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intermittent tls failure with smtp.gmail.com

#1256

sometimes ssl/tls negotiation is failing on some of my google-apps accounts... there's a socket connection, but then it times out. the same account works fine other times, and other google-apps accounts also work fine. below are logs first from a failing attempt, and then from a successful attempt with a different account :

<<>>

09:14:53 Sending request (10)
09:14:53 Handling request
09:14:53 Ready to run action
09:14:53 Clearing connection to smtp.gmail.com
09:14:53 Trying to connect to smtp.gmail.com on port 465
09:14:53 Successful connection on socket 52.
09:15:03 Error: Time limit (10s) reached while trying to read data (smtp.gmail.com)
09:15:03 Initiating secure connection...
09:15:03 Error: Failed SSL handshake (0/5).
09:15:03 Error code: 9
09:15:03 Failed action (0). Reset observed read/write timeouts: 8/8

<<>>

09:25:36 Sending request (49)
09:25:36 Handling request
09:25:36 Ready to run action
09:25:36 Clearing connection to smtp.googlemail.com
09:25:36 Trying to connect to smtp.googlemail.com on port 587
09:25:36 Successful connection on socket 59.
09:25:36 S: 220 smtp.googlemail.com ESMTP en5sm2989885wib.18 - gsmtp
09:25:36 C: EHLO [192.168.2.1]
09:25:36 S: 250-smtp.googlemail.com at your service, [90.214.102.109]
09:25:36 S: 250-SIZE 35882577
09:25:36 S: 250-8BITMIME
09:25:36 S: 250-STARTTLS
09:25:36 S: 250-ENHANCEDSTATUSCODES
09:25:36 S: 250-PIPELINING
09:25:36 S: 250-CHUNKING
09:25:36 S: 250 SMTPUTF8
09:25:36 C: STARTTLS
09:25:37 S: 220 2.0.0 Ready to start TLS
09:25:37 Initiating secure connection...
09:25:37 Setup of secure connection complete (TLSv1).
09:25:37 Cipher: RC4-SHA SSLv3 Kx=RSA Au=RSA Enc=RC4(128) Mac=SHA1
09:25:37 C: EHLO [192.168.2.1]
09:25:37 S: 250-smtp.googlemail.com at your service, [90.214.102.109]
09:25:37 S: 250-SIZE 35882577
09:25:37 S: 250-8BITMIME
09:25:37 S: 250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN XOAUTH
09:25:37 S: 250-ENHANCEDSTATUSCODES
09:25:37 S: 250-PIPELINING
09:25:37 S: 250-CHUNKING
09:25:37 S: 250 SMTPUTF8
09:25:37 Retrieving password (keychain or user request)
09:25:37 C: AUTH PLAIN ••••••••••
09:25:37 S: 235 2.7.0 Accepted
09:25:37 C: MAIL FROM:craig@trampolinesystems.com SIZE=287
09:25:38 S: 250 2.1.0 OK en5sm2989885wib.18 - gsmtp
09:25:38 C: RCPT TO:craig@mccraig.net
09:25:38 S: 250 2.1.5 OK en5sm2989885wib.18 - gsmtp
09:25:38 C: DATA
09:25:38 S: 354 Go ahead en5sm2989885wib.18 - gsmtp
09:25:38 C: From: "craig mcmillan" craig@trampolinesystems.com
09:25:38 C: To: "craig mcmillan" <290 bytes>
09:25:38 C: ... @trampolinesystems.com>
09:25:38 C: MIME-Version: 1.0
09:25:38 C: X-Mailer: MailMate (1.9.2r5107)
09:25:38 C:
09:25:38 C: blah
09:25:38 C: .
09:25:39 S: 250 2.0.0 OK 1441358739 en5sm2989885wib.18 - gsmtp
09:25:39 Completed action (0). Observed read/write timeouts: 8/8

Reported by craig mcmillan · September 4th, 2015 @ 09:33 AM

State: new
Milestone: none
Assigned to: benny benny

Activity

  1. benny
    benny

    Try the latest test version: Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane.

    If that does not help then let me know and switch to port 587. That should work.

    September 4th, 2015 @ 11:10 AM

  2. craig mcmillan
    craig mcmillan

    i've not seen the problem since i upgraded

    that's not absolute confirmation that it's gone away - it was only intermittent - but i remain ever hopeful

    thanks

    September 7th, 2015 @ 09:31 AM

  3. benny
    benny
    • State changed from new to resolved

    Ok, I'll mark it as resolved for now, but you can still add comments.

    September 7th, 2015 @ 10:02 AM

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