evan_tech -- using ssmtp with gmail

06:32 pm, 12 Feb 06

using ssmtp with gmail

I typically don't configure a mail setup on my workstations, but some programs, like darcs, like to be able to send email. Here's how to offload mail sending to gmail with ssmtp, which is a tiny mail MTA.

apt-get install ssmtp

In /etc/ssmtp/ssmtp.conf:

mailhub=smtp.gmail.com:587
UseTLS=Yes
UseSTARTTLS=Yes
AuthUser=gmail login
AuthPass=gmail password
hostname=your hostname
FromLineOverride=YES

In /etc/ssmtp/revaliases:

localusername:realemailaddress:smtp.gmail.com:587

Test with "echo hello | mail my@email.address".

(The gotcha is apparently the port number: some sources give a different port and that just makes ssmtp block(?).)

dan_erat	Grr, why doesn't ssmtp support per-user config files? I don't like putting my passwords into world-readable files, even though this is a (usually) single-user system. :/ I'm currently using the similar-seeming esmtp to send through Comcast; I wasn't able to get it to talk TLS to Gmail the last time I tried. You have inspired me to give it another shot.
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evan	Hmm... now that I look at it, you'd think sendmail (which is I believe the executable programs like "mail" invoke to deliver mail) could look at the owner and read a conf file from there. You can probably just symlink /etc/whatever to ~/.gmail-password :P
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dan_erat I'm about to give up and go to bed. STARTTLS is such a black box to me... I can see that esmtp starts to do the TLS negotiation with the server, and then it sees something that it doesn't like between the server's cert and the Thawte one that I have locally and spits out a meaningless message.

Re the port confusion that you mentioned: If you're talking about port 465, that one is using SSL — try openssl s_client -connect smtp.gmail.com:465 -showcerts, for instance. Maybe ssmtp doesn't know how to talk to it?

(To bring the two preceding paragraphs together, I think that I'm going to ditch TLS and try using stunnel to connect to 465 instead.)

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dan_erat

Success!

In a script that gets run when I log in:

/usr/sbin/stunnel -c -D 4 -d 8111 -r smtp.gmail.com:465

In ~/.esmtprc:

hostname localhost:8111
username = "my_address@gmail.com"
password = "my_password"
mda = "/usr/bin/procmail -d my_local_username"

In ~/.muttrc:

set sendmail="/usr/bin/esmtp"

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evan Does esmtp not speak ssl itself? That stunnel's a bit weird.

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evan	Oh, now I see this in context of your other comment. If you search for [gmail smtp linux] or something like that there's a lengthy guide that uses postfix or one of the bigger setups. But it also goes through setting up the certs, so maybe that'll help.
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dan_erat	I looked through that guide yesterday but still couldn't get STARTTLS working. It wasn't clear to me whether I was doing something wrong or there was a bug in libesmtp.
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Anonymous

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- Anonymous
  
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  - dan_erat Thanks! I'll give this a try if the stunnel/esmtp setup breaks at some point. :)
    
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mart
I fear the day that ISPs stop providing SMTP relays because “everyone” uses webmail.

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evan	Does esmtp not speak ssl itself? That stunnel's a bit weird.
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dan_erat	Thanks! I'll give this a try if the stunnel/esmtp setup breaks at some point. :)
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mart	I fear the day that ISPs stop providing SMTP relays because “everyone” uses webmail.
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