#392 new
Christian Fletcher

Unable to send with Gmail

Reported by Christian Fletcher | May 8th, 2013 @ 10:29 PM

Unable to send messages through gmail SMTP. I'm getting a fail message almost 30 seconds after attempting to send. Retry and edit, then re-send do not work, but Gmail is saving a draft of my message which I can send through web-based gmail. All other gmail functions seem normal.

This appears similar to error described in ticket #5.

Screen grab of error message:

https://dl.dropbox.com/s/vz5gymbfeeizxg6/Screen%20Shot%202013-05-08...

Comments and changes to this ticket

  • Eric A. Meyer

    Eric A. Meyer May 9th, 2013 @ 01:22 AM

    I’ve been having exactly the same problem today, as has Alexandre Takacs on the MailMate Users list. The message is the same, except for the “t41….11” string near the end. It started for me some time around 3pm EDT/1900 UTC. Benny’s diagnosis is problems on GMail’s end; I’ll mail him a complete log of one of my attempts to see if anything more precise can be determined, but we may just have to wait it out.

  • Eric A. Meyer

    Eric A. Meyer May 9th, 2013 @ 01:30 AM

    One more thing I neglected to mention: I’ve noticed that the password used to send mail is not stored by MailMate, probably because the login fails so MailMate assumes the password is no good. So I have to re-enter it each time I try (and fail) to send mail through smtp.gmail.com.

    Note: I don’t store my passwords in my keychain on the premise that should my laptop be stolen, the thief won’t be able to get new mail or receive old mail without also having my email password. Thus I have to enter it when launching MailMate, and on my first mail send. So the behavior I describe here is pretty much by design and doesn’t shed any light on the situation, but I figured I’d mention it just in case.

  • benny

    benny May 9th, 2013 @ 06:34 AM

    Ok, we have 3 users with this problem. So far, only reports for MailMate. I don't know if any of you have tried with other email clients (not web interface).

    I don't have problems myself. If I connect manually I get:

    telnet smtp.gmail.com 25
    Trying 173.194.69.109...
    Connected to gmail-smtp-msa.l.google.com (173.194.69.109).
    

    You could try replacing smtp.gmail.com with 173.194.69.109 to try the same server as I do. This is to see if the problem is related to which SMTP server MailMate connects to. This is not a permanent solution if it works.

    What do you get as reply if you enter:

    telnet smtp.gmail.com 25
    

    @Christian: The issue has also been briefly discussed on the mailing list, but I'll use this ticket to track the issue. Basically, the error says the problem is Google, but since only MailMate users seem to be affected then I'm going to assume that it is somehow MailMate related.

    @Eric: I'll have to look into the repeated password requester later. Maybe you can remind me :-) The log file you sent looks fine to me. Google just rejects with a temporary problem. It happens after the message is uploaded which makes it possible that the problem is somehow triggered by something in the message (in which case the error message is misleading).

  • benny

    benny May 9th, 2013 @ 06:59 AM

    The following is a general workaround for SMTP issues. Launch the postfix daemon on your own machine:

    sudo postfix start
    

    Then edit the Gmail account settings such that:

    SMTP Server: localhost User Name:

    That is, no user name.

    After that you should be able to send messages using an SMTP server on your own machine :-)

    (Tested on 10.8, but I believe it also works on 10.6/10.7)

    Note that the name of your local machine is added to the Received headers of such messages. Most likely configurable or you can change the name of your machine if this is important to you.

  • Alexandre Takacs

    Alexandre Takacs May 9th, 2013 @ 08:13 AM

    I am also seeing this problem with google apps accounts (google hosted mail, most probably using the same infrastructure as gmail).

    It is most likely not content related (I have various messages with various type of content and destinations not going through).

    As of postfix it did not want to work "out of the box" on my Mac (10.8) - had to manually create so directories. It is now up & running but still get

    “error:0200203D:system library:connect:Connection refused” “error:2007306E:BIO routines:CONN_STATE:nbio connect error”

    so I guess it is a little more involved than just starting it...

  • benny

    benny May 9th, 2013 @ 08:38 AM

    @Alexandre: My 10.8 install is relatively new, but I do install a lot of developer related stuff which might explain it. Sorry about the inconvenience.

    Could you try the telnet command I wrote further above:

    telnet smtp.gmail.com 25
    

    An IP for the server might help me reproduce the issue (I'm still in the guessing phase).

    Could you also try an older version of MailMate such as the latest public release.

  • benny

    benny May 9th, 2013 @ 08:44 AM

    Could you also try setting an explicit port, in particular, 25. The log file I got from Eric uses port 465. (I just tried sending using port 465 without problems, but maybe there is more than 1 trigger for this problem.)

  • benny

    benny May 9th, 2013 @ 08:47 AM

    Maybe related: http://productforums.google.com/forum/#!topic/gmail/txNEW_06QVc

    Do any of you use email aliases? Does it make a difference if you send from the Gmail login-address? (Still guessing.)

  • Alexandre Takacs

    Alexandre Takacs May 9th, 2013 @ 09:51 AM

    @Benny - I can connect to port 25 (which is a surprise, I thought google insisted to use 465):

    MBP13:~ alex$ telnet smtp.gmail.com 25
    Trying 173.194.70.109...
    Connected to gmail-smtp-msa.l.google.com.
    Escape character is '^]'.
    220 mx.google.com ESMTP c44sm3092256eeb.4 - gsmtp
    helo atc.ch
    250 mx.google.com at your service
    MAIL FROM: a.takacs@activ.biz
    530 5.7.0 Must issue a STARTTLS command first. c44sm3092256eeb.4 - gsmtp
    

    don't know what how to do a TLS handshake through telnet, though...

  • benny

    benny May 9th, 2013 @ 10:32 AM

    @Alexandre: I tried sending with gmail-smtp-msa.l.google.com. Still no problem.

    To connect with STARTTLS you need something more powerful than telnet. This should work:

    openssl s_client -starttls smtp -crlf -connect smtp.gmail.com:25
    

    The same for port 587. For port 465 it is more simple:

    openssl s_client -crlf -connect smtp.gmail.com:465
    
  • Alexandre Takacs

    Alexandre Takacs May 9th, 2013 @ 01:12 PM

    Ok I can now definitely report that the issue is somehow related to the interaction between MM and google servers.

    I went into the trouble of setting up apple Mail.app with the same settings and the mail are going out just fine.

    I have changed the SMTP parameters to use another non-Google server from MM (one I can trick into relaying my mails) and the mails are also going out as expected (which is my short term solution to this rather annoying issue).

    I will try latter to fire up WireShark and record traffic with Google and non Google servers but I'm not convinced it will be useful as I suppose that all the "talking" is done within a secure session ?

  • Christian Fletcher

    Christian Fletcher May 9th, 2013 @ 01:26 PM

    @benny I do use aliases, but sending from the address connected to the account does not work. Still get the error.

    Using 173.194.69.109 instead of SMTP.gmail.com does not work.

    Port 25 in place of port 465 does not work.

  • benny

    benny May 9th, 2013 @ 01:27 PM

    @Alexandre: Just to have more example data, could you provide a log from the Activity Viewer of an attempt to send a message? And maybe also provide this file:

    ~/Library/Application Support/MailMate/Sources.plist
    

    Send it in a private email.

    Did you try an older version of MailMate as asked further above. Just so that I know whether to look into recent changes or look into changed Gmail behaviour?

  • benny

    benny May 9th, 2013 @ 01:34 PM

    @Christian: Thanks. This is a frustrating problem. Could you send me a log as well (open Activity Viewer ⌥⌘0 and locate the SMTP connection, then attempt to send a message)?

    Since it works for me (and probably others as well) then there must be something in your setup which triggers this problem. Are you using Google Apps or plain (free) Gmail? I think the others are on Google Apps.

  • benny

    benny May 9th, 2013 @ 01:35 PM

    @Eric and @Alexandre: Remember to enable watching for changes to this ticket. As far as I can see only Christian and I are notified when the ticket is updated.

  • Christian Fletcher

    Christian Fletcher May 9th, 2013 @ 02:16 PM

    @benny activity viewer log sent. I am using Google Apps.

  • macmath

    macmath May 9th, 2013 @ 04:28 PM

    I upgrade devoutly every morning, so I've been using 3384 from the first day it became available. However, it was only this morning that I began to have this difficulty. It is intermittent. Someone to whom I could not reply earlier this morning I was able to reply to just now. However, now I am unable to reply to someone else. The behavior has seemed to change now.

    This problem only occurs with the google apps account that my university has. My private gmail account works fine.

    Just now I see that it is working fine for me again. It went through a phase of not showing me an error message but saying (in the "State" column) "Pending Submission". I closed the Activity Viewer and deleted those "Pending Submission' to see if that was a side-effect of having the Activity Viewer open. However, now everything is sending just fine.

  • macmath

    macmath May 9th, 2013 @ 05:15 PM

    The problem has returned and does not (seem to) occur when using Opera Mail (built in to the Opera Web browser. I just sent two messages (essentially) simultaneously to Benny. The non-MailMate browser sent the email.
    Does anyone remember how/where to get older versions of MailMate?

  • macmath

    macmath May 9th, 2013 @ 05:28 PM

    I discovered that the reason I was shown "Pending submission" instead of the Error message is that there was a composition window hidden behind the view window which had the Error message visible on it. Once I answered the Error message, then all the messages which were "Pending submission" came forward one at a time with the Error message. Sorry! Everyone.

    The issue still occurs with version 3323 of MailMate, and only through my Google Apps (work) account.

  • benny

    benny May 9th, 2013 @ 05:59 PM

    Current status:

    • The problem started due to a Google change. It does not help to use an older version of MailMate.
    • It seems to only affect Google Apps users.
    • I was not able to reproduce the issue with Google Apps (I registered for a trial month).

    I've been offered a test account on a Google Apps account affected by this problem. Hopefully I can then reproduce the problem and find out more.

  • benny
  • benny

    benny May 9th, 2013 @ 06:29 PM

    I can reproduce it now. Hopefully that leads to something.

  • benny

    benny May 9th, 2013 @ 07:15 PM

    • State changed from “new” to “reproduced”

    It seems I can fix the issue by taking the Drafts mailbox offline before writing a new message and sending it. The effect of this is that Google does not see the message before it is sent. In other words, Google does not already know a message with the same Message-ID (which might somehow trigger a bug in their server).

    @anyone: Please try this and confirm/reject this theory.

  • phillipw

    phillipw May 9th, 2013 @ 07:24 PM

    @benny Yes, I can confirm that your suggested workaround seems to fix the issue. I've tested it with various Google for Domains/Google Apps accounts that I use and all seem to now successfully send email.

  • Christian Fletcher

    Christian Fletcher May 9th, 2013 @ 07:28 PM

    @benny That workaround does not work for me.

  • benny

    benny May 9th, 2013 @ 07:29 PM

    • State changed from “reproduced” to “closed”

    @phillipw: Great, at least there exists a workaround now.

    I suggest to everyone experiencing this issue that they contact Google. This is not a MailMate bug. To emphasize this I'll close this ticket, but it would be great if one of you updated this ticket if Google fixes the problem. I'll consider possible workarounds since they probably won't.

  • benny

    benny May 9th, 2013 @ 07:31 PM

    • State changed from “closed” to “cantreproduce”

    @Fletcher: Argh :-) Can you retry just to make sure. Also try taking the Gmail account offline (you can still send messages).

  • Christian Fletcher

    Christian Fletcher May 9th, 2013 @ 07:42 PM

    @benny Sorry! :)

    Retried:

    Taking DRAFTS offline does not work.

    Taking the Google Apps account offline does work. (Although this is, obviously, not a great long-term fix.)

  • Alexandre Takacs

    Alexandre Takacs May 9th, 2013 @ 07:46 PM

    I can confirm that I have the same findings as Christian.

  • benny

    benny May 9th, 2013 @ 08:00 PM

    • State changed from “cantreproduce” to “closed”

    @Christian: Glad to hear it works.

    @Alexandre: I assume you mean the final findings of Christian.

    I'll re-close the ticket.

  • Alexandre Takacs

    Alexandre Takacs May 9th, 2013 @ 08:02 PM

    Yes - it works if I put the account offline.

  • benny

    benny May 9th, 2013 @ 08:04 PM

    @Alexandre: Just to emphasize. It is sufficient to take “[Gmail]/Drafts” offline.

  • Alexandre Takacs

    Alexandre Takacs May 9th, 2013 @ 08:09 PM

    I'm afraid not - Only works if I put the whole account offline - just tested now

  • benny

    benny May 9th, 2013 @ 10:05 PM

    @Alexandre: Could you check which folder MailMate uses for saving drafts (Mailbox ▸ Mailbox Type). Maybe you need to take a different mailbox than “[Gmail]/Drafts” offline.

  • benny

    benny May 10th, 2013 @ 06:02 AM

    @Alexandre: And even if this mailbox says “Drafts (Offline)” then you still get the message with a “Temporary System Problem”? That kind of sends my theory down the drain.

  • benny

    benny May 10th, 2013 @ 06:04 AM

    @Alexandre: Note that it must be a new message. You cannot take the Drafts mailbox offline and then try to send a message which previously failed (although in that case taking the account offline would not help either).

  • benny

    benny May 10th, 2013 @ 06:56 PM

    • State changed from “closed” to “resolved”

    It works for me too. I guess Google fixed it — until next time.

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