Sync hangs on MacBook Pro while works on iOS reliably

I have an update to a prior issue I thought was resolved, but unfortunately it still alludes me after several months of trying different things.

Current version of MacPro app : 3.0.4
Sync Location is Dropbox

I don’t believe it’s necessarily a bug, but I cannot determine how to get this to work for me.

When I go to Preferences | Sync | Locations and select the DEVONthinkPro1 item, I see the spinning disk next to one of the databases (the specific database changes). The dates show that the last Syncronization occurred some time ago and it won’t ever change or update.

When I look at iOS the files I added to the iPhone and iPad are syncing fine between themselves but don’t show the files I added recently (after the last successful sync) on the MacBook Pro. Files I added to the iOS app on either device do not appear on the MacBook Pro. This had me puzzled before I saw the sync was hanging.

How I “fix” or “force” the sync. I shutdown the MacBook Pro App. This requires TWO ‘Quits’ to shutdown (this indicates to me that it’s hung somewhere and won’t allow it to close on the first quit). NOT at “force quit” just a second ‘Quit’ will close the MacBook Pro App. When I restart the app and I navigate back to Preferences | Sync | Locations I can see that the system is ‘downloading’ files and syncing fine. After this, and only after this do I see the files added to the iOS and the MacBook on the other device apps.

(Hopefully this makes sense)

My feeling is something is causing this to hang and I have no idea how to determine what it is. That it does not hang on any particular Database either indicates that each database has something wrong or it’s something else.

Does this report anything: ?

It is blank, only shows the Dropbox Icon, nothing below the line

I think it may be the VPN I have running. I switched to use a ‘Split Tunnel’ to allow DEVONthink and Dropbox to not use the VPN. For now it appears to be working. No hangs.

Interesting. What VPN are you using?

Private Internet Access (

Came here searching for a solution to this problem too! Wanted to say that I’ve been having exactly the same problems recently after switching from iCloud sync to Dropbox.

Syncing will seem to just get “stuck” after a while. After restarting DT (with the same two quits required), it’ll start syncing again, but eventually stop working again.

The VPN thing is interesting as I’m having problems on my work system that is normally connected via VPN to my work network. I’ll need to play around with my other system and see if it’s just the one computer I’m having problems with.

Would love to see some sort of resolution to this! Especially since iCloud sync wasn’t working as well I’d have liked.

I can confirm that after a few (3?) days now it continues to sync without anyintervention. This is longer than ever before and a wonderful thing. Previously the problem would resurface within a few hours, I’ve never gone a full day.
Essentially by “split tunneling” set within my VPN app I was able to set both DT and Dropbox to not use VPN.
If someone wants me to try resetting one or the other back to using VPN in order to see what happens I am happy to accommodate. Though I have to admit to some level of superstition at this point as I fear to mess around with something I really don’t understand which also appears to be working - lol.

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If you’d like to test the theory we would welcome the info, but if you’d rather “if it’s not broke, don’t fix it” :slight_smile: , we’re okay with that too.