Mail SMTP (outgoing) does not work after Yosemite upgrade

If you don't have to do that, don't. Mail should be able to encrypt you username and password as it passes to the SMTP server using SSL. If that fails, then you are stuck with insecure connections.

Most modern server support secure authentication negotiation. This means if you use terminal and the command:

telnet theSMTPServerHostName 25

(replacing theSMTPServerHostName with your server name like smtp.myemailserver.com)

It will reply with a hello (220). You type in: EHLO foo.com and press return and it will tell you what sort of features it offers, including TLS (SSL 3.1)

Here is the response from my server. Notice I used "25" for the port on telnet and I typed that ehlo foo.com and part of the response was "250-STARTTLS" which means when Mail tries to "start TLS" when connecting to my server, it will work ;-) if mail works... It also indicated the type of encryption for passwords that work in the "AUTH" reply.

telnet 127.cumulus:~ munger$ telnet 127.0.0.1 25

Trying 127.0.0.1...

Connected to localhost.

Escape character is '^]'.

220 smtp.redacted.com ESMTP Postfix

ehlo foo.com

250-smtp.redacted.com

250-PIPELINING

250-SIZE 20971520

250-VRFY

250-ETRN

250-AUTH LOGIN PLAIN CRAM-MD5 GSSAPI

250-STARTTLS

250-ENHANCEDSTATUSCODES

250-8BITMIME

250 DSN

The following was my remedy to get Mail SMTP (outgoing) to work with AOL:

Open Mail > Preferences >

In AOL IMAP account under Account Information - Outgoing Mail Server SMTP

Went to Edit SMTP Server List...

Click on the +

Double click Server Name and entered smtp.aol.com

Click Advance tab

Automatically detect...is checked

Port: 25 Use SSL is checked (Not sure if port 25 matters)

Authentication: Password

User Name: Input your user name

Password: Input your password

Click OK

Done

This worked for me.

Good Luck.

I have same issue with Yahoo mail.

after several tries to fix error with keychain store, removing my account from Mail app and restarting my Macbook pro. Issue remains. i cannot SEND email from my Mail App but mails revived.

this trick is helpfull for me:

1. Open Mail preferences

2. Go to Outgoing Mail Server (SMTP) section and click on Edit SMTP server list.

3. In the new windows click on Advanced.

4. in Username section type your user name like 'username@yahoo.com' instead of 'username'

5. renter you password.

6. click OK.

🙂

Good Luck.

To HelicopterJon

I am glad your solution works, I wish I could implement it though because both my Yosemite version and my keyboard are Swiss French, meaning that this sign on your keyboard (next to the left shift key which I can't reproduce) cannot be found anywhere on the keyboard so I can't figure a way to have access to the file you indicate.

When I type "/Library" (without this missing sign before /) in the Finder "Go To" menu, I get the French equivalent "Bibliothèque" that comes up automatically, but Mail is nowhere to be found in this new window, thus I am stuck!

Is there anywhere I could go to to seek help from Apple, after all this is a bug of theirs?

Thank you and good luck to all those experiencing this problem!

Salut, Napoleon25

If you hold down the option key and click on the Go menu in the top-of-the-screen toolbar, you'll see the otherwise hidden Library option appear in the drop-down menu.

Hope that helps.

I emailed Cox. They said use port 25. I tried that for a while, also trying 110 and 995. Changing, saving settings, rebooting, over and over. Noting worked for several days. Last night I tried 995 again, with SSL checked, and !BAM! I'm getting email again. I cannot tell if this is Cox, Apple or a combination but I am tired of going through this exercise 1-2 times a year.

Hi John and thank you for getting back to me with a solution on how to get to that hidden file.

After reading through this thread, I am now less enthusiastic about the proposed insecure connection solution, but I tried once again the trick suggested on Apple article and will see how long that last. Again many thanks for your time!

Where did you go for "Settings" ?Are you referring to IOS or on your Mac?

MY ISP told me to leave "SSL" unchecked

Several times I erased and re entered my password in the Outgoing server part of Mail: Preferences

That helped but I have had to do this two nights in succession

Hope Apple comes up with a solution

I have been working with Apple to get this problem resolved for weeks. They send me to upper level tech support, I sent all kinds of logs to them. Still didn't get it fixed. They called me last week and acknowledged that they were aware of the problem, but currently didn't have a solution. Your solution fixed it! Thank you so much!!

Yep, same. Although Helicopterjohn's fix did not work for me. It is a strange one, not everyone is seeing, so must be a combination of factors. I am with the biggest Telco in Australia but need to reset that email account every three or four days, sometimes more often, yet my other email accounts work fine. Apple Customer Support also informed me that they are aware of the issue, so here's hoping it will be addressed in the next (or first) Yosemite update.

Cheers

Pete

I happened to notice that similar problems with outgoing mail have plagued earlier OS X releases.

Read some threads which pointed out that it is not enough to remove and re enter an account.

The SMTP listings have to be removed and then re-entered with their passwords

Like some others here, I fiddled and fiddled and now mail works.. For a bit

Hopefully Apple will fix soon

I have had the problem with Mail not connecting to one of my ISPs, and could not find a fix other than allowing insecure authentication - which I am very reluctant to do.

Today I was at work, using my MacBook Air, and I noticed that it was connecting OK. So at home I rechecked my iMac, but it was still not connecting. Then I compared the settings in Mail > Preferences > Advanced, and saw that they were different.

- the working account on my MacBook Air: port 995, Use SSL checked

- the failed account on my iMac: port 110, Use SSL unchecked.

I checked the Use SSL box, and the port instantly changed from 110 to 995, and the connection succeeded.

Try this and see whether it helps - it may simply be the case with this particular ISP?

Like many others I have problems with sending and receiving mail. SMTP server shuts down. Have tried all solutions still Doesn't work for me.