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How do I tweak sendmail.cf directly (without going through m4 or .mc files) to make gmail (with SMTP AUTH) my smart relay? Notes:

  • With Comcast, I just put "DSsmtp.comcast.net" in sendmail.cf, since they authenticate by IP, and don't require "SMTP AUTH"

  • I'm now w/ Qwest, and want to use gmail's SMTP AUTH server. I realize I could use smtp.q.com, but prefer gmail's.

  • I've confirmed I can send email using gmail's server:


    > openssl s_client -connect smtp.gmail.com:465
    CONNECTED(00000003)

    [... lots of certificate stuff ...]

    220 mx.google.com ESMTP y7sm198769pbg.43 
    ehlo 
    250-mx.google.com at your service, [xxx.xxx.xxx.xxx] 
    250-SIZE 35882577 
    250-8BITMIME 
    250-AUTH LOGIN PLAIN XOAUTH 
    250 ENHANCEDSTATUSCODES 
    auth plain AGNhcnRlci5iYXJyeQxxxxxxxxxx 
    235 2.7.0 Accepted 
    mail from:  
    250 2.1.0 OK y7sm198769pbg.43 
    rcpt to:  
    250 2.1.5 OK y7sm198769pbg.43 
    data 
    354  Go ahead y7sm198769pbg.43 
    Subject: Hi there 

    End of message 

    QUIT 
    DONE 
  • Based on the above, the sendmail changes I need are:

    • connect on port 465, not port 25 (although port 25 w/ STARTTLS also works)

    • connect using SSL

    • Send "auth plain AGNhcnRlci5iYXJyeQxxxxxxxxxx" after ehlo and before rcpt.

  • I know that tweaking the mc file and running m4 is the correct way to do this, but my .cf file is hand-customized and quite fragile, so I'm hoping to avoid that.

  • I realize I could have sendmail deliver to localhost:26 and have a Perl script running there that relays to smtp.gmail.com:465 using openssl (and passes data as is, except for the "AUTH PLAIN" line), but this seems ugly.

Other solutions appreciated. EG, if anyone knows of a free open relay...

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Why do you want to directly edit the .cf ? Have you lost the .mc and cannot recreate it? –  adamo May 1 '11 at 18:45
    
That's correct. I've edited sendmail.cf by hand quite a lot, so the mc file I have is not even close to the cf file. –  barrycarter May 2 '11 at 4:03
    
If you've documented your edits, it is possible that one can produce a working .mc that does what you want. –  adamo May 2 '11 at 5:15
    
I haven't (this sendmail.cf file started in 1997), but that is an idea... try to recreate my sendmail.cf by tweaking foo.mc until the resulting foo.cf matches. I may try this or just find a non-free-but-cheap POP-before-SMTP server I can use. –  barrycarter May 2 '11 at 16:35
    
Hm... poprelay.sourceforge.net –  adamo May 2 '11 at 17:35
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1 Answer 1

Is it imperative to use Google's smtp as a relay? If not, maybe this article can help.

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