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SOLVED Sending to Gmail error did not encrypt this message

Discussion in 'E-mail Discussion' started by Akylas, May 8, 2018.

  1. Akylas

    Akylas Registered

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    Hello,

    We experiencing unencrypted messages problem for all outgoing email messages from CPanel users to GMail. GMail shows received email messages from our server with red lock and notification:
    security: XXX did not encrypt this message.

    We have checked all configurations and tried to send emails from Webmail (Horde, Roundcube) and via SMTP with enabled SSL/TLS, but still no luck.

    Telnet from our CPanel server to google mail server:
    Code:
    Trying 64.233.161.27...
    Connected to gmail-smtp-in.l.google.com.
    Escape character is '^]'.
    220 mx.google.com ESMTP s206-v6si4343957lja.329 - gsmtp
    ehlo testing
    250-mx.google.com at your service, [xxx.xxx.xxx.xxx]
    250-SIZE 157286400
    250-8BITMIME
    250-ENHANCEDSTATUSCODES
    250 SMTPUTF8
    
    
    Email sending log (with server hostname changed to xxx.server.net, sender domain to domains.com, sender email to host@domain.com and receiver email to receiver@gmail.com):
    Code:
    2018-05-08 22:43:11 [10931] SMTP connection from [::1]:53448 I=[::1]:587 (TCP/IP connection count = 2)
    2018-05-08 22:43:12 [11049] H=(xxx.server.net) [::1]:53448 I=[::1]:587 Warning: Sender rate 1.0 / 1h
    2018-05-08 22:43:13 [11049] 1fG8W0-0002sD-EC H=(xxx.server.net) [::1]:53448 I=[::1]:587 Warning: Message has been scanned: no virus or other harmful content was found
    2018-05-08 22:43:13 [11049] 1fG8W0-0002sD-EC <= host@domain.com H=(xxx.server.net) [::1]:53448 I=[::1]:587 P=esmtpsa X=TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128 CV=no SNI="localhost" A=dovecot_plain:host@domain.com S=763 M8S=0 id=20180508224311.Horde.735-D8VT-B1_iOdm7WAKY6L@xxx.server.net T="One more tima testing" from <host@domain.com> for receiver@gmail.com
    2018-05-08 22:43:13 [11055] cwd=/var/spool/exim 3 args: /usr/sbin/exim -Mc 1fG8W0-0002sD-EC
    2018-05-08 22:43:13 [11055] 1fG8W0-0002sD-EC Sender identification U=domainc D=domain.com S=host@domain.com
    2018-05-08 22:43:13 [11055] 1fG8W0-0002sD-EC SMTP connection outbound 1525808593 1fG8W0-0002sD-EC domain.com receiver@gmail.com
    2018-05-08 22:43:14 [11049] SMTP connection from (xxx.server.net) [::1]:53448 I=[::1]:587 closed by QUIT
    2018-05-08 22:43:14 [11055] 1fG8W0-0002sD-EC => receiver@gmail.com F=<host@domain.com> P=<host@domain.com> R=dkim_lookuphost T=dkim_remote_smtp S=2081 H=gmail-smtp-in.l.google.com [64.233.161.26]:25 I=[xxx.xxx.xxx.xxx]:37210 C="250 2.0.0 OK 1525808595 t66-v6si12294885lje.83 - gsmtp" QT=2s DT=1s
    2018-05-08 22:43:14 [11055] 1fG8W0-0002sD-EC Completed QT=2s
    
    
    Please help us with this issue.

    Thank you!
     
    #1 Akylas, May 8, 2018
    Last edited by a moderator: May 8, 2018
  2. cPanelMichael

    cPanelMichael Technical Support Community Manager
    Staff Member

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    Hello @Akylas,

    It looks like the STARTSSL command is missing. Here's how the same command looks from a test system:

    Code:
    # telnet gmail-smtp-in.l.google.com 25
    Trying 64.233.180.27...
    Connected to gmail-smtp-in.l.google.com.
    Escape character is '^]'.
    220 mx.google.com ESMTP a10-v6si1874069oic.405 - gsmtp
    ehlo testing
    250-mx.google.com at your service, [208.74.121.106]
    250-SIZE 157286400
    250-8BITMIME
    250-STARTTLS
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    I've seen this issue arise in the past when a hosting provider/data center utilized Cisco hardware with SMTP/packet inspection enabled. Can you check with your hosting provider or data center to see if they have implemented any form of SMTP/packet inspection?

    Thank you.
     
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  3. Akylas

    Akylas Registered

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    Thank you for your fast reply.

    Yes this was the case of this problem. And they refused to disable this option. It's time to move to other datacenter...

    Thank you!
     
  4. cPanelMichael

    cPanelMichael Technical Support Community Manager
    Staff Member

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    Twitter:
    Hello @Akylas,

    While it's unfortunate your data center was unwilling to help, I'm glad to see you were able to confirm the cause of the issue.

    Thank you for updating us with the outcome.
     
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  5. Raviraj saini

    Raviraj saini Registered

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    I am getting the similar problem but not able to fix that.. please let me know how I can fix that.. I have 4 other servers but didn't have this issue on another server.
     
  6. cPanelMichael

    cPanelMichael Technical Support Community Manager
    Staff Member

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    Twitter:
    Hello @Raviraj saini,

    Can you let us know the results when running the below command from your cPanel & WHM server's command line?

    Code:
    telnet gmail-smtp-in.l.google.com 25
    Thank you.
     
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