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Emails from gmail bouncing back from exchange

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  • 08-03-2013 11:18am
    #1
    RonyPonyBah
    Registered Users Posts: 309 ✭✭


    Hi !

    Have an exchange server and when someone emails from a gmail account it bounces back to the sender about 2 hours later.

    All other emails are sending/receiving fine

    Here is a an example
    From: Mail Delivery Subsystem <mailer-daemon@googlemail.com>
Date: 8 March 2013 10:05:16 GMT
To: ----------@gmail.com
Subject: Delivery Status Notification (Delay)
This is an automatically generated Delivery Status Notification

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipient has been delayed:

    Administrator@------------.ie

Message will be retried for 2 more day(s)

Technical details of temporary failure: 
Unspecified Error (SENT_SECOND_EHLO): Unknown error -1

----- Original message -----

DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
       d=gmail.com; s=20120113;
       h=mime-version:x-received:date:message-id:subject:from:to
        :content-type;
       bh=CqtIMquVqps2gQgNmr3ICzh8LHTFJorOAJkvfbd/+u4=;
       b=nkLYwIlRwL38K4pcicIIIlVliu/+Qgd2TEcpxZEDIPdpfIlRxReETS9cXnhSw3agWd
        vk8/5ZMIAavIBnmA28n6COMkr1aPI6vFwHngNyaMZouLkRTj6SVyT7LyBooYto3qdsOt
        OF+cznsmULOPkmM4BLtK/E4CkHkg7nfTmCQjlG9+qYBtw5Fu6Wpgy0NTdFjTaTt8rsEe
        JlKM42s1aUpjrTTG/zFKpj/Uba65Ey0uQfzeg03rrt5Mh57h9CGKPYd499yTpw2mK7jp
        hKec5gduNManr7kGBc/DqAiMomuaIG9nFV3qAffz4SpoZmvC+0VovjurcY0RdRbeSW/W
        ITGQ==
MIME-Version: 1.0
X-Received: by 10.194.63.109 with SMTP id f13mr52745215wjs.11.1362646523469;
Thu, 07 Mar 2013 00:55:23 -0800 (PST)
Received: by 10.216.232.132 with HTTP; Thu, 7 Mar 2013 00:55:23 -0800 (PST)
Date: Thu, 7 Mar 2013 08:55:23 +0000
Message-ID: <CAM-LL7xwSrRhsmvR6MNqXqn=k8y6Ue_bDnMqGXL8oS=0NEa+7A@mail.gmail.com>
Subject: 
From: *********** <-------------@gmail.com>
To: Administrator <Administrator@-------------.ie>
Content-Type: multipart/alternative; boundary=047d7b86db60fc659204d751dd10

    Thanks !


Comments

  • Options
    #2
    ressem
    Registered Users Posts: 2,426 ✭✭✭ressem


    I haven't seen this problem myself but a google of SENT_SECOND_EHLO + exchange suggests that a common cause is Exchange trying to negotiate a TLS secured channel with the Gmail sender and failing.

    What version of exchange do you use?
    Is this a new setup or is it an old setup that used to work with gmail?
    Does your exchange installation use a self-signed certificate or a purchased one for encrypting the Secure channel?
    Any chance that the certificate originally bought / created and installed has expired?


  • Options
    #3
    Merl1n
    Registered Users Posts: 251 ✭✭Merl1n


    are you sending mail direct using dns or are you relaying through an isp
    if your not using an isp you could try relay through your provider and see if it works


  • Options
    #4
    BailMeOut
    Registered Users Posts: 2,985 ✭✭✭BailMeOut


    I would check the TLS certificate on your SMTP server. It might be expired. GMAIL will always try send using TLS and if your cert is expired then you would get an error like this. Also check its time/date/time zone on your SMTP server are set correctly.

    Also what type of firewall do you have in front of your SMTP server? If a Cisco ASA you need to be careful using ESMTP/SMTP Inspection as it will break TLS email. If you have a Cisco ASA and have SMTP inspect enabled then disable it.


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