Mail SMTP (outgoing) does not work after Yosemite upgrade

Thank you so much!! Worked for me! 🙂

Louis XIV wrote:

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 Some have updated and some are using out of date certificates.

Where in the logs on my computer can I find the information that my ISP's server certificates are out of date and being rejected? If I can find this information and send it to them, then maybe I can get them to acknowledge the problem and fix it. If all I do is say, someone said it is your problem, I won't get anywhere.

I gave up on mail and went to PostBox - end of trouble https://www.postbox-inc.com/

I have a similar problem. Since upgrading to ElCapitan I can not access the SMTP outgoing server list to edit it. All I get is a list of the outgoing mail servers that were set up previously. I eliminated all the email accounts and rebooted both the software and computer before rebuilding them but there was no change throughout that process. Any ideas?

Well guys... apple should be easy.. and here one of the probably most used program of OS X is the worse garbage as Mail manager... after tried Thunderbird, MS outlook... and Obviously this ... after tray all solutions posible with makes me lose a lot of hours during the day s ai was trying to find the solution for this stupid STMP issue i finally can say... don´t waste more of your time and choose another program...
I´m using POP Server
I can receive mails but I can't send anything from My iMac, or my Macbook Pro, or mi iPhone 6 or iPad.
after each update is fu..ed again, even if i use the last settings from before update.
With PAssword

Without Password.

re-conf everything again and again.
I see the Future of this program is being forgotten and changed for the same but with different name... like Imail or Ipost...
i`m really disappointed because i will need to use atoner program for my mails...

This really *****...

Hi people.

I've found a working solution, based on the solution in this post.

Tried lots of things, but problem was indeed a crippled plist file.

What solved it was opening the Accounts.plist file situated in:

Users > [username] > Library > Mail > V2 > MailData.

Then what I did was replace the <dict> to </dict> code snippet in this from a WORKING plist file from another machine.

It was this part, and this was the working version here.

Mind you, this is for an SMTP server that should be working with normal password OR TLS authentication with SSL but eventually Apple made it into a MD5 Challenge-Response with SSL on port 587 and that worked.

Replaced my OUTGOINGMAILSERVER below and my EMAILADDRESS and the STRING with these words <

<dict>

<key>AccountName</key>

<string>OUTGOINGMAILSERVER HERE</string>

<key>AccountType</key>

<string>SMTPAccount</string>

<key>AuthenticationScheme</key>

<string>CRAM-MD5</string>

<key>CanonicalEmailAddress</key>

<string>EMAILADDRESS</string>

<key>ConfigureDynamically</key>

<true/>

<key>Hostname</key>

<string>OUTGOINGMAILSERVER</string>

<key>MaxMessageBytes</key>

<integer>100000000</integer>

<key>PortNumber</key>

<integer>587</integer>

<key>SSLEnabled</key>

<string>YES</string>

<key>SecurityLayerType</key>

<integer>2</integer>

<key>ShouldUseAuthentication</key>

<string>YES</string>

<key>UserAllowsInsecureAuthentication</key>

<false/>

<key>Username</key>

<string>EMAILADDRESS</string>

<key>uniqueId</key>

<string>THEREWASASTRINGHERE</string>

</dict>

I have been suffering with this as well since updating to OS X 10.10.3 (I think.) I am now on 10.10.5 and finally giovi73 provided a solution that fixed my issue. To be complete the steps I followed were:

1. Delete my prior SMTP settings
2. Create one SMTP outgoing setting with the configuration recommended by my ISP
3. Close mail preferences
4. Follow giovi73's instructions (quit mail, copy file, edit adding and deleting content)
5. I made one addition to his edits. I changed the ConfigureDynamically flag to 'false'. I believe this corresponds to the checkbox "Automatically detect and maintain account settings". The text for this is:

When I started mail, the test message I had in my outbox immediately sent. I have been able to send additional messages. Tellingly, when I go to 'Edit SMTP Server List...' two things now display differently: 1) The checkbox for "Automatically detect and maintain account settings" is now present but not checked and 2) Dots show in the password field for the authentication using password prompt boxes. Previously this box was blank after I had entered my password. (Note if you make this change and check the SMTP list, be sure to click 'Cancel' to exit without updating the configuration file.)

Hope this helps someone. Thanks to giovi73!

I have El Capitan and there is no longer a Accounts.plist option, however there is a box to check that says allow insecure authentication. Just letting everyone know. So far this seems to be working for me.