srbhr/Resume-Matcher · error · HTTPException

Failed to generate outreach message. Please try again.

Error message

Failed to generate outreach message. Please try again.

What it means

This 500 is raised by generate_outreach_endpoint when generate_outreach_message() throws any exception. The endpoint catches it, logs 'Outreach message generation failed', and returns a generic client-safe message while preserving the real cause in server logs.

Source

Thrown at apps/backend/app/routers/resumes.py:1898

    # Get resume data
    resume_data = resume.get("processed_data")
    if not resume_data:
        raise HTTPException(
            status_code=400,
            detail="Resume has no processed data. Please re-upload the resume.",
        )

    # Get language setting
    language = get_content_language()

    # Generate outreach message
    try:
        outreach_content = await generate_outreach_message(
            resume_data, job["content"], language
        )
    except Exception as e:
        logger.error(f"Outreach message generation failed: {e}")
        raise HTTPException(
            status_code=500,
            detail="Failed to generate outreach message. Please try again.",
        )

    # Save to resume record
    await db.update_resume(resume_id, {"outreach_message": outreach_content})

    return GenerateContentResponse(
        content=outreach_content,
        message="Outreach message generated successfully",
    )


@router.post(
    "/{resume_id}/generate-interview-prep",
    response_model=GenerateInterviewPrepResponse,
)
async def generate_interview_prep_endpoint(

View on GitHub (pinned to 116f9cc3b0)

Solutions

1. Check backend logs for 'Outreach message generation failed: <e>' to find the root cause
2. Validate the LLM API key and account quota in the backend environment
3. Retry — transient provider errors often succeed on a second attempt
4. Trim or truncate the resume/job description if the payload is too large

Example fix

// before
await generateOutreach(tailoredResume.id); // 500 generic
// after
try {
  await generateOutreach(tailoredResume.id);
} catch (e) {
  // check server logs for the underlying AI error, then retry
}

const resume = await getResume(resumeId);
const improvement = await getImprovementByTailoredResume(resumeId);
if (!resume?.processedData || !improvement?.jobId) throw new Error('Invalid inputs for outreach generation');

try {
  await api.generateOutreach(resumeId);
} catch (e) {
  if (e.response?.status === 500) {
    // transient AI failure most likely: check server logs, then retry with backoff
    await sleep(2000);
    return api.generateOutreach(resumeId);
  }
  throw e;
}

When it happens

Trigger: POSTing to the outreach route with valid resume/job context, but the AI helper fails — LLM API timeout, rate limiting, invalid API key, or resume/job content the model cannot handle.

Common situations: Missing/expired LLM provider credentials, upstream provider outage or 429s, oversized combined resume+job-description payload, blocked network egress.

Related errors

• Failed to generate cover letter. Please try again.
• Resume not found: {resume_id}
• LLM completion failed. Please check your API configuration a
• JSON extraction exceeded max recursion depth: {_depth}
• Content too large for JSON extraction: {len(content)} bytes

AI-assisted analysis of srbhr/Resume-Matcher@116f9cc3b0 (2026-08-28). Data as JSON: /api/errors/7eaec78b18b28817. Report an issue: GitHub.