eike.hoffmann

Q: 10.10.4 Mail SMTP problem

Hi,

 

I know, that there are other discussions regarding Apple Mail not sending mails via SMTP. Most of these SMTP-servers do not use a strong DH key (logjam). But my problem is different.

 

I'm using a self operated mail server with dovecot (and dovecot SALS) and postfix. The server already uses strong DH keys and strong encryption. TLSv1.0 is available, but not v1.1 or higher.

 

Actually I had no problems before 10.10.4. The problems started after I upgraded to 10.10.4.

 

I use a payed Google Apps account in combination with my own SMTP server for sending mails. So Google Apps IMAP for incoming, my own SMTP server for sending mails.

 

I tried changing the configuration, but it simply does not work. Apple Mail connects, but sends no password.

 

The servers mail.log says simply:

 

Jul 13 10:09:21 aldur postfix/smtpd[28176]: warning: unknown[x.x.x.x]: SASL LOGIN authentication aborted


The connection log says (garion is my MacBook):


Jul 13 10:09:47 garion Mail[1346] <Debug>: Connected: <MFSMTPConnection: 0x60000057a580> (Connected) account: A{SMTP - 534CDE8D-59E7-4698-8A0E-ABF14A273AB5}

  hostname: hostname.domain.de, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1_0

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] >> EHLO  (19 additional bytes)

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-hostname.domain.de

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-PIPELINING

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-SIZE 110000000

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-VRF

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-ETRN

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-AUTH PLAIN LOGIN

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-AUTH=PLAIN LOGIN

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-ENHANCEDSTATUSCODES

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250-8BITMIME

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 250 DSN

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] >> AUTH  (5 additional bytes)

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 334  (12 additional bytes)

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] >>  (12 additional bytes)

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 334  (12 additional bytes)

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] >> * (0 additional bytes)

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 501 5.7.0  (22 additional bytes)

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] >> QUIT (0 additional bytes)

Jul 13 10:09:47 garion Mail[1346] <Debug>: [0x60000057a580] << 220  (28 additional bytes)

 

Interessting are the bold lines. Apple Mail successfully connects to my SMTP server via TLSv1.0. It sends the EHLO and starts AUTH (first bold line). Thre server responds "give my your login name" (second bold line). Mail responds "here it is" (third bold line, 12 Byte BASE64 encoded login name). Then servers asks "ok, now give me your password" (fourth bold line). And Apple Mail respons with 0 bytes, so an empty password.

 

But the password is correctly set. It's stored in keychain, too.

 

My first solution was to use Airmail 2 and wait until a solution may be discovered (I upgraded to 10.10.4 when it was released). But up to now, there is no fix...

 

The problem is clearly Apple Mail, because other clients do not have any problems. Even the local postfix on my MacBook works. I configured the local postfix on my MacBook to forward all e-mails to my SMTP server, using PLAIN authentication. This works without problems.

 

Currently I configured Apple Mail to send mails through the local postfix (which forwards them to my SMTP server...).

 

But this can't be the final solution, as Apple Mail should be able to do it, too.

 

Currently I'm out of ideas... Maybe someone else can help.

 

Best regards,

Eike Hoffmann

MacBook Pro (Retina, 13-inch, Late 2013), OS X Yosemite (10.10.4), null

Posted on Jul 13, 2015 1:35 AM

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Q: 10.10.4 Mail SMTP problem

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  • by eike.hoffmann,

    eike.hoffmann eike.hoffmann Jul 27, 2015 4:10 AM in response to ClausFromSchwäbischHall
    Level 1 (0 points)
    Jul 27, 2015 4:10 AM in response to ClausFromSchwäbischHall

    Claus,

     

    no, did not work for me

     

    Viele Grüße, Eike

  • by twoguess,

    twoguess twoguess Aug 6, 2015 1:18 PM in response to ASnoeren
    Level 1 (4 points)
    Mac OS X
    Aug 6, 2015 1:18 PM in response to ASnoeren

    interesting....

  • by joedjjjjj,

    joedjjjjj joedjjjjj Aug 13, 2015 7:03 PM in response to eike.hoffmann
    Level 1 (0 points)
    Aug 13, 2015 7:03 PM in response to eike.hoffmann

    I can confirm that the final release of 10.10.5 does not fix this bug.

  • by giovi73,

    giovi73 giovi73 Aug 16, 2015 4:59 AM in response to eike.hoffmann
    Level 1 (0 points)
    Aug 16, 2015 4:59 AM in response to eike.hoffmann

    Hi, I had the same problem and I tried many many suggestions and tricks I found here and on the web.

    But none worked for me. I spent the whole night making several attempts 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



    smtp_configuration_yosemite10.10.5.png

  • by Toke Lahti,

    Toke Lahti Toke Lahti Aug 17, 2015 5:24 AM in response to eike.hoffmann
    Level 1 (123 points)
    Aug 17, 2015 5:24 AM in response to eike.hoffmann

    I also have this problem and since I noticed some inconsistence when editing Accounts.plist manually and via appleMail's settings, I dug some more and found that Mail also changes settings in /Users/<username>/Library/Containers/com.apple.mail/Data/Library/Preferences/com.apple.mail.plist .

     

    When these "container" settings are used?

    Are they corrupt if smtp server's port is listed as "string", etc. and might this affect how appleMail behaves?

    My authenticating smtp settings also has "automatically detect" checked but grayed out, so I can't uncheck it...

  • by ackiid,

    ackiid ackiid Aug 18, 2015 2:37 AM in response to giovi73
    Level 1 (0 points)
    Aug 18, 2015 2:37 AM in response to giovi73

    apparently this works because you have disabled secure authentication - AllowInsecureAuthentication > false

  • by ackiid,

    ackiid ackiid Aug 18, 2015 2:52 AM in response to eike.hoffmann
    Level 1 (0 points)
    Aug 18, 2015 2:52 AM in response to eike.hoffmann

    Just to confirm that 10.10.5 update did not fix Mail SSL issue for me

  • by ackiid,

    ackiid ackiid Aug 18, 2015 3:42 AM in response to ackiid
    Level 1 (0 points)
    Aug 18, 2015 3:42 AM in response to ackiid

    Managed to fix my issue, here is how:

     

    Go to Mail > Preferences > Accounts
    Select your account, go to SMTP > Edit server list
    Delete SMTP server account completely and restart everything
    Create the account again

  • by giovi73,

    giovi73 giovi73 Aug 19, 2015 12:41 AM in response to ackiid
    Level 1 (0 points)
    Aug 19, 2015 12:41 AM in response to ackiid

    Before making the changes that I wrote above, I tried to change only the tag "AllowInsecureAuthentication" from true to false but I couldn't send email, the problem was still there. And I tried also all the possible solutions other people wrote but the only solution that worked for me is what I wrote.


    I upgraded to Yosemite 10.10.5 and in that moment started the problem, so I suggest people not upgrade to 10.10.5.


    I know that remove and install account again works but I didn't consider this solution: I have 4 accounts IMAP and tens of thousands of messages stored in different sub directory so I preferred to find another solution.





  • by ackiid,

    ackiid ackiid Aug 19, 2015 12:56 AM in response to giovi73
    Level 1 (0 points)
    Aug 19, 2015 12:56 AM in response to giovi73

    Not the account, only SMTP server used needs to be deleted and then created again, IMAP stays intact and all messages as well :>

  • by giovi73,

    giovi73 giovi73 Aug 19, 2015 1:05 AM in response to ackiid
    Level 1 (0 points)
    Aug 19, 2015 1:05 AM in response to ackiid

    That solution didn't' work for me: I have 3 STMP server accounts, I deleted them and create them again but I couldn't send email.

    As I wrote, the only solution that worked for me is the one I posted.

     

    Thanks anyway for your feedback.

  • by Toke Lahti,

    Toke Lahti Toke Lahti Aug 19, 2015 7:46 AM in response to ackiid
    Level 1 (123 points)
    Aug 19, 2015 7:46 AM in response to ackiid

    ackiid wrote:

     

    apparently this works because you have disabled secure authentication - AllowInsecureAuthentication > false

    You mean unchecking "Allow insecure..." removes graying-out from "Automatically detect.." and then I can once again uncheck it?

    Sorry, doesn't work.

  • by Toke Lahti,

    Toke Lahti Toke Lahti Aug 19, 2015 7:59 AM in response to ackiid
    Level 1 (123 points)
    Aug 19, 2015 7:59 AM in response to ackiid

    joedjjjjj wrote:

     

    I can confirm that the final release of 10.10.5 does not fix this bug.

    Not for me either.

  • by giovi73,

    giovi73 giovi73 Aug 19, 2015 8:28 AM in response to Toke Lahti
    Level 1 (0 points)
    Aug 19, 2015 8:28 AM in response to Toke Lahti

    Uncheck it didn't work for me too. That's why I published those instruction above.

  • by giovi73,

    giovi73 giovi73 Aug 19, 2015 8:30 AM in response to Toke Lahti
    Level 1 (0 points)
    Aug 19, 2015 8:30 AM in response to Toke Lahti

    If you have "automatically detect" checked but grayed out (as I had), you have to try to modify the accounts.plist file manually but before remember to close the Mail.app.

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