Mail SMTP (outgoing) does not work after Yosemite upgrade

I just upgraded to Yosemite and had the same SMTP connection problem. I went into settings and found that my Mac Mail program was regarding my Lunarpages server as "not trusted". I clicked on the box to "always trust" the server and that solved the problem.

Where is this option Bulldog?

I wish I could tell you. I believe I got there from the window giving the error message. The problem has to do with Yosemite not recognizing SSL certificates. Just look around when you get the error message and look for the advanced tab in your mail accounts settings. Somewhere you're going to find something indicating that Mail is does not trust your server. Wish I could help more, but it's there.

Update: From the error message click on "show certificate" and you'll see a box to click called "always trust".

Update: From the error message click on "show certificate" and you'll see a box to click called "always trust".

Update: From the error message click on "show certificate" and you'll see a box to click called "always trust".

had a similar issue also, everything just went to outgoing mail folder. It had to do with outgoing smpt lost or forgot the password. Reentered the password and the mail in the outgoing mail folder was sent.

Tried all the suggested solutions so far but no joy. I deleted the same account completely off my iPhone and set it back up again. It automatically detected the settings and no problems with sending mail. Yosemite has broken something !!

Hi

not to sure if that works for everyone, So far it did for me. The same issue was when Mavericks game out . I had issues with two of my smtp accounts. After the upgrade Yosemite did the same thing as before with Maverick it changed the smtp settings to automatic detect settings in the advanced menu of your edit smtp server list. so just uncheck that setting. close down mail and open it up again and it did work for me. In the past the automatic setting game on by it self but so far it is off. You need to give the manual port number like 25 or 578 or what ever your provider gives you.

so for once more go to Mail Preferences choose accounts go to the account in question, make sure you on the first tab accunt information go to outgoing mail server , then go to edit Smtp server list (double arrows) and go to the advanced tap and uncheck the automatic settings make sure you have a port number below

hope that helps

Hi

I have the opposite problem. Works on my MBP (early 2013) but NOT on my Mac (Late 2011)

Thats a good answer, but for me is not the solution.

I had done all this steps and the problem still with outgoing messages.

When i go to "inspector connection" all the accounts are successfully connected.

But the SMTP of mi personal domain cannot connect.

Sorry for mi rustic english....

not to sure what the reason can be sorry do not really have an answer. Maybe a restart helps as said the most important part was to close out Mail after the change and then open it again and it seemed to work on my side .

hope you guys can figure it out as I know it can be very annoying

regards

Bernd

I have this same type problem. I believe I have my account set up correctly, and have an SMTP Log which shows what the failure is. If I can manage to insert it, I will. Happy day: lots of room taken up, but a short clip from the log. Note that after connecting, he reads the first message (220) which tells him some info about my ISP's server. Then he writes an EHLO to the server. He reads the next message from the server, and gets message (250) which tells him more about the server characteristics I think. But then, he writes and EHLO again, and bang, he reads the next message, which is

503: Saw HELO/EHLO already. That is quitting time, and he is now OFFLINE.

Now, I left my work with IBM about 10 years ago, am 81 yrs old, and I have not had to debug any Apple code over the years, so I need to know if I can still access the Apple Knowledge Base info, how I might talk to a developer or tech guru, or if anything else that I could do to technical help.

CONNECTED Oct 20 16:40:48.124 [kCFStreamSocketSecurityLevelNone] -- host:smtp.everyone.net -- port:25 -- socket:0x6000004bbc00 -- thread:0x60800107e4c0

READ Oct 20 16:40:48.164 [kCFStreamSocketSecurityLevelNone] -- host:smtp.everyone.net -- port:25 -- socket:0x6000004bbc00 -- thread:0x60800107e4c0

220 dm0201.mta.everyone.net ESMTP EON-AUTHRELAY2

WROTE Oct 20 16:40:48.461 [kCFStreamSocketSecurityLevelNone] -- host:smtp.everyone.net -- port:25 -- socket:0x6000004bbc00 -- thread:0x60800107e4c0

EHLO [10.0.1.6]

READ Oct 20 16:40:48.515 [kCFStreamSocketSecurityLevelNone] -- host:smtp.everyone.net -- port:25 -- socket:0x6000004bbc00 -- thread:0x60800107e4c0

250-dm0201.mta.everyone.net

250-PIPELINING

250-SIZE 50000000

250-AUTH PLAIN LOGIN

250-AUTH=LOGIN

250 8BITMIME

WROTE Oct 20 16:40:48.515 [kCFStreamSocketSecurityLevelNone] -- host:smtp.everyone.net -- port:25 -- socket:0x6000004bbc00 -- thread:0x60800107e4c0

EHLO [10.0.1.6]

READ Oct 20 16:40:48.567 [kCFStreamSocketSecurityLevelNone] -- host:smtp.everyone.net -- port:25 -- socket:0x6000004bbc00 -- thread:0x60800107e4c0

503 Saw HELO/EHLO already