RoshBaby2

Q: Why do my SMTP/IMAP/POP servers keep going offline in OS X Yosemite Mail app?

I have a MacBook Pro from summer of 2011 and just upgraded to OS X Yosemite. Now my Mail app keeps taking the servers offline randomly and keeps it can't reconnect. I can fix it by quitting the app, shutting my computer, and then opening it and restarting the app, but if someone has a permanent fix that would be much appreciated.

 

I've gone into the accounts and made sure the information was correct, reentered it, etc. And I think the port numbers are correct (I changed them but that didn't help anything). I've also repaired my Keychain because that seemed to cause problems in previous OS versions.

 

Everything else on my computer still logs in and accepts the passwords (so far), it's just the Mail app that broke. And it was working great until I upgraded to Yosemite.

 

Thanks!

MacBook Pro, OS X Yosemite (10.10)

Posted on Oct 21, 2014 8:04 AM

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Q: Why do my SMTP/IMAP/POP servers keep going offline in OS X Yosemite Mail app?

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  • by ECM G,

    ECM G ECM G Jun 30, 2015 2:39 AM in response to Kenny Millar
    Level 1 (0 points)
    Jun 30, 2015 2:39 AM in response to Kenny Millar

    Reports sent already. If Thunderbird works I will stick with it though, the issue has been going on for a bit too long for me to be comfortable with Mail as I'll always feel worried that there is something wrong with the system.

  • by Kenny Millar,

    Kenny Millar Kenny Millar Jun 30, 2015 2:44 AM in response to ECM G
    Level 2 (310 points)
    Jun 30, 2015 2:44 AM in response to ECM G

    Brill :-)

     

    You are not wrong here - mail has had a troubled history and many people have lost faith in it.

    The upshot of this is that it has let things like Fox Mail and Dropbox Mail get a foothold.

     

    The Maill.app team at apple obviously missed out on the "It Just Works" lecture on induction day.

  • by ECM G,

    ECM G ECM G Jun 30, 2015 2:46 AM in response to Kenny Millar
    Level 1 (0 points)
    Jun 30, 2015 2:46 AM in response to Kenny Millar

    Hahaha yes I never thought I would get excited about work e-mails arriving at their intended destination! Or being sent without issues.

  • by Bob Jacobson,

    Bob Jacobson Bob Jacobson Jul 9, 2015 5:02 PM in response to Kenny Millar
    Level 1 (124 points)
    Jul 9, 2015 5:02 PM in response to Kenny Millar

    Kenny Millar wrote:

     

    It seems that Apple have been making changes under the hood to the SSL code.

    For example, OpenSSL has been deprecated and replaced with their own implementation.

    By far the best thing you can do is report this as a bug at bugreport.apple.com - you may not get a response, but it WILL add weight to the issue.

    The more people report the issue there, the more attention it will get.

     

    In your report be courteous and professional, stick to reporting the facts of the issue, and refrain from making any personal comments. Just describe the issue in detail, and include screen shots of mail's "connection doctor".

     

    In the meantime, you could try a webmail solution, if your mail provider offers it, or use another mail client such as Fox Mail.

     

    I did a search of the Bug Report webpage using "Apple Mail" and "smtp" and got nada.

  • by Bob Jacobson,

    Bob Jacobson Bob Jacobson Jul 9, 2015 5:43 PM in response to RoshBaby2
    Level 1 (124 points)
    Jul 9, 2015 5:43 PM in response to RoshBaby2

    My 2012 Macbook Pro hasn't had these problems, but my partner's 2010 iMac is so plagued when she tries to use her SMTP function with Cox Cable.

     

    Using Yosemite 10.10.3, her IMAP access to Cox worked faultlessly.  She could easily receive Cox email transferred from Cox's Webmail page.  (She still can.  IMAP is no problem.)

     

    But her Send Mail authentication method was constantly being changed to MD5 Challenge Response, rather than Password, which resulted in her going "Offline" each time.  We found that once we changed the authentication method from MD5 Challenge Response to Password, and entered the proper password, she stayed online and could easily send email via Cox.net.  Annoying but workable.

     

    That was under 10.10.3.  Yosemite 10.10.14 has opened a whole new can of worms.  Sorry I didn't know about it before I installed 10.10.4!

     

    My partner can no longer use Apple Mail to send mail via Cox.  She enters her password, exits the SMTP editor, and voila! ... she's "Offline" again, while back in the SMTP editor, the password has disappeared.  However, when I replicated her account on my MBP, everything worked fine. We're still not clear why her iMac has these problems and my MBP doesn't, but it's probably not a Cox issue.

     

    Cox, however, is taking it seriously and escalating our trouble ticket to a higher-tier. The agent said, "We've heard it before."  Probably nothing they can do about it, but we're glad they're trying.  None of the solutions proposed in this forum so far has worked, so I'm setting her up with direct access to Cox's Webmail page via a Chrome bookmark.

     

    Fortunately, my partner's Apple Mail still accesses IMAP (incoming mail) from Cox, so after she reads it, she can reply using another ISP's mailserver. In the end, she may prefer to switch all of her email needs to another ISP she favors.  Which is why Cox is concerned.

     

    We wish we could say the same for Apple. Typically, it's quiet on the issue, hoping I suppose that if not enough people are crippled in this fashion, it can ride out the complaints until OS 10.10.15 or 11.0 become available ... and then do the same thing all over again.

     

    Apple Mail is regularly embellished -- Notifications, new layout, etc. -- but not mechanically improved upon.  I'm now looking into Thunderbird and Air Mail, each of which has peculiarities but at least work.

     

    PS I would seriously NOT disable Use Secure Authentication or use an unsecured port like 25.  That's an open invitation to a crook to highjack your email account.

     

     


  • by Kenny Millar,

    Kenny Millar Kenny Millar Jul 10, 2015 2:56 AM in response to Bob Jacobson
    Level 2 (310 points)
    Jul 10, 2015 2:56 AM in response to Bob Jacobson

    In the latest Mail apple no longer support SMTP Servers with less than 1024 Bit encryption.

    You either have to badger your ISP to upgrade to 1024 Bit. or you have to live without encryption (if your ISP Supports it).

  • by LShark,Helpful

    LShark LShark Jul 11, 2015 4:58 PM in response to RoshBaby2
    Level 1 (9 points)
    Jul 11, 2015 4:58 PM in response to RoshBaby2

    I've had a similar problem, only with gmail, and it started with the 10.10.4 update.  I had to do several things to get it all sorted out:

    1. Refreshed the keychain entries - this solved some problems, but not all
      1. Keychain firstaid repair - didn't find any problems.
      2. Deleted all gmail keychain entries, for both imap and smtp.
      3. Re-entered credentials in mailbox settings and smtp server settings.
    2. Enabled Automatically detect and maintain account settings (under Advanced, for each gmail account in Accounts) - this helped for an hour or so, then stopped working again.
    3. Changed smtp port settings - this finally fixed the problem for good (so far...)
      • Created a separate server in the smtp list for each account, and set each account to use only its specified smtp server.
      • For each gmail account, configured as follows:
        • Server Name:  -  smtp.gmail.com (per Google, if you use a Mac and the server name is smtp.gmail.com:<username>@gmail.com remove the colon and username).
        • Automatically detect and maintain account settings - ENabled
        • Port: - 465 (25 theoretically works too, but not for me)*; use SSL - ENabled.
        • TLS Certificate: None (if you use TLS, port should be 587, per Google).
        • Allow insecure authentication - DISabled.
        • User Name: - <myname>@gmail.com (entire address is required).

    *I figured out that part of the problem was that the port settings kept reverting to 587, even after I manually set them to 465.  I finally got them to stick by editing and saving each SMTP server in the list before editing another; if I edited them all and then saved (clicked OK), the settings would revert to 587.  Since the best settings are potentially different for different networks/ISP's, I wasn't sure what to use.  At first, I thought the port reversion was happening because the setting should be 587, but it didn't work.


    I tested by telneting to smtp.gmail.com on each of the ports in question (25, 465 and 587).  I stuck with 465 because of the responses I got.  25 timed out.  587 connected, but then wouldn't disconnect, even with a manual break.  465 connected and disconnected as requested:

    term-telnet.png

  • by mbrun,

    mbrun mbrun Jul 12, 2015 4:49 PM in response to LShark
    Level 1 (110 points)
    Jul 12, 2015 4:49 PM in response to LShark

    Thanks LShark, mine is working now after getting the offline message following an update to 10.10.4. This really frustrates me since I also lost all my outgoing mail servers when I did the 10.10.3 update. They just disappeared.

    I tried several times to re-save my password and a few other things which failed to remedy the offline message from gmail. Following your instructions seems to have fixed it. I set my port to 465. Hopefully this will stick.

  • by LShark,

    LShark LShark Jul 12, 2015 7:40 PM in response to mbrun
    Level 1 (9 points)
    Jul 12, 2015 7:40 PM in response to mbrun

    mbrun - So glad it helped!

  • by mariotheplumber,

    mariotheplumber mariotheplumber Jul 20, 2015 4:19 AM in response to RoshBaby2
    Level 1 (53 points)
    Apple TV
    Jul 20, 2015 4:19 AM in response to RoshBaby2

    seems like iPad also suffering from same issue since latest iOS update.

  • by Kenny Millar,

    Kenny Millar Kenny Millar Jul 20, 2015 4:21 AM in response to mariotheplumber
    Level 2 (310 points)
    Jul 20, 2015 4:21 AM in response to mariotheplumber

    Yes.

     

    I think the correct solution here is to pressure your ISP to support 1024 Bit encryption (at least).

  • by mariotheplumber,

    mariotheplumber mariotheplumber Jul 21, 2015 4:16 AM in response to Kenny Millar
    Level 1 (53 points)
    Apple TV
    Jul 21, 2015 4:16 AM in response to Kenny Millar

    Don't quite understand this issue.

     

    Currently everything is working for me after some 'playing' araound...

     

    1) deleted all my email accounts from within Mail App

    2) reinstalled manually all accounts then from within Mail App.

    3) Settings>Internet Accounts and deleted all Mail accounts here

    4) Settings>Internet Account and reinstalled them manually

    5) back to Mail App and deleted all mail accounts

    6) keychain and made sure that there wer no items related to Mail accounts or iCloud

    7) back to Mail App and reinstalled manually...

     

    Everything works again for now. This took 3 hours and was an ****, but I appear to be able to end and receive mail on all accounts without any error messages. Nothing else has changed.

     

    ...Coincidentally, during this process I did notice that OSX kept changing the order of the mail accounts each time I opened the Mail App (it put iCloud and other providers accounts ahead of my 'other' accounts.) Finally though, after deleting all keychain items it appears to have stopped doing this and nows leaves them in the order that I determined.

  • by Henry-In-FL,

    Henry-In-FL Henry-In-FL Jul 21, 2015 7:00 AM in response to LShark
    Level 1 (5 points)
    Servers Enterprise
    Jul 21, 2015 7:00 AM in response to LShark

    In my case SMTP are the one that go offline frequently due to the SSL setting being on. This happens in Gmail and other IMAP accounts. If I turn off the the SSL check box <OR> delete the password from the settings in the dialog box, then they stay on line. So, it doesn't have anything to do with getting a server response (though thanks for the terminal log in check. It's using the server in SSL vs. non-SSL configs that affects Mail.

     

    Have any thoughts on how to check and replicate this issue? Like I said for me, it's flaky/intermittent.

  • by Henry-In-FL,

    Henry-In-FL Henry-In-FL Jul 21, 2015 7:15 AM in response to Henry-In-FL
    Level 1 (5 points)
    Servers Enterprise
    Jul 21, 2015 7:15 AM in response to Henry-In-FL

    I think that the issue is the SSL certificate validation on the server. The SSL security doesn't have a current certificate.

  • by Provisioncolor,

    Provisioncolor Provisioncolor Jul 25, 2015 5:35 PM in response to LShark
    Level 1 (0 points)
    Jul 25, 2015 5:35 PM in response to LShark

    Thanks LShark.  After trying many of the other suggestions, this worked for me.  I had multiple Keychain entries for the same account, so I'm guessing that may have had something to do with it.

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