Help! Email account won't work in Mail, across 3 devices

Question

Level 1

77 points

Help! Email account won't work in Mail, across 3 devices

Hello,

I'd be so grateful if anyone can help me, this seems a really tricky problem.

Situation: I have a longstanding work email account which I need to access using the Mail app on three devices: a Mac Pro, a Macbook Air and an iPhone. All run different versions of the Mail app.

Problem: This email account is not working on any of these versions of the Mail app.

But, it works just fine when accessed via a browser and I've verified the settings many times.

History: the email account worked just fine for years on the Macbook Air but didn't run (also for years) on the Mac Pro. It ran ok for years on an old iPhone but I had to replace the phone and when I went to enter the details into the replacement iPhone, it wouldn't work. All three devices with all three versions of the Mail app are successfully running another email account (mac.com).

Details: the Mac Pro is running El Capitan and Mail 9.3; the Macbook Air is running Mojave and Mail 12.4; the iPhone is on iOS 13.7.

The accounts were linked via iCloud and I suspected a problem may have crept in on one device and become copied across all, so once I knew I could access this work account via a browser, I deleted the accounts from iCloud and re-entered the account details. This did not work and the account now doesn't work on any of the devices.

Mail variously reports that it can't log in to the server, or the password and/or username are incorrect (they aren't) or, more interestingly, that Mail is unable to send the password securely. In the latter case, after a long think it offers the option to continue by sending the password unsecurely. When I choose that option, I've had the incoming mail work (but very slowly) and then stop working. I've not managed to get it to find the outgoing mail server. Right now even the incoming isn't working.

I've verified the account settings with the provider. They are as follows (anonymised, obviously):

Secure SSL: yes

Username: name@othername.co.uk

Incoming server: mail.nameothername.co.uk IMAP port 993

Outgoing server: mail.nameothername.co.uk SMTP port 465

IMAP and SMTP require authentication

My IT support is able to set up this account no problem at all on her machine running Mail and also to access it via a browser, so it looks like the problem really isn't with the settings but is somewhere at my end on one or all three of my devices - weird, huh?

I've done everything I can think of with the advanced settings (relating to SSL, and the tickboxes about automatically detecting settings, etc) to no effect. I also tried removing the com.apple.mail.plist file (and others that looked similar) on one machine, to no effect.

The email account provider is not being helpful - they just tell me to upgrade the OS to Catalina, which is not an option on those machines, which are at their most recent possible updates. I'm certain it's not related to updates: it was running fine until yesterday on the MacBook Air and the problem exists on the brand new iPhone (iOS 13.7).

I'm out of ideas. Can anyone help?

Thank you!

Posted on Sep 9, 2020 11:22 AM

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Answer 1

TheLittles

Level 10

192,883 points

Sep 10, 2020 8:29 AM in response to Jason Woolfe

Jason Woolfe Said:

“Thanks. The App Password idea hasn't led directly to any changes in the situation yet[...]”

———-

You are welcome.

Getting this to All Interact:

If you Still cannot get it working as desired, then contact Apple and the eMail provider(s).

Contacting Apple Support:

Contact Us - Choose Locations
U.S.A. (800)MY-APPLE
Proceed from there as necessary

Contacting the eMail Provider:

Locate the eMail provider’s Contact Us information, usually in its own tab, or towards the bottom of the homepage. Look at their replies, and compare them to what Apple says over the phone:

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Answer 2

TheLittles

Level 10

192,883 points

Sep 9, 2020 11:41 AM in response to Jason Woolfe

Jason Woolfe Said:

"Help! Email account won't work in Mail, across 3 devices: Hello, I'd be so grateful if anyone can help me, this seems a really tricky problem. Situation: I have a longstanding work email account which I need to access using the Mail app on three devices: a Mac Pro, a Macbook Air and an iPhone. All run different versions of the Mail app. Problem: This email account is not working on any of these versions of the Mail app."

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Try Using a New Administrator User:

See what happens when you create a new Administrator User and login to it and perform the above. If it works, then it is something mid configured in your current user. So, move everything over to this new user, and then delete this user you are currently logged into.

Try Another Network - Restart your Router:

What happens when you try another network? Does that fit this. Also, Restart the Router - wait 30 seconds - power it back on. Also, disconnect from a VPN, particularly one that is maybe used for work.

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Answer 3

Jason Woolfe Author

Level 1

77 points

Sep 9, 2020 12:04 PM in response to TheLittles

Hi TheLittles, thank you for your reply.

I just tried your suggestion of creating a new Admin user. Here's what happened: the existing user account is also an Admin (on the Mac Pro) but is a standard user on the MacBook Air. Working on the Mac Pro, which is the machine I'm using right now to reply to this forum, I created a new Admin user account and entered the details into the 'clean' version of Mail.

The problem reoccurred exactly as before: it had a long think (=several minutes), then reported that it couldn't send the password securely, did I want to continue unsecurely? I chose not to, because I've tried that and it doesn't help.

Network: this is a new one, thanks for that. But I don't think it's the network. This is why. There's no VPN involved at all. Both computers (the Mac Pro and the MacBook Air) have connected via the same router, when the problem existed on the Mac Pro but not on the MacBook Air. The Mac Pro's connection is via cable and the laptop connects via wifi, but I don't think that's significant. When using the laptop elsewhere (ie connecting via another wifi network, other routers), I never had a problem on the MacBook Air. The iPhone connects via Wifi or mobile network and the problem exists there, too.

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Answer 4

Jason Woolfe Author

Level 1

77 points

Sep 9, 2020 12:21 PM in response to TheLittles

Hey - TheLittle, if you're still there,

I have something to report!

Following writing my reply to you just now, I thought I'd try following your suggestion on the MacBook Air instead of the MacPro. So... I created a new admin user account, and entered the details (exactly the same - I know them off by heart now) into that copy of Mail.

It went through immediately (no waiting), signed in and... hey presto! A full inbox!

So, the incoming mail server works. And I just tested by sending an email and the outgoing works as well. Success!

So, this is great. It's working on one device. Now, how do I copy that across to the other two devices?

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Answer 5

Jason Woolfe Author

Level 1

77 points

Sep 9, 2020 12:30 PM in response to Jason Woolfe

And just another follow-up: I've entered the same details into the iPhone and get the familiar error message: Cannot Send Mail. The username or password for 'account name' is incorrect.

So, it's now working on the laptop but not the other two. Account details are the same all round. How can it be connected with a user account if it occurs on a phone?

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Answer 6

TheLittles

Level 10

192,883 points

Sep 9, 2020 12:57 PM in response to Jason Woolfe

Jason Woolfe Said:

"Help! Email account won't work in Mail, across 3 devices: And just another follow-up: I've entered the same details into the iPhone and get the familiar error message: Cannot Send Mail. The username or password for 'account name' is incorrect. So, it's now working on the laptop but not the other two. Account details are the same all round. How can it be connected with a user account if it occurs on a phone?"

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Use a New App Password:

Being that you are using the Mail app, you may need to use an App Password. So, I recommend trying a new App Password. If that does not work, I recommend removing the accounts, then adding them back. Be sure you use a separate App Password for each device.

For example, on Yahoo: Generate and manage third-party app passwords - Yahoo Support

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Answer 7

Jason Woolfe Author

Level 1

77 points

Sep 9, 2020 1:15 PM in response to TheLittles

Thank you for your time, it's appreciated.

I'm not sure I understand what's meant by an App Password. If it's the password used to access the email account, then my IT support person already tried changing that (in case there was a problem with one of the characters) with no effect.

If it's not the email account password, then what is it? I don't use Yahoo but have read that page you linked to, from which my understanding is that perhaps the email account can somehow have an password for a device, separate from the mail server access. So I went poking about in the settings that I can access via the browser (webmail). I see nothing particularly like a password, but I did find a script to auto-set up the email settings. I tried that just to see what happens and at the moment it's reporting that it can't run because 'the account already exists' on this machine. I'm unwilling to delete it right now, because doing so would remove it from iCloud which would remove it from my laptop, where it's currently working. Or do you think I should try that? Sorry if I've misunderstood, I think I've drifted off your original point. I don't know about/can't see an App Password.

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Answer 8

TheLittles

Level 10

192,883 points

Sep 9, 2020 1:39 PM in response to Jason Woolfe

Jason Woolfe Said:

"Help! Email account won't work in Mail, across 3 devices: Thank you for your time, it's appreciated. I'm not sure I understand what's meant by an App Password. If it's the password used to access the email account, then my IT support person already tried changing that (in case there was a problem with one of the characters) with no effect. If it's not the email account password, then what is it?[...]"

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About App Passwords:

Without letting me know: Is this eMail account from work or school? Or is it from a public domain (i.e. Yahoo, AOL, Outlook(Hotmail), GMAIL, etc.)? If from a public domain, then you need to add it using an App Password in order to synchronize it. It is all about Security & Privacy. Contact your eMail Provider for more on setting this up.

Use your Official eMail:

So, using the Mail App, you add the account to the device, simply by entering your official eMail address, and then use the App Password that was just created, for the password. It may take unto 48 hours for it all to sync, once logged in.

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Answer 9

TheLittles

Level 10

192,883 points

Sep 9, 2020 1:42 PM in response to Jason Woolfe

Jason Woolfe Said:

"Help! Email account won't work in Mail, across 3 devices: [...]I'm unwilling to delete it right now, because doing so would remove it from iCloud which would remove it from my laptop, where it's currently working. Or do you think I should try that? Sorry if I've misunderstood, I think I've drifted off your original point. I don't know about/can't see an App Password."

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Remove it Later:

Remove it from iCloud, then add it back, when you are currently not in the need for using your eMail Account (maybe in the middle of the night, assuming that's when you'd be sleeping and not using your phone). It may take unto 48 hours for it all to sync, once logged in. Your Apple ID would still be what it is. IOW: There is no requirement for an eMail account to be added to Mail.

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Answer 10

Jason Woolfe Author

Level 1

77 points

Sep 9, 2020 11:45 PM in response to TheLittles

Thanks. The App Password idea hasn't led directly to any changes in the situation yet and I've not yet (haven't had a suitable opportunity) removed the account from iCloud but I can report that I've now got the account running smoothly in my normal (non-Admin) user account on the MacBook Air. It isn't slow, it runs perfectly fine, just as I'd normally expect.

I struggle to make much sense of this and it's still reporting the familiar error messages on the other two devices.

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