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<p dir="auto">I had a problem very much like this a few weeks ago. When I came back to my machine after leaving MM running overnight it would prompt me for some or all of the passwords for the 5 IMAP accounts that I normally use. I discovered that if I just dismissed those dialogs MM would try again and get the PW from the Keychain with no problem. With some help I got MM to log what it was doing and discovered that it was trying to access the keychain while the machine thought it was in "dark wake" mode. This is Apple's internal name for Power Nap. There are two problems with this: I don't have Power Nap enabled and MM wasn't doing anything that should require the GUI to be active. I gave up trying to find the problem and it eventually went away as mysteriously as it started.</p>
<p dir="auto">I don't use SSH or NAT. Some of the servers are on my local network and some aren't.</p>
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<p dir="auto">On 15 Jul 2020, at 12:22, Randall Gellens wrote:</p>
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<p dir="auto">I agree it seems (from what I can see) that MM thinks network problems are authentication problems. What's interesting is that the dialog box is for iCloud, which is not affected by the SSH issue. I also just now discovered that the dialog box can go away on its own. This morning, the laptop SSH connection had dropped, as has been happening the past few days. MM had the dialog box up asking for the iCloud password, and was displaying "(not available)" for those accounts that are reached over SSH (not iCloud). Without touching MM, I hunted in Keychain Access for the imap.mail.me.com password, and at one point when I went back to MM to check the exact wording in the dialog box, it had vanished. I hadn't yet reestablished the SSH, so the those accounts were still greyed out with "(not available)".</p>
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