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Cannot send e-mail

I upgraded to OS X Yosemite a couple of days ago and today my e-mail stopped working. I have a POP account and use a Plusnet account. I've managed to restore the incoming e-mail but continue to not be able to send e-mail.

I've searched through the Apple support forum and other internet forum and have tried some of the suggestions for dealing with Mail issues such as disabling the automatic detect and maintain account settings options and have allowed insecure authentication. I have also spoken to my e-mail/internet provider and they could not resolve the issue on their end.

I'm using port 587 (which the e-mail provider confirms is correct), have unchecked SSL and the e-mail and account details all seem fine.

Could anyone suggest anything that might get sending e-mails using Mail working again? Should I revert to Mavericks (if this is possible) where I had no problems with Mail?

Many thanks

MacBook Pro (13-inch Mid 2009), OS X Yosemite (10.10)

Posted on Nov 2, 2014 1:09 PM

39 replies

David1248 Author

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Nov 6, 2014 1:02 PM in response to blackxacto

Hi - I have tried deleting and re-adding the STMP server details and passwords without success. Would have been great if this had worked for me. Perhaps I am simply doing something wrong?

Thanks

David

Nov 6, 2014 1:06 PM in response to David1248

Yosemite Apple Mail/Window/Connection Doctor.

Run and what connections are showing red?

David1248 Author

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Nov 6, 2014 1:11 PM in response to blackxacto

The POP account is green (I can receive e-mails) but the SMTP account remains red (so I can't send any e-mails). I've deleted the account and re-entered manually (and have had my internet provider do the same), I've unchecked SSL, I've unchecked the automatic detect and maintain settings in all the relevant places, I've switched port numbers between 25 and 587. Not sure what else I can do as I seem to have exhausted all the suggestions others have kindly made.

Thanks

David

Nov 6, 2014 1:16 PM in response to David1248

Mr. David, please bear w me, when you say you have deleted accounts, did you delete both IMAP servers AND SMTP servers. They must be deleted separately in two separate actions. I could not delete my email accounts and expect the SMTP servers to be deleted as well. They must be deleted manually, separate from the email account deletion.

David1248 Author

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Nov 6, 2014 1:21 PM in response to blackxacto

That's correct. I've completely deleted the account and re-entered in full. I've also separately deleted the POP account and the SMTP account (via the edit SMTP server window). Is this what you mean by deleting separately or is there a different location on the Mac that I should be looking at?

Thanks

David

Nov 6, 2014 1:29 PM in response to David1248

Whoa, yes, the SMTP server window must be used. Sorry, this didn't help. It worked for me. I have not been able to send email from Apple Mail for two weeks after upgrading to Yosemite. Glad to have it back after deleting my SMTP servers and re-entering them.

The only thing I can think of is a bad password or a wrong typed address, but I'm sure your tired of hearing all this. Might be worth calling Apple and buying $17 service tech. Call it continuing street school. I'm still studying at that university. 🙂

Nov 15, 2014 8:24 AM in response to Linc Davis

Hello Linc

I have the identical problem and have also followed through the steps you advise above.

I use: mail.authsmtp.com

Any help appreciated.

Thanks

Paul

David1248 Author

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Nov 15, 2014 11:21 AM in response to paulfrom34

Hi Paul

I eventually found a solution to the issue - not from the Apple Support Community but from my internet provider - as per below. It works for me and if it works for you, I suspect that this may impact the security of your e-mail so I would take care as to whether this is the right solution for you.

Hope it helps

David

"Quit mail

Open up Finder

In the Finder menu bar select Go > Go to folder

type in ~/Library and click Go (on my keyboard the "~" is next to the left shift key)

Open the folder Mail

Open the folder V2

Open the folder MailData

Double click to open Accounts.plist (should open in TextEdit)

Find the block of data that contains the offending mail account

Find the line within this block that says UserAllowsInsecureAuthentication

Change the line below this from to false to true

Quit TextEdit

Restart mail"

Nov 16, 2014 9:49 AM in response to David1248

Thankyou David for your timely clear and accurate help.

Yes found in fact two blocks of data referring to the SMTP server and did precisely what you advised. Now I can send email again.

I received plenty of contradictory advice via various forums and your adviser's solution was simplest and entirely effective.

Wish you the best. Thanks again for coming to my rescue.

Paul

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Cannot send e-mail