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I know there have been bugs that cause macOS (or the Mail app) to ask for the Exchange password repeatedly, but this is different from those. The issue I'm having is that I receive a notification for the Exchange password and can click the notification's Continue button to make it display the Internet Accounts window but it never actually prompts me to enter a password. When I view the entry for the Exchange account in Keychain Access, what it has is correct. I have deleted the account entirely and re-added it to no avail, and I've also replaced the Keychain entry with an app-specific password to make sure that MFA wasn't interfering somehow. I still receive the notifications. Nothing is actually broken that I can find (I still receive mail and calendar events without any issues), so I'm fairly certain this is just an annoyance/cosmetic bug. Has anyone got any ideas what could be the cause for this and how to resolve it?

I'm on a MacBook Pro (14-inch, 2021) with an Apple M1 Pro running macOS 12.1 (21C52).

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    I have a similar issue with an Office365 account. If at any point, the server doesn't respond properly, then it asks for the password again. I avoid this like the plague, because once a password is entered it is rejected by Outlook & you have to reset it online. This is entirely an Office bug. I've spoken to tech support about it & "there's nothing they can do." The trick is to wait it out. If it doesn't reset by just setting all accounts online again, then quit & relaunch Mail will usually shake it out.
    – Tetsujin
    Commented Jan 3, 2022 at 15:57
  • @Tetsujin Same. It does correlate to connection issues on the far/remote side but it seems strange that it displays a password prompt (or rather a notification about a password failure but NOT an actual password prompt) rather than a connection timeout or other error to signify a connectivity problem, not an authentication problem.
    – Jesse P.
    Commented Jan 3, 2022 at 16:01
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    @Tetsujin That’s not the same as my issue, then. Like I said in the original post, I get a notification and clicking continue displays the Internet Accounts window but that’s it - no box to actually enter a password. And nothing stops working, so it’s like it’s showing the notification for no reason at all. The only similarity to your issue is that I’ve noticed is that it happens more frequently after the MBP has been asleep and may not be actively connected to the network.
    – Jesse P.
    Commented Jan 3, 2022 at 16:29
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    Hmm… similar but different then… BTW, this has been ongoing from El Capitan right to Big Sur, across all the Macs in the house - all using the same 365 structure as a business account through BT in the UK.
    – Tetsujin
    Commented Jan 3, 2022 at 16:30
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    @Tetsujin I know. It happens on my mid-2012 MBP as well sometimes, which can’t be updated past Catalina, but I don’t really care about that MBP since I don’t use it much anymore anyway. It seems much more prevalent on Monterey, which doesn’t really surprise me given the amount of bugs in that OS in general.
    – Jesse P.
    Commented Jan 3, 2022 at 16:32

2 Answers 2

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The solution described here seems to help Basically, it suggests going to the Key Chain and deleting certificates for office, exchange, and Adal.

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    That may help some, but that’s not the issue in my case. It seems to just be some sort of background check that’s being attempted, and because WiFi disconnects after a while when the lid is closed, it loses the ability to actually complete this check. Rather than being designed to simply timeout or say there was no connection, it was designed to say that the credentials are bad even when they aren’t.
    – Jesse P.
    Commented Sep 19, 2022 at 12:05
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A possible solution, once the internet account opens, try clicking on the exchange account and then "details" (this usually prompts for the password again)

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    It doesn’t, and like I said already, the password it already has is correct and nothing actually stops working even though it asks.
    – Jesse P.
    Commented Jan 3, 2022 at 18:06

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