Mail can't verify the identity of the server outlook.office365.com (Passwordless account)

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Level 1

9 points

Mail can't verify the identity of the server outlook.office365.com (Passwordless account)

I have a Microsoft Exchange email account set up in mail (Catalina 10.15.7) on Mac. I've switched to passwordless access & use Microsoft's password app generator to produce a password for verification. Everything works fine for about a week then I get the above warning & cannot download any emails. If I delete the account, reinstall & generate a new password mail will work fine again for another week.

I've tried to trust the certificate but there is no "Show certificate" button in the warning box. I've been through key chain but can't find the certificate. Outlook works fine on my iPhone.

If anyone can point me in the right direction as I've search everywhere for an answer and can't find anything. Deleting the account & reinstalling weekly is a pain.

iMac 27″, macOS 10.15

Posted on Aug 12, 2022 03:16 AM

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Answer 1

ASTRO24

Community Specialist

Aug 13, 2022 02:48 PM in response to Walenut

Hi Walenut,

Thanks for posting in Apple Communities.

For this issue with your mail error, try connecting to a different Wi-Fi network and make sure that you have the recommended network settings in place. If you have any security software installed, disable it. If your computer is connected to a VPN, temporarily disable it and check for the same behavior.

Regards.

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Answer 2

Walenut Author

Level 1

9 points

Aug 13, 2022 11:39 PM in response to ASTRO24

Hi Astro,

Many thanks for the reply. No VPN & no security software other than what's included with Catalina. I'm connected to the router via a data cable however wifi is also enabled. I don't have any other Wi-Fi network but the router is dual band. I'll check the network settings. The rest of the family use this router via wifi with Mac books & iPhones & I use it with my iPhone with no issues.

Regards,

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Answer 3

chuckbl

Community Specialist

Aug 14, 2022 09:47 AM in response to Walenut

Walenut,

When this behavior occurs, are you still able to access your email using the Outlook website on your Mac?

Also, do you have any other email accounts set up on your Mac? If so, are you experiencing any difficulties with your other email accounts?

Hopefully those details will help to isolate this further so we can provide the best guidance possible.

Take care.

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Answer 4

Walenut Author

Level 1

9 points

Aug 15, 2022 01:56 AM in response to chuckbl

Hi chuckbl,

Thanks for the reply. Yes I can access outlook via the website. I have 2 other mail accounts set up and both continue to work correctly.

Regards,

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Mail can't verify the identity of the server outlook.office365.com (Passwordless account)

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