I had the same problem, when the dialog box pops up to sign in, type the password, but before you hit enter, look at the dialog box, it has a few choices. As I don’t get the dialog box any more, I can no longer tell you the exact words, but one of them is to always use this password, or not to ask again or something. Make sure to click on that instead of just hitting enter
I am having this issue wtih Omnifocus v3.12.2 (v149.17.43). It asks twice, usually when I wake up the Macbook in the morning. The dialog is sitting there waiting for me. I enter the password, and then I am prompted again with the same dialog. I enter the password again, and I am good for the day. This has been happening daily for quite some time now.
Here the same. It happens since Monterey and specially after waking up the MacBook. I keep ignoring the dialog as just restarting the OF helps. Nevertheless it’s annoying and need to be confirmed and fixed.
No, you’re not the only people having the same problem. I guess it can be a kind of security measure, but it’s really annoying. And as I see, no one found the solution. It’s a pity though.
I just noticed a second dialog when exiting OF in this situation.
It tells that it is updating the security token. After this it is working again.
Wish OF would follow the problems that are being discussed here and give a statement.
I could solve it with the ‘always allow’ option in the dialog that asks you fpr the password (twice). But I also un-installed OF2 and just left OF3 12.2 in my Mac / Monterey, so I’m not sure which did the trick.
I also get this dialog twice but it’s just a password field without the ability to check additional options to remember the password. I don’t have OF2 installed.