Deletion Syncing/Indexing No Longer Working Properly

MacOS 26.5.1

Indexed Database, with folder system using Dropbox to sync w/ other computers. Nothing is imported - only indexed.

Not sure when this started, but deletion sync no longer seems to work (where it has worked for several years prior). Essentially, I can delete files from DEVONthink - but they do not get deleted from Dropbox. All the files are still there, and when/if the folder re-indexes, the files come back.

I can’t figure out what is causing this. I’ve attempted to rebuild the index, make sure the Full Disk Access is enabled, made sure Dropbox is running, etc. Nothing seems to be working.

Any ideas of what’s happening? This issue is actively preventing me from being able to use DEVONthink effectively.

Firstly, have you read and understood the In & Out > Importing & Indexing section of the built-in Help and manual?

Secondly, have you emptied the database’s Trash?

Yes and yes. Emptying the trash doesn’t do anything - it just “removes” it from the indexed db, but the files remain on disk. They are all indexed, and reappear when the folder is rescanned. I’ve even tried rebuilding the full database to see if that would help.

This used to work until some point over the last month or so. Not sure what’s happening.

Did you index the same items e.g. to multiple groups or databases?

No - it’s basically “Company Folder” > “My Folder”, and my folder is specifically the one indexed. I essentially use DT as a glorified file manager with some enhanced capabilities and keep it intentionally simple.

The handling of indexed files & folders is the same in DEVONthink 4.3.x. Did this e.g. start after udpating to macOS 26.5.1? Does this only affect Dropbox or also local folders?

I quickly created a new test db for non-dropbox. It appears to work fine there, so it seems to be something to do with Dropbox.

This may have begun after updating to MacOS 26.5.1, but I can’t be certain.

It almost acts like there’s no delete access for Dropbox, although there is Read/Write.

Do you experience the same using iCloud Drive? I wonder whether it’s a generic cloud issue or limited to Dropbox (and maybe a recent update).

If it is useful, @cgrunenberg what happens with “do not ask me anymore” (or similar text) when you select DON’T delete the indexed files? Do they never got deleted until you re-enable the check option and select delete the files?

Your answer (delete or do not delete) is remembered in this case.

Then, if he selects do not delete and do not disturb, now each time he deletes an indexed file, it is only removed from the database, and that could be the culprit.

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Indeed. Then resetting alerts in Settings > General > General should fix this.

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Well, good news - it does appear to have been the do not ask me anymore prompt… which is strange, because I’ve had it disabled for months. It makes me think something changed my answer, but I have no proof of it.

Regardless, the resetting the alerts brought back the prompt and I was able to delete the files. Appreciate the help!

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