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Upload times out with large session backlog, no batching/recovery #13

Description

@digitaljavelina

Description

When a large number of sessions accumulate locally (e.g. due to an initial timeout or temporary connectivity issue), all subsequent upload attempts fail with a timeout error. This creates a death spiral where the backlog grows with each failed attempt, making future uploads even less likely to succeed.

Environment

  • CLI version: 0.8.6
  • OS: macOS (Darwin 25.3.0)
  • Last successful upload: 2026-02-07
  • Sessions accumulating: ~2,500+ (filtered as <4min), with hundreds of longer sessions in the payload

Symptoms

Every hook-triggered and manual send command fails with:

[ERROR] Upload sessions: Request timed out. Your connection might be slow or the server is not responding
[ERROR] Failed to execute hook send

The server itself is reachable (responds in ~85ms to a basic HTTPS request), so it's the upload payload size/duration that exceeds the timeout, not a connectivity issue.

Secondary issue: timed-out uploads hold the execution lock, causing subsequent hook invocations to fail with:

Error: Another hook execution is already in progress

Reproduction

  1. Accumulate a few weeks of Claude Code sessions (~2,500+)
  2. Run npx vibe-log-cli send --silent --background --hook-trigger=sessionstart --hook-version=1.0.0 --all
  3. Upload starts, filters short sessions, then times out before completing

Expected behavior

Uploads should succeed regardless of backlog size, ideally by:

  • Batching large uploads into smaller chunks (e.g. 50-100 sessions per request)
  • Incremental sync — upload newest sessions first, then backfill older ones
  • A --limit or --since flag to allow partial uploads
  • Graceful recovery so one timeout doesn't permanently block future syncs

Logs

From ~/.vibe-log/upload.log (pattern repeating since early March):

=== Upload started at 2026-03-16T16:37:49.178Z ===
[INFO] Filtered out 2553 session(s) shorter than 4 minutes
[ERROR] Failed to upload sessions
[ERROR] Failed to execute hook send

From ~/.vibe-log/hooks.log:

VibelogError: Request timed out. Your connection might be slow or the server is not responding

Workaround attempted

Running the interactive npx vibe-log-cli menu and selecting manual sync updated lastSync in config.json, but upload.log shows no actual successful upload — the backlogged sessions remain unsynced.

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