Problems with sync?

I have DEVONThink Pro 3 3.8.5 on my 13" MacBook Pro (2018 version). I also have DTTG on both my iPhone Pro Max 13 and my iPad Air. I have recently purchased the new iPhone and iPad Air, so this may be the source of my problems. I my previous iPhone XR and iPad 9th generation I was successfully syncing my DEVONThink Pro 3 main database and inboxes between my Mac and my iPhone and iPad. I haven’t checked DTTG on my iPhone and iPad since switching to the new devices. Now, when I look in DTTG on my iPhone, it shows the number 1808 next to my Global Inbox, but no files, no data, etc. On my iPad Air, there is a different (much lower) number next to my Global Inbox, as well as some files, but not nearly the number that show up in DEVONThink Pro 3 on my Mac.

What can I do to get sync working again properly for me? Should I delete DTTG on my iPhone and iPad Air and start over? Other suggestions? What am I missing here?


Did the sync actually finish or was it, maybe, interrupted?

  • What is reported in DEVONthink’s Window > Log?
  • Is there a triangle on the sync icon in DEVONthink To Go’s bottom toolbar? If so, tap it. What is reported?

Hi Jim,

  1. Is there a way to attach a copy of the log to a post here? If not, a message saying "The operation couldn’t be completed. (CKErrorDomain error 3.) with info “Not connected to Internet (CKErrorDomain 3)” appears at least three times over a period of the last week or so.

  2. In DTTG, the sync icon in the bottom toolbar is grayed out with no triangle. Clicking on the icon does nothing.


Using Apple’s Cloudkit or ICloud?


Starting yesterday I turned off the sync in DEVONThink Pro 3 until I get the problem with DTTG solved.

Using Apple’s sync servers surely the root cause. They are known to be unreliable as discussed here and with other apps for months. The “CKErrorDomain” error message is the tell.

Use another sync method. I use Dropbox and Bonjour with good reliability. Bonjour is the quickest.

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If I switch to Bonjour, what should I use for settings there: Port? Open Databases Automatically? And is the password something I set here? And then do I have to add that password somewhere in DTTG?

You don’t have to “switch” to Bonjour. You can add it as a second sync method. I will “just work”. You can keep Apple’s Cloud Kit if you want and hope/wait for it to work, but meantime, after setting up Bonjour and being in a situation where it works (both devices on local network), it will just work.

To set up Bonjour, rather than me repeating again here the instructions, please see the outstanding “DEVONthink Handbook”, page 60 of the current version (3.8.5). Supplemental information at Bonjour Simplified

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We prefer a support ticket for logs and machine info, etc.

  1. That’s a CloudKit error, not a sync issue.
  2. That indicates the sync location isn’t active or available. Have you checked DEVONthink To Go’s Settings > Sync: Locations to see if the sync location and databases are enabled to sync?

I’ve made sure iCloud (CloudKit) is enabled for syncing in DTTG’s settings on my iPhone, but I’m getting an “invalid encryption key” message now. I have the key saved in 1Password, but don’t see where to enter or change that key.

In DEVONthink To Go’s Settings > Sync: Locations, tap the Edit link, then tap the sync location to edit it’s options.

I’ve done that, Jim, but that’s where I get the “invalid encryption key” error message. I click on the CloudKit location, and have enabled the CloudKit location, then click through to the location to enable my Global Inbox and my Main Database, and they seem to attempt to sync, but in each case each ends up as “Not yet synced” and I get the error message “invalid encryption key.”

Look up the encryption key on the Mac…

  1. Do a Spotlight search for Keychain and open the Keychain Access application.
  2. In the logins section on the left, look for a key named DEVONcloudy Encryption (name of service) like DEVONcloudy Encryption (Dropbox).
  3. Double-click it and check the Show passwordcheckbox. You will be required to enter your Administrative password. (This is the password you use to log into your machine with.)
  4. Press Allow (or Always Allow, if desired) and the password will be shown.
  5. Take note of the password, then quit Keychain Access.