Weird Email Problem in Apple Mail

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Level 2

368 points

Weird Email Problem in Apple Mail

2016 iMac, 10.14.6

I have 3 devices with the same Microsoft Exchange email settings > iPhone, MacBook, & iMac. 3 days ago on the iMac, the alert "Can't connect to the account" appeared. No incoming or outgoing emails possible. When I clicked on it, it asked for the password. Then, after I entered the 100% correct password, it returned: "Unable to verify account name or password."

I opened the account prefs and retyped the name and password: "Unable to verify..." Tried this multiple times.

The server is shown to be offline.

I backed up and then tried to open another account with a different name, but couldn't: "Unable to verify..."

Here's the weird part: I looked at my phone. The account functioned perfectly. I tried the Macbook: no problem there either.

They both have the exact same settings. So it's a Mac problem, not a Microsoft Exchange problem.

I assume there's some sort of corruption in the iMac Apple Mail account but that doesn't explain why the correct settings in a new account can't be verified.

Also, I can access the Microsoft Exchange webmail on the iMac using the same password.

As well, another weird thing, when I send an email FROM the webmail account to the Apple Mail account on the iMac, it shows up in the Apple Mail inbox but none of the other mail in the webmail inbox downloads.

Any help with this problem would be greatly appreciated.

iMac, OS X 10.11

Posted on Jun 12, 2023 3:38 AM

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Answer 1

Top-ranking reply

KiltedTim

Level 10

228,402 points

Jun 18, 2023 10:04 AM in response to bookmanjb

The version of macOS you are running is not compatible with the authentication that is now required by Exchange.

Legacy authentication is no longer supported by Microsoft.

You'll be limited to web mail unless you can upgrade macOS to a version that's supported by Exchange/MS 365.

That means at least macOS 11 Big Sur.

What model Mac do you actually have? There is no such thing as a 2016 iMac.

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Answer 2

Jun 14, 2023 7:19 AM in response to bookmanjb

Hello bookmanjb,

We understand you need help with Mail on your iMac. It's helpful that you seem to have already narrowed down the issue a bit confirming your account settings and that it works on other Apple devices. Since it's specific to your iMac for the time being, we have additional steps to continue ruling out possible causes.

Boot your iMac to safe mode. See if the error occurs with your mail account.

Start up your Mac in safe mode - Apple Support

Then, we'd recommend creating a test user, logging in to it and configuring that account. See if you get the same error. This will identify if the issue is specific to your user profile.

Set up users, guests, and groups on Mac - Apple Support

Reply back with how it goes.

Best regards.

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Answer 3

KiltedTim

Level 10

228,402 points

Jun 18, 2023 3:08 PM in response to bookmanjb

It will stop working on the MacBook as soon as the current authentication token on that device expires.

Exchange Online/MS 365 now requires modern authentication for all clients.

https://www.microsoft.com/en-us/microsoft-365/blog/2022/09/01/microsoft-retires-basic-authentication-in-exchange-online/

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Answer 4

KiltedTim

Level 10

228,402 points

Jun 18, 2023 10:49 AM in response to bookmanjb

Your MacBook and your phone are NOT running the same OS...

You need to upgrade macOS on your iMac to Big Sur.

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Answer 5

Chris_C1

Community Specialist

Jun 18, 2023 9:53 AM in response to bookmanjb

Hey there bookmanjb,

Since you are receiving the same error in safe mode and a new user, you'll want to reach out to your email provider to verify required settings or troubleshoot login credentials.

Have a good one!

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Answer 6

bookmanjb Author

Level 2

368 points

Jun 18, 2023 2:40 AM in response to Soosie_J215

Hi Soosie, Well, I tried rebooting in Safe Mode. Same problem. Then I created a new user, TestMail, and tried to create a new Mail account. No go. I went through the following steps:

And nothing further appeared. When I hit cancel, it took me back to Mail Prefs.

When I tried again using Configure Manually, I entered my password:

I hope this info gives you some clue as to what is going on. I'm baffled. Thanks.

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Answer 7

bookmanjb Author

Level 2

368 points

Jun 18, 2023 10:39 AM in response to KiltedTim

Late 2015. Model Identifier: iMac16,2

Processor Name: Intel Core i5

Email was working fine until a week ago. Was there some kind of cutoff date? Btw, I have the exact same OS version on my 2017 Retina MacBook and the email works fine.

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Answer 8

bookmanjb Author

Level 2

368 points

Jun 18, 2023 11:07 AM in response to KiltedTim

You've misunderstood the situation. My MacBook and my iMac are both running OS 10.14.6, Mojave. The login to Exchange works fine on the MacBook. Up until a week ago, it worked fine on the iMac. I mentioned the iPhone because the login to Exchange is the same and it also works fine.

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