation underway"
+  error_status: "error"
   task_type_field_name: "Work Category"
   default_auto_execute: false
   skill_map:
@@ -60,7 +62,7 @@ clickup:
       tool: "run_link_building"
       auto_execute: false
       complete_status: "complete"
-      error_status: "internal review"
+      error_status: "error"
       field_mapping:
         lb_method: "LB Method"
         project_name: "task_name"

tests/test_scheduler.py

@@ -32,6 +32,8 @@ class _FakeClickUpConfig:
     poll_statuses: list[str] = field(default_factory=lambda: ["to do"])
     review_status: str = "internal review"
     in_progress_status: str = "in progress"
+    automation_status: str = "automation underway"
+    error_status: str = "error"
     task_type_field_name: str = "Work Category"
     default_auto_execute: bool = True
     skill_map: dict = field(default_factory=lambda: {"Press Release": _PR_MAPPING})
@@ -220,7 +222,7 @@ class TestExecuteTask:
 
         mock_client.update_task_status.assert_any_call(
             "t1",
-            "in progress",
+            "automation underway",
         )
 
         raw = tmp_db.kv_get("clickup:task:t1:state")
@@ -266,7 +268,7 @@ class TestExecuteTask:
         assert "output/pr.docx" in state["deliverable_paths"]
 
     def test_failure_flow(self, tmp_db):
-        """Failed: state=failed, error comment, back to 'to do'."""
+        """Failed: state=failed, error comment, status set to 'error'."""
         config = _FakeConfig()
         agent = MagicMock()
         agent._tools = MagicMock()
@@ -288,7 +290,7 @@ class TestExecuteTask:
         )
         scheduler._execute_task(task)
 
-        mock_client.update_task_status.assert_any_call("t1", "to do")
+        mock_client.update_task_status.assert_any_call("t1", "error")
         mock_client.add_comment.assert_called_once()
         comment_text = mock_client.add_comment.call_args[0][1]
         assert "failed" in comment_text.lower()