Docs / Troubleshooting / Cloud sync

Troubleshooting

Cloud sync is not just “internet up or down.”

Contextify sync talks to one configured target: hosted Contextify Cloud or your self-hosted server. If that target is unreachable, the app can be offline even while other websites work.

Status states

Status Meaning What to do
Healthy Cloud is up to date for the latest checked state. No action needed.
Syncing Contextify is uploading recent changes or downloading remote changes. Let it finish. Large catch-up syncs can take time after local ingestion is done.
Waiting Transcript ingestion needs to finish before sync starts. Wait for local indexing to settle. See Ingestion and syncing.
Deferred Sync is paused while transcript ingestion is active. It retries automatically, or you can sync manually later.
Offline The configured cloud target could not be reached. Check the target URL, DNS, VPN, and server health.
Attention needed or Error The latest sync attempt failed or progress needs review. Use Retry and Copy Diagnostics from Settings → Cloud.

Start in Settings → Cloud

  1. Read the latest error

    The error box shows the latest local or server sync failure. It also shows the configured target and when the status was last checked.

  2. Click Retry

    Retry reloads the saved cloud configuration, triggers sync, refreshes status, and refreshes account details.

  3. Copy diagnostics

    Copy Diagnostics includes provider, server, device name, status, last checked time, and sanitized status/account errors.

Hosted Cloud checks

Hosted Cloud uses cloud.contextify.sh. If other websites work but hosted Cloud does not, avoid telling yourself “the internet is down.” Check the specific target. 

curl -i https://cloud.contextify.sh/api/v1/health
contextify cloud status --json

DNS failures for hosted Cloud may resolve on retry. Persistent failures usually point to local DNS settings, a blocked network, or a service incident.

Self-hosted checks

Self-hosted sync depends on the exact saved server URL. Check the scheme, hostname, port, VPN, and TLS certificate name. 

curl -i https://your-server.example.com/api/v1/health
contextify cloud status --json
contextify cloud sync --json

For Tailscale .ts.net servers, a DNS failure often means MagicDNS resolver state is broken on macOS. Reconnecting Tailscale or resetting its VPN configuration may be required.

Read the TLS, VPN, and Tailscale guide

When support can help fastest

Copy Diagnostics is designed to omit secrets, but still review it before sending. Include the diagnostics, the server URL with secrets removed, whether the target is hosted or self-hosted, and whether curl can reach /api/v1/health.

Also mention whether the Mac was still indexing or processing a large local history when the sync issue appeared.

Do not send raw API keys, browser cookies, magic links, OTP codes, or setup tokens.

Last updated: May 6, 2026