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Macmail switching to MD5 challenge-response

Hi. My mac mail keeps switching its authentication from password to MD5 challenge-response. It seems only to be messing up one of my two email addresses, and it keeps changing from not sending to not receiving, all very arbitrary. I change it back to password, and have tried quitting mail, restarting the computer, and the authentication keeps switching back to MD5 challenge-response. Any ideas? Thanks.

IMAC (RETINA 5K, 27-INCH, LATE 2015)

Posted on Mar 15, 2018 4:11 PM

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Posted on Mar 15, 2018 8:54 PM

Turn off the “automatically scribble on my mail server settings seemingly randomly” option in the mail preferences. Okay, I’m paraphrasing that slightly, but there’s really a checkbox in the server settings that does basically that. Automatically manage connection settings in Mail on your Mac - Apple Support Try disabling that, and see if the settings stick.

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Macmail switching to MD5 challenge-response

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