Cloud Sync Is Stuck

You opened Settings and one of your cloud backups (Drive, Dropbox, or OneDrive) has been showing 'Syncing...' for hours. Or you uploaded a document yesterday and it still is not in the cloud folder where it should be. Or you connected Dropbox and Colby connected Dropbox and now you are not sure whose folder anything is going to. That is what this article is about.

Cloud sync runs through a background queue. A worker picks documents off the queue and pushes them to your connected provider every minute or two. When a job hits a permanent failure (the source file got deleted from storage, an OAuth token was revoked, the provider returned a hard 4xx, the file exceeds a hard size limit), the old queue would retry it forever and block everyone behind it. The current version detects terminal failures, records them in a separate table, and moves on. Dropbox is now scoped to the workspace owner so staff and owner connections cannot collide.

The walkthrough below helps you figure out which kind of stuck you are hitting and what to do next. Most issues clear in 10 to 15 minutes once you fix the underlying cause (reconnect the integration, free up quota, etc.). If you have waited more than an hour with nothing moving, do not keep retrying. Message support and we can look at the queue directly and tell you in about 60 seconds whether the job is genuinely stuck or whether you are reading the wrong status.

Cloud sync runs in the background. When it stops moving, the cause is almost always one of: the integration disconnected, the source file no longer exists, or a job ahead of yours had so many failures it was clogging the queue. We fixed the third one recently, but it is still good to know how to spot.

Diagnostic decision tree

About terminal failures

Some sync failures are permanent and retrying will never help. If the original file was deleted from AwardLettr storage (because you deleted the document), no amount of retrying will sync it. The same is true if the recipient cloud account was deleted, or the file exceeds the provider's hard size limit.

We now track these as 'terminal failures' in a separate table. Jobs that hit a terminal failure stop retrying immediately — they do not clog the queue for other users. Jobs that hit 25+ retry failures, or run for 24+ hours with zero successful syncs, are also force-failed automatically.

Forcing a resync

If a document failed to sync and you have fixed the underlying cause (reconnected the integration, increased quota, etc.), you can force a resync from the document detail dialog on the appraisal. Look for the Retry Sync button. It puts the document back into the queue at the bottom.