I have a MacBook Pro [insert the specs]. Ever since Catalina I have had a problem with continually having to enter my iCloud information. This occurred on my old MacBook pro immediately following upgrading to Catalina, and now having upgraded my computer and starting out fresh on this MacBook Pro [I did not restore from backup, it is straight out of the box and setup as new], the problem is back yet again. First, I do have file vault turned on. I have to users on this computer one is my personal user ID and one is my work one used for when I’m teaching college courses. The personal one has everything for iCloud turned on except saving desktop and documents to iCloud. The work one is setup with iCloud but only iCloud data (pages, keynote, numbers, iCal, and being able to see the actual iCloud drive to see files if needed).
Well, periodically (several times a week) when I log onto either side, I notice a badge on system preferences and when I check it, I get the attached message indicating I need to sign into iCloud again. After doing so, I check, and every time Keychain is unchecked. I’ll go about my business and need to switch sides, and the same thing has happened on that side. I go through the steps, it logs in, I have to select keychain again on that user and all is good for a day or so.
Then, for whatever reason a couple of days passes, and the process starts over again… every time Keychain is unchecked…
Is this a Catalina issue, a file vault issue, having multiple users on one MacBook Pro issue, a combination of all of the above… how can I fix this?
Well, periodically (several times a week) when I log onto either side, I notice a badge on system preferences and when I check it, I get the attached message indicating I need to sign into iCloud again. After doing so, I check, and every time Keychain is unchecked. I’ll go about my business and need to switch sides, and the same thing has happened on that side. I go through the steps, it logs in, I have to select keychain again on that user and all is good for a day or so.
Then, for whatever reason a couple of days passes, and the process starts over again… every time Keychain is unchecked…
Is this a Catalina issue, a file vault issue, having multiple users on one MacBook Pro issue, a combination of all of the above… how can I fix this?