TIP: Gmail and sSMTP

[ellotheth]

TIP: Gmail and sSMTP

I recently set up Mutt with several non-Gmail accounts. When my non-Gmail SMTP server became a shade unreliable, I decided to use my Gmail SMTP server instead. (That's right, my Gmail server with non-Gmail email addresses.) Thus began several hours worth of forum-combing, Google-combing, documentation-combing, code-combing, and solution-by-trial-and-error. After much toil, I emerged triumphant, and I thought I'd use my newfound knowledge to spare similar hapless souls.

Gmail miscellany

• Read Gmail's POP3 instructions for "other" mail clients.
• Gmail's default behavior is to overwrite any unrecognized header information with its own. So if you're composing an email as <thetove@jabberwocky.com> in Mutt/Thunderbird/what-have-you and you send it via your <slithy.tove@gmail.com> account, it will arrive as an email from <slithy.tove@gmail.com>, with the <thetove@jabberwocky.com> nowhere in sight. Hardly ideal. You need to add "Custom From Addresses" in your Gmail account settings to preserve header info from non-Gmail addresses. Go to the "Accounts" section of "Settings." Add every account with which you plan to use the Gmail SMTP server, and don't forget to specify the reply-to.

sSMTP

Here's the part that sent me spinning across the internet. Gmail and sSMTP don't play nice without a little coaxing, and clear documentation is sparse.

• Basic configuration documention/information is located in the default /etc/ssmtp/ssmtp.conf, so read it. Really. This is just a tip, not a HowTo. Jeez. Also read the contents of /usr/share/doc/ssmtp*/.
• sSMTP needs port 587. It won't work (or rather, it doesn't for me) with 465, even if Google says it should. Hence:

  Code: Select all

  mailhub=smtp.gmail.com:587

• It's just STARTTLS. Not STARTTLS and SSL, nor STARTTLS and TLS. Just STARTTLS:

  Code: Select all

  UseSTARTTLS=YES

• Login info can be put on the command line; I prefer to stuff it in here:

  Code: Select all

  AuthUser=slithy.tove@gmail.com
  AuthPass=twasbrillig

  Authentication method (AuthMethod) defaults to LOGIN, which is what we want.
• sSMTP needs to be told to pay attention to header info, too:

  Code: Select all

  FromLineOverride=YES

Caveat: With the above settings, your header info will still contain some references to Gmail: in particular, Return-Path and Sender will point to your gmail address by default. It doesn't bother me, so I haven't researched whether that's configurable.

That's it, you're golden. Happy...uh, non-Gmail Gmailing.

If this tip has been useful to you, let me know, yo. If it's completely unintelligible and worthless, let me know that too. I haven't written documentation in a long time, and I may well be out of practice.

[Sheepdogj15]

Code: Select all

AuthUser=slithy.tove@gmail.com
AuthPass=twasbrillig

i'm going to assume this isn't your real password.

hmm, interesting. right now i'm looking for a way to set up my Gentoo router/firewall box to send me alerts should someone attempt to hack it. this will definitely help (if you haven't noticed despite the "Guru" in my postbit i'm a bit of a newb at heart... i didn't even know Linux can send mail to me until today )

[ellotheth]

i'm going to assume this isn't your real password.

O botheration! No one was supposed to guess!

i didn't even know Linux can send mail to me until today

Don't worry, I'm in roughly the same boat. "What are all these weird dead.letters in $HOME? Cron is trying to email me?! Cool!"

[oliver]

I think cron only does that if your scripts generate output - send all to /dev/null (or an appropriate log file) and they'll stop

[ellotheth]

I think cron only does that if your scripts generate output - send all to /dev/null (or an appropriate log file) and they'll stop

Thanks, I did find that. It was really confusing for a while, though.

[jimonade]

i've tried various combos including the above as well as from (http://forums.gentoo.org/viewtopic-p-3011748.html) and i get the following or nothing...

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mail -s "testing ssmtp" jim@example.com

...

send-mail: Cannot open gmail.smtp.com:587
Can't send mail: sendmail process failed with error code 1

any suggestions? or, could someone post their working (gmail) ssmtp.conf?

[ellotheth]

Code: Select all

send-mail: Cannot open gmail.smtp.com:587

Should be smtp.gmail.com, I believe. Here's my ssmtp.conf:

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root=myroot@mymail.com

mailhub=smtp.gmail.com:587

rewriteDomain=

FromLineOverride=YES

UseSTARTTLS=YES
AuthUser=myemail@gmail.com
AuthPass=foobar

[jimonade]

thanks so much for the reply. ssmtp is now working.

i think my problem was the revaliases file-- i had gmail.smpt.com isntead of smtp.gmail.com.

the below ssmtp.conf works even if all revaliases are comment out. then again, its just me and root on this box.

ssmtp.conf

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root=jimonade@gmail.com
mailhub=smtp.gmail.com:587
rewriteDomain=
hostname=jimonade@gmail.com
FromLineOverride=YES
UseSTARTTLS=YES
AuthUser=jimonade
AuthPass=samplepasswd

revaliases

Code: Select all

root:jimonade@gmail.com:smtp.gmail.com:587
jim:jimonade@gmail.com:smtp.gmail.com:587

thank you ellotheth and thank you google.

[Ravak]

By default:

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-rw-r--r-- 1 root root 1285 lut  3 16:08 ssmtp.conf

So if you have any additional users/accounts I'd be careful with it.

Now by:

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-rw-r----- 1 root root 1285 lut  3 16:08 ssmtp.conf

Only root and his group can view the config. Unfrotunatenly, also only root can send mail.

So my question is how to secure config file without restricting access to mail service. I'd like to make one or two accounts for family members yet I dont want them to know my passes.

Thanks.

[jimonade]

have my ssmtp.conf at chmod 640, so im in the same boat... only root can send with ssmtp.

i only really wanted ssmtp setup so that i could have cron jobs email me stuff periodically so it suits my needs. but i can see how you'd want to enable this for users as well as root while not allowing users to see the plain text passwords.

if anyone knows how to save the ssmtp password in a chmod 640 file and reference it in ssmtp.conf allowing all system users to email with ssmtp, please share!

edit: chmod 640 so that root's group has read access

[troworld]

I'm getting:

Code: Select all

mail -v -s "testing ssmtp" myemail
asdlfjhasdfasd
fasdfasdf
Cc:
[<-] 220 mx.gmail.com ESMTP e11sm2652278qbc
[->] EHLO email@gmail.com
[<-] 250 ENHANCEDSTATUSCODES
[->] STARTTLS
[<-] 220 2.0.0 Ready to start TLS
[->] EHLO email@gmail.com
[<-] 250 ENHANCEDSTATUSCODES
Can't send mail: sendmail process failed

I have mailx and "emerge -av ssmtp" says:

Code: Select all

[ebuild   R   ] mail-mta/ssmtp-2.61  USE="ipv6 mailwrapper md5sum ssl"

[destr0yr]

I have mailx and "emerge -av ssmtp" says:

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[ebuild   R   ] mail-mta/ssmtp-2.61  USE="ipv6 mailwrapper md5sum ssl"

This works for me:

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[ebuild   R   ] mail-mta/ssmtp-2.61  USE="ipv6 -mailwrapper -md5sum ssl"

Do you absolutely require mailwrapper and md5sum? Try it without for testing purposes...

[HotBBQ]

I having problems with secure connection. Here is the error I am receiving:

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adam@Beast ~ $ mail -v -s "ssmtp test" adbowers@gmail.com
Hope this works.
Cc:
[<-] 220 mx.gmail.com ESMTP i35sm736090wxd
[->] HELO Beast
[<-] 250 mx.gmail.com at your service
[->] MAIL FROM:<adbowers@gmail.com>
[<-] 530 5.7.0 Must issue a STARTTLS command first i35sm736090wxd
send-mail: 530 5.7.0 Must issue a STARTTLS command first i35sm736090wxd
Can't send mail: sendmail process failed with error code 1

My ssmtp.conf:

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root=adbowers@gmail.com
mailhub=smtp.gmail.com:587
rewriteDomain=
hostname=adbowers@gmail.com
FromLineOverride=YES
UseSTARTTLS=YES
AuthUser=adbowers
AuthPass=***

Edit
Removing md5sum and mailwrapper from my use flags and recompiling seems to have fixed the problem. I cannot, however, mail with a user other than root.

[Elorian]

Excellent HOWTO. Worked perfectly the first time through.

[destr0yr]

Edit
Removing md5sum and mailwrapper from my use flags and recompiling seems to have fixed the problem. I cannot, however, mail with a user other than root.

What do you have in /etc/ssmtp/revaliases?

AFAIK, it should be:

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root:user@gmail.com:smtp.gmail.com:587
linuxuser1:user@gmail.com:smtp.gmail.com:587
linuxuser2:user@gmail.com:smtp.gmail.com:587
...

<shameless plug>http://www.destr0yr.com/article.php/Gmail_and_sSMTP</shameless plug>

[gasparov]

Hi,
I can't make it work
When I try to sendmail I can't write any body/or subject

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 echo lol|mail -v my@gmail.com -s "lol"
[<-] 220 mx.gmail.com ESMTP q13sm1257758qbq
[->] EHLO my@gmail.com
[<-] 250 ENHANCEDSTATUSCODES
[->] STARTTLS
[<-] 220 2.0.0 Ready to start TLS
[->] EHLO my@gmail.com
[<-] 250 ENHANCEDSTATUSCODES
[->] AUTH LOGIN bHVjYS5nYXNwZXJpbmk=
[<-] 334 UGFzc3dvcmQ6
[->] aWNzLjEzNzY=
[<-] 235 2.7.0 Accepted
[->] MAIL FROM:<my@gmail.com>
[<-] 250 2.1.0 OK
[->] RCPT TO:<my@gmail.com>
[<-] 250 2.1.5 OK
[->] RCPT TO:<lol@my@gmail.com>
[<-] 250 2.1.5 OK
[->] DATA
[<-] 354 Go ahead
[->] Received: by my@gmail.com (sSMTP sendmail emulation); Wed, 26 Jul 2006 18:20:50 +0200
[->] From: "root" <my@gmail.com>
[->] Date: Wed, 26 Jul 2006 18:20:50 +0200
[->]
[->] .
[<-] 250 2.0.0 OK 1153930856 q13sm1257758qbq
[->] QUIT
[<-]

As you can see two messages are sent,one is sento to lol@my@gmail.com ,the -s (even tried -S and moving it's position) doesn't work.
So I get a delivery notification on my account,the weird thing is that i don't get any mail on my account
For example this command

Code: Select all

echo lol|mail -v my@gmail.com
[<-] 220 mx.gmail.com ESMTP e16sm3775825qbe
[->] EHLO my@gmail.com
[<-] 250 ENHANCEDSTATUSCODES
[->] STARTTLS
[<-] 220 2.0.0 Ready to start TLS
[->] EHLO my@gmail.com
[<-] 250 ENHANCEDSTATUSCODES
[->] AUTH LOGIN bHVjYS5nYXNwZXJpbmk=
[<-] 334 UGFzc3dvcmQ6
[->] aWNzLjEzNzY=
[<-] 235 2.7.0 Accepted
[->] MAIL FROM:<my@gmail.com>
[<-] 250 2.1.0 OK
[->] RCPT TO:<my@gmail.com>
[<-] 250 2.1.5 OK
[->] DATA
[<-] 354 Go ahead
[->] Received: by my@gmail.com (sSMTP sendmail emulation); Wed, 26 Jul 2006 18:27:22 +0200
[->] From: "root" <my@gmail.com>
[->] Date: Wed, 26 Jul 2006 18:27:22 +0200
[->]
[->] .
[<-] 250 2.0.0 OK 1153931248 e16sm3775825qbe
[->] QUIT
[<-]

Says all "ok" but no mail arrive on my@gmail.com,so sending stuff seems to work because if i put a wrong email address after the mail command i get a delivery notification in my account but nothing is really sent,at least nothing arrives

[smdeep]

Hi
Excellent howto. Just got it working!

Thanks!
Sudeep

[mikegpitt]

Great tip... FYI this also works on gmail for domains.

[nosatalian]

I can't seem to get this to work. My config files are exactly as everyone elses, but with the most recent (~arch) and stable in portage, I get a segfault when trying to connect. With older ssmtp versions, I just get a failure "Must issue a STARTTLS command first" even though my config file is identical, and I've already specified UseSTARTTLS=YES .

I get this segfault with the newer versions in portage, after getting past this step, and I can verify that it occurs on two different machines- one amd64, and one i686. I've made sure on both that my CFLAGS are minimal.

[Cagnulein]

Little offtopic:
is there a way to store all the sent mail on a folder readable by mutt? I have already an imap server on my pc that stores incoming mail, now i want to store sent too (using my ISP SMTP server (tin.it)) . I think ssmtp it was i looking for, at least for the first target..
Thanks

[Reistlin]

I can't seem to get this to work. My config files are exactly as everyone elses, but with the most recent (~arch) and stable in portage, I get a segfault when trying to connect. With older ssmtp versions, I just get a failure "Must issue a STARTTLS command first" even though my config file is identical, and I've already specified UseSTARTTLS=YES .

I get this segfault with the newer versions in portage, after getting past this step, and I can verify that it occurs on two different machines- one amd64, and one i686. I've made sure on both that my CFLAGS are minimal.

The same problem for me. sSMTP segfaults while trying to establish secure connection. Hovewer I run the stable amd64 with very few ~amd64 packages. Core dump shows nothing about origin of the error

[Thesee]

Cagnulein: a way to store all "sent mails" sent from mutt to a directory readable by mutt could achieved by writing this in your .muttrc:

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set record=+~/mail/sent-mail

Great howto by the way! I had it working with postfix, then, for an unknown reason, it didn't work anymore, and then I discovered this, and *WHAM* it works again!

[krisse]

Everything works well when mails are sent to a complete email address (name@domain), however when trying to send to a local user "name", the mails is sent to "namegmailuser@gmail.com". That is, local username "name" is just prefixed to my gmail address.

Yes, I have a entry in /etc/ssmtp/revaliases.

The mail is sent by cron. (Sure, I can set the mail address in crontab to something else. But that's not a fix, just a way around the problem.)

[lcidw]

I can't seem to get this to work. My config files are exactly as everyone elses, but with the most recent (~arch) and stable in portage, I get a segfault when trying to connect. With older ssmtp versions, I just get a failure "Must issue a STARTTLS command first" even though my config file is identical, and I've already specified UseSTARTTLS=YES .

I get this segfault with the newer versions in portage, after getting past this step, and I can verify that it occurs on two different machines- one amd64, and one i686. I've made sure on both that my CFLAGS are minimal.

The same problem for me. sSMTP segfaults while trying to establish secure connection. Hovewer I run the stable amd64 with very few ~amd64 packages. Core dump shows nothing about origin of the error

Build ssmtp without md5sum and mailwrapper.. It's one of those, too lazy to check which one. Had the same segfaults and with only the ssl flag, it works like a baby in water.

[nosatalian]

Weeks later, this is still dreadfully broken. I've tried with every combination of use flags. I was using esmtp after I gave up on this, but that doesn't work any longer either- I get weird 0 (null) messages. I'm not sure how this is working for everyone else.