flemminggitte
Level 1 (1 points)

Q: Mail SMTP (outgoing) does not work after Yosemite upgrade

I have just updated Yosemite on my Mac and MacBook Air and the outgoing mails cannot be sent - the SMTP-connection fails.

It worked fully Ok few seconds before the upgrade was started.

 

So, I wonder if anyone or Apple can help on getting the Outgoing mails to work again.

iMac (27-inch Mid 2010), iOS 8.0.2

Posted on Oct 19, 2014 9:23 AM

by HelicopterJon,Solvedanswer
HelicopterJon HelicopterJon
Level 1 (15 points)
A:

Quit mail

Open up Finder

In the Finder menu bar select Go > Go to folder

type in ~/Library and click Go (on my kb the "~" is next to the left shift key)

Open the folder Mail

Open the folder V2

Open the folder MailData

Double click to open Accounts.plist (should open in TextEdit)

Find the block of data that contains the offending mail account

Find the line within this block that says <key>UserAllowsInsecureAuthentication</key>

Change the line below this from <false/> to <true/>

Quit TextEdit

Restart mail

Posted on Oct 22, 2014 9:03 AM

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flemminggitte

Q: Mail SMTP (outgoing) does not work after Yosemite upgrade

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  • by Bulldog Investigations,

    Bulldog Investigations Bulldog Investigations Oct 20, 2014 9:36 AM in response to nrg162
    Level 1 (0 points)
    Oct 20, 2014 9:36 AM in response to nrg162

    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.

  • by Bulldog Investigations,

    Bulldog Investigations Bulldog Investigations Oct 20, 2014 9:39 AM in response to Varkias42
    Level 1 (0 points)
    Oct 20, 2014 9:39 AM in response to Varkias42

    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.

  • by Chepoka,

    Chepoka Chepoka Oct 20, 2014 10:02 AM in response to Bulldog Investigations
    Level 1 (0 points)
    Oct 20, 2014 10:02 AM in response to Bulldog Investigations

    Where is this option Bulldog?

  • by Bulldog Investigations,

    Bulldog Investigations Bulldog Investigations Oct 20, 2014 10:09 AM in response to Chepoka
    Level 1 (0 points)
    Oct 20, 2014 10:09 AM in response to Chepoka

    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.

  • by Bulldog Investigations,

    Bulldog Investigations Bulldog Investigations Oct 20, 2014 10:27 AM in response to Chepoka
    Level 1 (0 points)
    Oct 20, 2014 10:27 AM in response to Chepoka

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

  • by Bulldog Investigations,

    Bulldog Investigations Bulldog Investigations Oct 20, 2014 10:28 AM in response to flemminggitte
    Level 1 (0 points)
    Oct 20, 2014 10:28 AM in response to flemminggitte

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

  • by Bulldog Investigations,

    Bulldog Investigations Bulldog Investigations Oct 20, 2014 10:29 AM in response to flemminggitte
    Level 1 (0 points)
    Oct 20, 2014 10:29 AM in response to flemminggitte

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

  • by Snagged,

    Snagged Snagged Oct 20, 2014 10:43 AM in response to flemminggitte
    Level 1 (0 points)
    Oct 20, 2014 10:43 AM in response to flemminggitte

    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.

  • by HelicopterJon,

    HelicopterJon HelicopterJon Oct 20, 2014 10:54 AM in response to flemminggitte
    Level 1 (15 points)
    Oct 20, 2014 10:54 AM in response to flemminggitte

    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 !!

  • by flemminggitte,

    flemminggitte flemminggitte Oct 20, 2014 11:49 AM in response to Bulldog Investigations
    Level 1 (1 points)
    Oct 20, 2014 11:49 AM in response to Bulldog Investigations

    Where do you find "show certificate" - I do not get this option at all when I try to send a message that fails.

    I have tried all so far suggested solutions and NONE of them works.

     

    I have a Swisscom/Bluewin email account - if that should help at all for a solution

  • by racb,

    racb racb Oct 20, 2014 12:16 PM in response to flemminggitte
    Level 1 (0 points)
    Oct 20, 2014 12:16 PM in response to flemminggitte

    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

  • by flemminggitte,

    flemminggitte flemminggitte Oct 20, 2014 1:13 PM in response to racb
    Level 1 (1 points)
    Oct 20, 2014 1:13 PM in response to racb

    Hi racb,

    It works for my Mac but I cannot get it to work on my MacBook Air 11" late 2010.

     

    I have checked and I have exactly the same account settings on the 2 Macs - any idea what is wrong on the MacBook Air.

  • by HelicopterJon,

    HelicopterJon HelicopterJon Oct 20, 2014 2:00 PM in response to flemminggitte
    Level 1 (15 points)
    Oct 20, 2014 2:00 PM in response to flemminggitte

    Hi

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

  • by Chepoka,

    Chepoka Chepoka Oct 20, 2014 2:22 PM in response to racb
    Level 1 (0 points)
    Oct 20, 2014 2:22 PM in response to racb

    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....

     

    Captura de pantalla 2014-10-20 a las 18.14.02.png

  • by racb,

    racb racb Oct 20, 2014 2:59 PM in response to flemminggitte
    Level 1 (0 points)
    Oct 20, 2014 2:59 PM in response to flemminggitte

    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

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