Files not syncing on iCloud sync on second computer (shows cloud and index icon beside files)


I’ve added Devonthink to my second old Mac running High Sierra so I can use DTP3 at home. I’m using iCloud sync. My main MacBook Air for work is on Catalina.

Problem is on my old High Sierra Mac, my database is not syncing properly. Half of the groups and files have the indexing icon and the cloud icon and are greyed out.

I’ve signed out and into iCloud, I’ve rebooted both machines, can’t figure it out.

I once had an indexed drive set up on the new machine but I moved that back into DTP3. I don’t know if that’s the problem. Or maybe a problem with HighSierra/Catalina compatibility?

Very frustrating

Thanks for your suggestions.

On the problematic machine, hold the Option key and choose Help > Report Bug to start a support ticket.

I am currently having basically the same problem, although I use Bonjour sync. In my case, one of my Macs is running Monterrey (Server) and the other Sonoma (Client).

The problem is on the Sonoma Mac where a group (and all of its sub-groups) is greyed out and have both the cloud and indexing icons. The actual files (documents?) are present in the groups, however, without any icons. Below is a screenshot from the client Mac:

And did you do a File > Verify & Repair Database on the server Mac?

I just did…verified successfully.

Oh…wait. You said the server Mac. Yes, I did this before the sync, and I do it regularly on the server Mac, as it is the one I mainly use.

  • Is that group actually indexed?
    • If so, why that one when the other similar ones aren’t?

The problem group was originally indexed before I switched to importing. The other groups shown above this group were created after I had switched my method to importing.

  • Is it still indexed on the server Mac?
    • If so, why not use Data > Move Into Database, then sync the client Mac?

ok…I clicked on the group (405_3_2), executed the Data> Move Into Database, then performed a sync. Now the client Mac looks just like the server mac i.e. with the greyed folder icons and cloud symbols!

If I click on the folder again, and go to Data, then “move into database” is greyed out.

Pretty frustrating.

Where was that indexed folder in the Finder?

It is in a OneDrive folder:
Macintosh HD–>Users–>username–>OneDrive–>Documents–>Myrdal–>Archives–>ARAB–>405_3_2

  • Are you sure you are logged in to OneDrive (I notice sometimes I have to re-login, dunno why)
  • Are the files set to “Always Keep on this Device”, i.e. local on the drive (as DEVONthink may not find files located on Microsoft’s servers)

I don’t use Microsoft Onedrive for files indexed into DEVONthink. I also don’t have many files indexed and rely on imported files as simpler and more reliable. I only index if those files are required by other people or applications. See the “DEVONthink Manual” for discussion of the potential issues you need to be aware of for index files, esp. when located in folders that are synced with Could services.

Hi and thanks for your response!

The answer to both of your questions is yes. Also, I became aware of all of the pitfalls with using Indexed files a while ago, which is why I switched to importing.

All of the actual files within the groups are imported (and do not show the ‘Indexed’ icon. For some reason, though, the Indexed icon still exists on the group level along with the Cloud icon.

Does File > Update Indexed Items fix this assuming that the path of the indexed items is correct and the files/folders are locally available?

No…that does not fix it and, yes, the path of the “indexed items” is correct and all are marked as locally available.

While I am not sure what the problem is, for me it is mostly a cosmetic issue. The actual files in the groups are imported into DT (as displayed in the screenshot in my original post), and everything works fine. But I don’t want to experience a problem in the future.

What about moving the imported files into a new group and simply trashing the old one? This should definitely work.