Dropbox delete all files in an externally synced, mac folder

I have just have had 3 scares in a row where Dropbox, in front om my eyes started to delete ALL 4000 files from a dropbox folder.
Just one dropboxfolder that happened to be external indexed by Devonthink.

You think that’s a coincidence?

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Yes, because it didn’t not happen to any other dropbox files. Only the one indexed by Devonthink on one machine.

Had you deleted any files in the database then emptied the database’s Trash?

Are (or were) the files always available locally on your Macs? And is the location in the filesystem (the Dropbox folder) always the same?

It happened for the 4th time, 4GB data deleted…

No files were deleted, just added.
The Dropbox folder is in the same position.

The file lost are ONLY the files (stored in dropboxfolder) that are indexed in one particular DevonThink Database that is synched using Dropbox.

Going through this whole thread I am unsure I have understood you correctly:

  • the folder you are indexing is on Dropbox?
  • at the same time, the database which contains the indexed folder is syncing to Dropbox?

That would seem to be a critical question which you (@anderswt) have not answered. Also: have you got enough space available on Dropbox?

Yes, I use 3.8 % of 2.0 TB.

I use dropbox to sync raw files in a sub-filestructure.

The Ive create a DevonThink Database that is also synched in Dropbox.
This DT database is not in the same filestructure as the raw files.

I then added to the DT an indexation of the raw files.

Also I noted that only a few few files were left after the deletion.

Until evidence to the contrary is available, I would assume that the most likely cause of the problem is that the indexed files are not available locally on the Mac at all times. Make sure the files are set to be available locally (see this entry in the Dropbox Community for guidance).


Thanks, but the files/folders are set to Smart Sync : Local.

There are other indexed filestructures that are added to other DevonThink Databases in Dropbox. These filestructures (which lie side by side) have not been deleted.

The files in DB that are deleted are indexed by DevonThink on machine B.
The files that are NOT deleted are indexed by DevonThink on machine A.
A Devonthink DB that is indexed on Machine A has been added as remote on Machine B. these files were NOT deleted.


A couple of ideas then:

  • check the (local, real) paths to a selection of files which are affected, and a selection of similar but unaffected files; I don’t use Dropbox, so can’t point you to the expected path (but for iCloud it is something like ~/Library/Mobile Documents/com~apple~CloudDocs/FolderName/ rather than iCloud Drive/FolderName/) - see if there are any differences which might point to the root cause of the problem.

  • Depending on what the path actually is, is it possible the contents are being affected by an automatic offload to iCloud (that would be the setting in the system preferences Apple ID/iCloud Drive Options…/Desktop & Document Folders)?

  • Give thought to what other differences there are between little Mac A and little Mac B.

  • When these deletions occur, are both Macs active (so either powered on, or in a sleep mode which allows them to sync Dropbox etc.)?

  • Are the Macs syncing DEVONthink via Dropbox exclusively, or are you using additional mechanisms (e.g. Bonjour, another cloud provider etc.)? It would certainly be worth following up on whether this problem occurs when the second Mac is completely powered down.

Have you spoken to Dropbox about this?

@BLUEFROG No, not yet. I saw there were som problems one year ago that was solved. Its still a mystery why only the folders indexed by Devonthink were affected and not others.

@Blanc , thanks for the tips!

The current hypothesis is that there is a special circumstance as follows:

  1. Computer B has an externally mounted SSD where the Dropbox files are located.
  2. Sometimes in Monterey there is a problem/bug that drops this mount, i.e. dropbox probably sees (some) files that are gone and therefore deletes them.
    2a. Not All files are deleted by Dropbox, i.e. files indexed by one devonthink database are deleted.
    2.b. I also noticed some files that were deleted were located as sisters to the folders indexed by DevonThink.

All in all, Im buying a new Mac computer sĂĄ I can store all files without an external SSD drive. Hopefully this will fix the problem.


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Thanks for the followup.

I don’t have luck with USB drives (spinning and SSD) with my macs. Eventually they all fail on me, mostly probably due to me disconnecting them accidentally or deliberately “too early” without eject. I keep backups of them, and I tend to have to reformat to fix. So I don’t “count” on them without backup,

What is the Dropbox location - the file path - on each Mac?

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The Dropbox is on externally mounted SSD.

Is the drive being ejected and connected to each Mac?