Mail SMTP (outgoing) does not work after Yosemite upgrade

I also could not send outgoing via comcast smtp, though I could get incoming. I kept getting the message that the comcast outgoing server was offline. when I tried to "edit smtp server", I could type in my password,but it wouldn't stay there (it would be gone the next time I checked, and the server was still reading "offline").

This helped me. I had two email accounts on Mac Mail. One was my comcast account, the other was my gmail account. i simply deleted my gmail account (Mail>Preferences>Accounts, then click on Google IMAP account and delete it by clicking the "-" on the bottom of the accounts list. Confirm you want to delete it, close and re-open mail, then try to send. Once successful, you can re-add your google mail account.

Thanks deleting gmail helped - soon much time wasted before I found you guys though (grrr apple clearly only want us to use their mail!)

Thanks

Thanks. Worked for me.

Hi everybody,

first of all, I want to thank you for your help.

However, none of the suggestions posted worked for me 😟

I spent the whole night making several attempts by following your suggestions, but unfortunately I could not send mail.

I use an iMac and updated Yosemite to version 10.10.5: unfortunately I did not know about the problem with the SMTP authentication, otherwise I would not have made the update.

In the end, I was thinking to restore the iMac from a TimeMachine backup because I didn't knew what to do anymore.

But first I wanted to try last possibility and it works fine for me: I hope it will be helpful to those who still have not solved the problem.

That's exactly what I did:

1. I configured the mail and the SMTP server on a MacBook with Yosemite 10.10.2 and everything worked properly.

2. Then I tried this on my iMac with Yosemite 10.10.5 (from which I could not send mail):

- Quit out of the Mail app

- From the OS X Finder, hit Command + Shift + G and enter the following path:

~ / Library / Mail / V2 / maildata /

- There is a file called "Accounts.plist" and I made a copy of it to my desktop (it's important, do not forget to do this)

- Open, in the MailData folder, the file named "Accounts.plist" with TextEdit

3. I compared the section "<key> DeliveryAccounts </ key>" (it is at the beginning of the file "Accounts.plist") with the same file of the MacBook (which provide email working properly) and I saw that there were differences.

I made several attempts and at the end I was able to send mail correctly from my iMac with Yosemite 10.10.5, without downgrading to 10.10.2.

Please, check the png file attached for instructions.

I think it's a bug and hope that Apple will fix it as soon as possible. It was very frustrating....

Hope my solution will be helpful to you.

Bye,

Giovi

Two items of note on this problem. One you change one checkbox in the SMTP server config, as seen below. Check the checkbox for allow insecure authentication.

Secondly, make sure your email hosting service whitelists your IP. Send them an email with your IP, which you can Google search for, or go to http://whatismyipaddress.com/

(You might be able to whitelist it yourself if you have Control Panel access to the hosting server. This is a tip to web hosts, not the typical end user.)

Dear HelicopterJon,

I too have the same issue. I did as per your instruction but still the issue is same.

Can you pliz suggest me if there is anything more to solve this issue permanently ?

Regards

Puskar

Dear all, one of my four e-mail accounts started malfunctioning a couple of weeks ago, I could receive but not send mail through that account. Maybe it was as I updated to 10.10.5, I'm not sure. I have had the same problem about a year ago and then had to reinstall the account in order to fix the problem. There was no problem sending e-mail through the offending account on my iPhone and iPad, with identical smtp settings.

This time I tried all the solutions suggested in this thread, editing p-list, checking and unchecking boxes, etc. Nothing worked. What eventually seemed to have fixed the problem was that I deleted the malfunctioning smtp server in the list of smtp servers and created a new one (different name, same settings).

It seems there is no solution that works for everyone, very strange ...

/ Thomas

Solution for AOL accounts SMTP in Yosemite

I'm afraid I tried various solutions here for the problem with my AOL accounts, and none seemed to do the trick. However I discovered elsewhere that changing the DNS settings to Google's 8.8.8.8 fixed it. So I changed to those and also had Mail's SMTP settings set as below.

Autodetect settings: OFF

SSL ON at 465

Authentication: Password

Allow insecure authentication: OFF

To change DNS server settings:

System Preferences > Network . Choose your active (green) connection, click Advanced > DNS. Click [+] at bottom left and enter 8.8.8.8. Click OK on that screen and then click Apply on the underlying one.

You can check the status in Mail's Connection Doctor. Should be all green this time :-)

Quit and relaunch Mail before testing though—I found that my text mail stuck until I did so.

Guy

Since this hasn't been universally resolved with 10.10.5, I thought I might ask this question: Has any of the developers on this thread examined this issue under 10.11, El Capitan?

While Apple seems to have indicated that 'some' services were fixed with 10.10.5 in the Mail app, there are still issues. Have they perhaps decided that they'll have a bigger, more fully encompassing, fix in the new version, 10.11? Has anyone had the chance to check?

Finally. Thanks. Seems to be working now.

Thanks for the creative solution, but Yikes. Shutting off security to get it working is like shutting off the Wi-Fi security on your home gateway instead of figuring out why your device won't connect properly *and* securely.

I use Comcast and struggled setting up IMAP email since the default apple/Comcast handshaking don't seem to work. I tried deleting the keystore entries, etc. etc. What worked for me was to make sure the INCOMING and OUTGOING PORTS were configured. I was really surprised by this since the client/server are supposed to work this stuff out, I thought. I followed config details from this post:

http://customer.xfinity.com/help-and-support/internet/email-client-programs-with -xfinity-email/

Here's what worked for me.

• Open Mail
• Open activity window for debugging: MENU > Window > Activity (little window pops up showing Mac <-->server communications)
• Delete any existing troubled Comcast account on your mac (select Comcast account, click "-")
• Add a fresh "Comcast" account.
• ====> MENU > Mail > Preferences... (see popup. For some reason, this window is more detailed than "Accounts")
• In the resulting window, add your email address and password as expected.
• The system will attempt to communicate with server. You need to override the port settings
• ====> INCOMING: On the "Preferences" window that popped up, click Comcast account, then click the white "advanced" tab. Change the "port" to "993" and make sure "Use SSL" is Checked". My "IMAP Path Prefix" is blank.
• ====> OUTGOING: On the "Preferences" window that popped up, click Comcast account, then click the white "Account Information" tab. Click the "outgoing mail server (SMTP)" pulldown and select the option "Edit SMTP Server List...". This will pop up another window. On this window, enter port "467", and make sure "use SSL" is checked. Click OK in the popup.
• You should now be in the Preferences... popup on the "Accounts" tab.
• Oddly, my changes didn't save until I clicked on ANOTHER account (e.g. my gmail account) and the system prompted me to "Save" or "Discard". Save your settings.
• That should be it. The only drawback is that my Comcast account proceeded to download thousands of messages going back years. I could find no way to force it to only sync back a few months. At least with the "Activity" window opened, you can see the status of messages being downloaded.

Note, if you didn't enter your password in the config, it may ask you to enter it upon first check.

Good luck, y'all!

Thanks for the information on your xfinity fix. This is a variant of everyone's problem, either the functionality of "Automatically detect and maintain account settings" and/or the something in the sending of emails causes the SMTP password to be lost. I too have been in this boat since I upgraded from 10.10.3 to 10.10.5. If I had known of this issue I would not have done the upgrade. Does anyone know how we get some attention from Apple support on this?

THANK YOU! I just spent two days and over 6 hours trying to fix that. That did for me.

This was the solution that worked for me. I had been having issues not only with SMTP but with Mail saving preferences / passwords in Mail Accounts under Preferences as well as in Internet Accounts (not SMTP, but passwords, etc., there). Other approaches had not solved the issue, but deleting all items in Keychain, then shutting down and starting up again, worked

The reason everyone is having trouble with their outgoing Yosemite and El Capitan email is because the new OS requires updated certificates from the servers. Some have updated and some are using out of date certificates.