On 22 Jan 2018, at 7:01, Bill Cole wrote:

On 18 Jan 2018, at 22:01 (-0500), Randall Gellens wrote:

Mailmate keeps asking for my mail.mac.com password. I created an app-specific one for it, entered it when creating the account earlier today, and checked "save in keychain." Looking in the keychain, I see it. However, MM has asked for it several times, saying it isn't in the keychain. The existing keychain entry has modified time updated when I re-enter it.

Does it actually work when you enter it manually?

It seems to.  I don’t see an error in MM.


Apple's mail system has a history of authentication flakiness, with periods where some nodes have required a bare username while others only work with the full email address as username. Also, they have been moving away from the mac.com domain for a while, and while I think mail.mac.com should still work, it's fast-flux DNS via Akamai is much faster (30s) than the {imap,smtp}.mail.me.com hostnames given at https://support.apple.com/en-us/HT202304 and that can cause glitches.

What are the optimal servers to use?


If authentication is reliably working when the password is entered manually, this could be a problem with your keychain settings or the specific keychain item. If you have your keychain set to lock after a period of inactivity or when sleeping, an app like MM can misinterpret the inability to access a keychain item as the item being gone or wrong and not bother to recheck the item the next time it's needed. When the machine wakes up and the keychain unlocked, the app tries to fix the "bad" item with a new password.

That could be it.
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