Your Drime folders show up in Finder as usual. Then sync stops, a Sign In button replaces your files, and signing in again fixes things only until the next time. At least one Mac user has reported exactly this with Drime on macOS 27. The original walkthrough comes from MacHabits.
The scary question is whether your files are gone. Most likely they aren’t. What sits on your Mac right now, though, depends on whether each file was online only or available offline. Before you touch the sign-in loop, find out which files you really have locally and protect them.
Online only vs available offline
Drime, like Dropbox or OneDrive, can list every file in Finder without keeping all of them on your Mac:
- Online only: Finder lists the file, but your Mac holds just a placeholder. The content downloads when you open it, which takes a connection and a working sign-in.
- Available offline: the whole file sits on your Mac’s disk and opens without a connection.
While the app is signed out, online-only files can’t be opened from the Mac, yet they remain safe in your Drime account. Files you marked available offline should still be on your disk.
First, check your files in the browser
Sign in to Drime in a web browser and open the folders that matter to you. If the files are there, nothing was deleted, and the fault lies only in the link between your Mac and your account. That removes the urgency from everything below.
See what is actually stored on your Mac
- Look at the icons. A cloud icon beside a file in Finder usually means online only. No cloud icon means the file is stored locally.
- Use Get Info. Select a file and press Command-I, then compare the file’s size with its size on disk. A placeholder takes little or no disk space; a local file takes about its full size.
- Check the folder size. Select the entire Drime folder and open Get Info. A few megabytes for a folder that holds gigabytes online tells you almost everything is online only.
If Drime appears under Locations in Finder’s sidebar, it uses the cloud storage integration built into macOS, and its local files live in ~/Library/CloudStorage. Don’t move or rename anything in that folder by hand.
Protect your offline files before fixing anything
Some fixes, such as signing out, removing the Drime location or reinstalling the app, can delete the local copies. Before you try any of them:
- Copy the files you need offline to a normal folder such as Documents or an external drive, especially anything you edited while sync was stopped.
- Make sure your Time Machine backup is up to date.
Edits made while sync is stopped exist only on your Mac until Drime uploads them. Those files are the most at risk.
Fix the sign-in loop
- Update the Drime desktop app. After a major macOS release, sync apps often need an update to cope with changes in Finder. Check Drime’s download page or the app’s own update option.
- Check that the extension is allowed. Open System Settings > General > Login Items & Extensions and look for Drime under File Providers or Extensions. It should be switched on, and Drime should be allowed under Login Items so it launches with your Mac.
- Sign in from the app, not from Finder. Quit Drime completely, reopen it from Applications, and sign in through the app’s own window or menu bar icon.
- Check the date and time. Sign-in tokens fail when the Mac’s clock is wrong. In General > Date & Time, make sure the time is set automatically.
- Restart the Mac once after updating Drime so macOS reloads the sync extension.
For the original version of these steps, see the MacHabits guide to the Finder sign-in loop.
If it keeps happening
Contact Drime support with your macOS version, the Drime app version, what you see in Finder and roughly how long you stay signed in. If you depend on offline access for work or travel, keep a copy of essential files outside the sync folder until a fix is confirmed.
The short version
A Sign In prompt in Finder doesn’t by itself mean Drime deleted your files. Check them in the web app, then use Finder’s icons and Get Info to see what is really stored on your Mac. Copy anything important out of the sync folder before signing out or reinstalling. After that, update Drime, confirm its extension is enabled in Login Items & Extensions, and sign in from the app itself.
More on the Finder prompt: Finder says Sign In again on MacHabits.
Source: https://machabits.info/articles/finder-says-sign-in-again