Add retry logic to ClickUp API writes and fix review status

- Add _retry() helper to ClickUpClient (3 attempts, exponential backoff,
  only retries 5xx/transport errors)
- Apply retry to update_task_status, add_comment, upload_attachment
- Fix review_status from "review" to "internal review" in config and defaults
- Update SOUL.md personality and USER.md profile

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

cheddahbot/clickup.py

@@ -3,6 +3,7 @@
 from __future__ import annotations
 
 import logging
+import time
 from dataclasses import dataclass, field
 from pathlib import Path
 from typing import Any
@@ -144,30 +145,58 @@ class ClickUpClient:
         log.info("Found %d tasks across %d lists in space %s", len(all_tasks), len(list_ids), space_id)
         return all_tasks
 
-    # ── Write ──
+    # ── Write (with retry) ──
+
+    @staticmethod
+    def _retry(fn, max_attempts: int = 3, backoff: float = 2.0):
+        """Call *fn* up to *max_attempts* times with exponential backoff.
+
+        Returns the result of *fn* on success, or re-raises the last exception.
+        Only retries on network/transport errors and 5xx status errors.
+        """
+        last_exc: Exception | None = None
+        for attempt in range(1, max_attempts + 1):
+            try:
+                return fn()
+            except (httpx.TransportError, httpx.HTTPStatusError) as e:
+                # Don't retry 4xx client errors (bad request, auth, not found, etc.)
+                if isinstance(e, httpx.HTTPStatusError) and e.response.status_code < 500:
+                    raise
+                last_exc = e
+                if attempt < max_attempts:
+                    wait = backoff ** attempt
+                    log.warning("Retry %d/%d after %.1fs: %s", attempt, max_attempts, wait, e)
+                    time.sleep(wait)
+        raise last_exc
 
     def update_task_status(self, task_id: str, status: str) -> bool:
         """Update a task's status."""
         try:
+            def _call():
                 resp = self._client.put(f"/task/{task_id}", json={"status": status})
                 resp.raise_for_status()
+                return resp
+            self._retry(_call)
             log.info("Updated task %s status to '%s'", task_id, status)
             return True
-        except httpx.HTTPStatusError as e:
+        except (httpx.TransportError, httpx.HTTPStatusError) as e:
             log.error("Failed to update task %s status: %s", task_id, e)
             return False
 
     def add_comment(self, task_id: str, text: str) -> bool:
         """Add a comment to a task."""
         try:
+            def _call():
                 resp = self._client.post(
                     f"/task/{task_id}/comment",
                     json={"comment_text": text},
                 )
                 resp.raise_for_status()
+                return resp
+            self._retry(_call)
             log.info("Added comment to task %s", task_id)
             return True
-        except httpx.HTTPStatusError as e:
+        except (httpx.TransportError, httpx.HTTPStatusError) as e:
             log.error("Failed to add comment to task %s: %s", task_id, e)
             return False
 
@@ -183,6 +212,7 @@ class ClickUpClient:
             log.warning("Attachment file not found: %s", fp)
             return False
         try:
+            def _call():
                 with open(fp, "rb") as f:
                     resp = httpx.post(
                         f"{BASE_URL}/task/{task_id}/attachment",
@@ -191,9 +221,11 @@ class ClickUpClient:
                         timeout=60.0,
                     )
                 resp.raise_for_status()
+                return resp
+            self._retry(_call)
             log.info("Uploaded attachment %s to task %s", fp.name, task_id)
             return True
-        except httpx.HTTPStatusError as e:
+        except (httpx.TransportError, httpx.HTTPStatusError) as e:
             log.warning("Failed to upload attachment to task %s: %s", task_id, e)
             return False
 

cheddahbot/config.py

@@ -40,7 +40,7 @@ class ClickUpConfig:
     space_id: str = ""
     poll_interval_minutes: int = 20
     poll_statuses: list[str] = field(default_factory=lambda: ["to do"])
-    review_status: str = "review"
+    review_status: str = "internal review"
     in_progress_status: str = "in progress"
     task_type_field_name: str = "Work Category"
     default_auto_execute: bool = False

config.yaml

@@ -43,7 +43,7 @@ email:
 clickup:
   poll_interval_minutes: 20       # 3x per hour
   poll_statuses: ["to do"]
-  review_status: "review"
+  review_status: "internal review"
   in_progress_status: "in progress"
   task_type_field_name: "Work Category"
   default_auto_execute: false

identity/SOUL.md

@@ -1,11 +1,12 @@
 # Soul
 
-You are Cheddah, a sharp and resourceful AI assistant.
+You are Cheddah, a sharp and resourceful AI assistant.  You are built on the avatar of Winston Churchill.  Smart, confident, but friendly.
 
 ## Personality
 - Direct, no-nonsense, but warm
 - You use humor when appropriate
-- You're proactive - suggest things before being asked
+- You're proactive - suggest things before being asked.  Especially as you begin to notice patterns in my behavior and schedule you can recommend items that fit.
+- You are a good designer (css/html/js) and Bryan is not so you should help him when you can.  If we don't have a designer skill installed you should go find a few and recommend one or two to include that you can use.
 - You remember what the user tells you and reference it naturally
 - You adapt your communication style to match the user's preferences
 
@@ -16,5 +17,6 @@ You are Cheddah, a sharp and resourceful AI assistant.
 - Ask for clarification rather than guessing on important decisions
 
 ## Quirks
-- You occasionally use the word "cheddah" as slang for money/value
+- You like to open converstions with random trivia facts - but only once at the begining per chat.
+- You may use puns or quotes from Winston Churchill that fit the situation - but not too forced.
 - You appreciate efficiency and elegant solutions

identity/USER.md

@@ -1,16 +1,19 @@
 # User Profile
 
 ## Identity
-- Name: (your name here)
+- Name: Bryan
-- How to address: (first name, nickname, etc.)
+- How to address: Bryan or Yan
 - Origin: Cheddah is named after the user's Xbox Live gamertag, "CheddahYetti."
 - Fun Fact: The name is a nod to living in Wisconsin and the user being a "big guy."
 
 ## Context
-- Technical level: (beginner/intermediate/advanced)
+- Technical level: (advanced in Python)
 - Primary language: Python
 - Working on: (current projects)
 
+
 ## Preferences
-- Communication style: (concise/detailed)
+- Communication style: Likes to know what is going on before giving the go-ahead, but once he understands is willing to let the agents go to work without any input.
-- (anything else you want the agent to know)
+- If he says he is going to bed or going away for awhile, you can ask if we can run in unattended mode - he'll usually say yes.
+- Simple code is better - he's the only guy in the shop so dont do code like it's for an enterprise.  Simple and maintainable is important.
+- He needs help with organization, and he really needs help keeping project documentation up to date.  Do that for him.