Mail SMTP (outgoing) does not work after Yosemite upgrade

I used to be in the hosting business and use my own dedicated machines for past 15+ years. First major issue I've had with iMail and a Mac...and must admit this one is a stumper at the moment. I've tried many of the suggestions here, but nothing working. I'm going to try creating a new hosting account so I know I have nothing stored on machine and see what happens.

Email has worked great up until Yosemite update. Also a tad discouraging to see all the other issues being reported since Yosemite update.

Time to dig in 😕

yosemeti email issues, email issue, smtp not working, outbound email not working

I'm seeing the same-thing...same settings on my iPhone work, but not on Macbook since Yosemite upgrade.

Although I solved my issue after a combination of many of the proposals here (editing the Mail internal file, editing the accounts settings, rebooting, etc...unfortunately, I do not know which one was the correct one, or all), I sent an email message to Tim Cook and Phil Schiller at Apple (yes! I have their emails) and forwarded some of the complaints from the forum. I got a call from Apple Corporate Relations (on behalf of Tim Cook) within 24 hours to see what was my issue. They told me that if users have issues with Yosemite, and since it is a new product, Apple Customer Care will support the customers and users are encouraged to call over the phone at no charge (Apple does not monitor the forums).

Another suggestion is to post the issue on Twitter and naming Tim Cook on the message. That will get the attention of people.

Hope this helps

This was not successful on my I-Mac.

This method failed also for me.

helsunOct 28, 2014 5:01 PM

For all of you having a problem sending mail in the Yosemite, please follow this. I am not computer savvy, yet I figured this out from another great website.

Go to: Mail, Preferences, Account Information. Highlight your email account. Go to Outgoing Mail Server SMTP. Click on the little down arrow and it will say: Edit SMPT server list. (Make sure the correct email account is checked). Click on the Advanced tab. Check: Automatically detect and maintain account settings and Use SSL. Then, last step, type in your user name and password again, even if you think its correct. Mine was correct but I retyped both again. Last step, click OK. I was immediately able to send mail. Hope this works for you.

I'm no wiz kid but this worked for me........

Open mail and go to the tool bar and click on Window, then click on Connection Doctor. Double click on SMTP if it shows that it failed to connect.

Re enter your password when window pops up in the advance tab. Click ok and close everything. Open mail and send away!

What finally worked for me, I kept SSL checked but I double checked the port number. The port number was for the port for non-SSL so I changed the port number to the correct one and it now works. I did uncheck automatically check and maintain account settings.

Good luck.

That was it. HelicopterJon, nice going. Apparently the code between the SMTP setting and the storage using prefs on disk is broken in either Mail or in the system.

I am getting all manner of problems with authenticating to services that I had previously working even under the betas of Yosemite. This solved one big one.

Thanks again!

I was a Microsoft-only bigot until VISTA. I switched to an iMac. I enjoyed many years afterward of turn it on, use it, enjoy, play with it some, but mostly it works and you don't have to chase 4-5-6 tiered settings down in some configuration menu. I spent several nights this week trying to figure out why my port kept resetting from 25 (suggested by Cox) to 110, 995, 985 or m-o-u-s-e. I never noticed the 'automagic' 'detect email settings' check boxes. I didn't dig thru this many page (unhelpful) discussion, I googled it and yelled at Cox. Didn't know they now offer a port 25 for mac users. Also didn't know Apple decided to default to YES on two 'automagically' detect port settings on my e-mail. Those kept re-setting my email back to 110, 985, 995, or m-o-u-s-e every time I restarted. Still prefer Apple, but fear they are jumping down the same rabbit hole that drove me away from Microsoft.

This worked for me on my colleagues Mac, thanks!

I have tried everything mentioned above. Helicopter John's remedy worked for awhile, but my problem is off and on. For no given reason it will just stop working again. And then 5 - 45 minutes later it will work again.

I have several emails accounts within my mac mail and ALL of the others are fine. I just seem to be having an issue with the address of which my server is hosted at hostgator. Hostgator claims the OSX update is the problem, and therefore an Apple problem - However, why are ALL my other addresses working perfectly with the exception of my hostgator emails?

This is SO frustrating!!! Does anyone know if I restore from time machine prior to the upgrade, if it will go back to the previous operating system?

Any advice is greatly appreciated.

Cheers,

Lilly

I spoke too soon. Turning off the 'auto-check' for mail server settings worked last night. Tonight I'm unable to send OR receive emails in my Cox account. At this point it appears there is some success in changing 'allow insecure login' from false to true... but (no offense intended) I'm not comfortable with making that change. I would prefer not to allow insecure login to my email account. I'd like to hear a better answer, or at least a confirming response from Apple, who caused this issue with the Yosemite update, and has caused similar problems with my email with previous updates. I prefer a local mail client to webmail but Apple seems to be forcing me over to browser-mail by consistently breaking Apple Mail with most updates.

Did you check the port number to make sure it's correct? I had that issue. The port number was incorrect, it was the non-security port when SSL was checked. (I never changed these settings, I guess Yosemite did?) I changed the port number for SSL enabled and kept SSL checked. See if that helps.

I finally got Mail to work on both my I-Mac and Macbook Air by checking "Allow insecure authentication but that scares me a little. How likely is that to be a problem?