Resolving repeated requests for authentication

OmniFocus needs a password to access your Omni Sync Server account, and an encryption passphrase to decrypt the synced copy of your OmniFocus database stored there. For most OmniFocus users, the password and passphrase are the same (linked).

An authentication request is something OmniFocus is intended to handle automatically, only asking for more information when something unexpected happens. Recently, though, some OmniFocus users have gotten repeated prompts for authentication. If you see "The server ‘Omni Sync’ requires authentication’ prompt pop up more than two times, try the following troubleshooting steps.

Check for correct password

You may be entering an incorrect password. For help recovering your password, please reference: Resolving Omni Sync Server password issues. For help with encryption passphrase issues, please reference: Recovering your OmniFocus encryption passphrase.

Try a Safe Mode Reboot

It sounds like a technical support cliché, but we have seen this help in a lot of situations, especially if you have recently updated your operating system. Instructions for booting into Safe Mode can be found on Apple’s Support site, here. Make sure you reboot into normal mode again after doing this!

Delete OmniFocus, Restart, & Re-install

  1. Delete OmniFocus by opening a Finder window and dragging the icon from your Applications folder to the trash. This will not delete your database.
  2. Restart your Mac.
  3. Download and re-install OmniFocus (from our website or from the Mac App Store).

Delete Old Keychain Entries

  1. Make sure you know your current OmniFocus password/passphrase.
  2. On a Mac, open Applications/Utilities/Keychain
  3. In the search field, type omni.
  4. Find entries in the list named or sync[#]
  5. Delete all the matching Keychain entries.

The next time you open OmniFocus, you will be prompted for your password. Make sure to check the “Remember in Keychain” box to allow Keychain to create a fresh entry for Enter your password, and click OK.

If you’re still seeing repeated prompts…

…please contact our Support team at! We’re always happy to help.

I had the same issues and could solve it now, it was the iCloud Keychain which caused the problem. I guess the problem is on Apples side not on the side of OF?

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