Failing task generation | API: Headers Timeout Erro within generateObject

[bitflorist]

Description

The task generation feature in Taskmaster-AI is failing to complete and times out when attempting to parse PRD files and generate tasks. The process starts but eventually fails with a "Headers Timeout Error" from the Anthropic API connection.
(Google API works, doesn't implicate local issue)

Steps to Reproduce

1. Create or use an existing PRD file at concept/PRD.txt
2. Attempt to generate 10 tasks using the command (likely something like taskmaster generate or similar)
3. Wait for the process to execute

Expected Behavior

The system should successfully parse the PRD file and generate 10 tasks as requested, completing the operation within a reasonable timeframe.

Actual Behavior

The operation begins executing (showing the loading spinner) but eventually fails with an error: "Cannot connect to API: Headers Timeout Error" after multiple retry attempts. The log shows it's trying to call the Anthropic API (claude-3-7-sonnet-20250219) but cannot establish a successful connection.

Screenshots or Logs

[INFO] Parsing PRD file: concept/PRD.txt, Force: false, Append: false
[INFO] Reading PRD content from concept/PRD.txt
[INFO] Calling AI service to generate tasks from PRD...
[INFO] generateObjectService called {"role":"main"}
[INFO] New AI service call with role: main
[INFO] Attempt 1/3 calling generateAnthropicObject (Provider: anthropic, Model: claude-3-7-sonnet-20250219, Role: main)
[ERROR] Anthropic generateObject ('tasks_data') failed: Failed after 4 attempts. Last error: Cannot connect to API: Headers Timeout Error
[WARN] Attempt 1 failed for role main (generateAnthropicObject / anthropic): Failed after 4 attempts. Last error: Cannot connect to API: Headers Timeout Error
[INFO] Retryable error detected. Retrying in.1s...
[INFO] Attempt 2/3 calling generateAnthropicObject (Provider: anthropic, Model: claude-3-7-sonnet-20250219, Role: main)

Environment

• Task Master version: 0.13.2
• Node.js version: v23.11.0
• Operating system: OSX
• IDE (if applicable): ghostly CLI, Cursor Terminal, Warp

Additional Context

The error occurs during the API call to Anthropic's Claude 3.7 Sonnet model. The system is making multiple attempts (showing retry logic) but consistently fails with a "Headers Timeout Error" which suggests either network connectivity issues, firewall restrictions, API rate limiting, or possibly an issue with the Anthropic API itself. The error occurs specifically during the task generation phase when parsing the PRD and attempting to use the AI service to generate tasks.

[eyaltoledano]

Headers timeout would be happening either if the endpoint is overloaded or if your authentication is not working — double check the API is valid, billing is good to go and that Claude isn’t down

Is your fallback working?

[ThomasClague]

Also getting this problem parsing through the CLI for a larger task number (16) however works with task number 1

I can see the logs in anthropics dashboard showing error code 499 client disconnected

[AIFlowML]

The task are generated with success but it stay there a lot thinking and at at point it fail. 20 steps.

Strange that is all there but it still cannot find it in the folder.
Im on OSX.

[Crunchyman-ralph]

Seems like we're unable to reproduce, moving this to discussions, feel free to close if this issue persists