Mail SMTP (outgoing) does not work after Yosemite upgrade

I recently upgraded my macbook to Yosemite, and continue to see signs like this that Apple lacks the technical competence to keep up the platform.

For some of us, the fixes described might have worked, but they do not, look at your list of outgoing SMTP servers.

I was surprised to see that Yosemite's Mail client had removed the outgoing SMTP server information for every one of my accounts.

Now, I could manually remove each of my accounts and add them back in, and hope that Yosemite Mail behaves differently,

but I've already spent over an hour on this. I view it as an opportunity to re-evaluate my use of Apple software.

As near as I can tell OSX has been pretty reliable, but all of the instances where I've found myself wasting time under OSX is when I'm using one of the free Apple client software products. They just aren't stable between releases, and my data gets corrupted. My time is much less likely to be wasted now and in the future by moving to a non-Apple software product, free or otherwise. So that's my solution in this case.

Ok Guys.. After trying everything: I quit Mail, went to Key Chain and deleted all of the SMTP entries for AOL in BOTH the "Login" and "ICloud" lists. Then I deleted my AOL account (in "Internet Accounts") and re-added it.

When I reopened Mail I sent a test E-Mail to myself.. the dialogue box immediately popped-up and ask for my AOL Smtp password .. I entered it and voila Mail is now fixed. ....or should I say fixed for NOW 😁

I tried many times, just cannot send mails through in MAIL. As for receiving, most of the time it didn't work, but it did work for 1 or 2 times.

I tried a few ways other users suggested through their web posts, but it seemed that none worked. Helpless. So disappointed to Apple now...

I have tried to follow your instructions but cannot find the key, User allows insecure authentication key.

My outgoing mail does mail but takes several minutes. Not sure if I have the same problem after my upgrade to Yosemite.

Thank you.

So I was having the same problems with Apple Mail app and sending Optimum mail. Optimum's site says to make the outgoing port 587. I changed it to 25 (as per a friend of mine who has Optimum set up on Postbox) and it worked! After calling Cablevision and Apple and ultimately finding this site, that was all the fix that was needed. BTW, Cablevision nor Apple knew what to do! haha

I followed the directions on the site below, but just changed the outgoing port to 25. Hope this helps!

http://optimum.custhelp.com/app/answers/detail/a_id/536

THanks a lot!! I have been several hours trying to fix it!

Thanks, worked like a charm!

Tim: Your recommendation to fix my outgoing email problem was right on the button. When I got to the keychain entry I found that my port setting in the outgoing setup was incorrect so I changed it to the correct one for Verizon.

I would never have thought to go to my keychain settings to fix this. Thank you very much

Harry Bennett (harryb2)

My first attempt at this fix failed, because I made the change under "MailAccounts" and not "DeliveryAccounts." I searched the code for all instances of <key>UserAllowsInsecureAuthentication</key> under "DeliveryAccounts" (I have multiple SMTP accounts), made the changes, and then it worked!

Thank you!

Hi Helicopterjon,

I tried this with the new Yosemite Upgrade but, I still can't send. Did you upgrade to Yosemite 10.10.3? and did you experience the same issue? Did you find a fix?

Thank you for your time.

foodwine

Change "UserAllowsInsecureAuthentication" from false to true?

While I understand allowing insecure authentication might be solving the problem for people, I can't help but think this change means people will be sending their email password insecurely, which would leave people far more vulnerable to having their email accounts hacked. And as so many websites allow password resets via email, the whole idea of reducing security of one's email password seems like a very bad thing to me.

Am I missing something? I'd be happy to hear that I'm wrong! But if I'm correct, I think the reduction in security this "fix" introduces should be clearly explained in the post that everyone is turning to.

This didn't work for me either. My iPhone, iPad, and Mavericks machines are fine and Yosemite is stuck. And it's random when opening mail. Sometimes Connection Doctor shows IMAP working, other times it shows SMTP working, but never both. I am downgrading and I hope Apple fixes this soon.

Deleting and re-adding the smtp list work for me when the comcast smtp server was said to be offline. It was working on one computer but not on another.

Jon -

Is this fix something short-term, until the issue reoccurs again, or is it a more long-term fix for the issue at hand?

Harry,

Was thunderbird a permanent solution for you, or did it fail again?
Thanks and have a great day!