Software versions:

ssmtp - 2.54-7
postfix - 2.9.6-1~12.10.1

I'm running Ubuntu 12.10
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I can confirm/reproduce that that in 2.3.1.

<pre>
Environment:
Operating System Debian Linux 7.1 (wheezy/stable)
Redmine version 2.3.1.stable
Ruby version 1.9.3 (x86_64-linux)
Rails version 3.2.13
Environment production
Database adapter PostgreSQL
Redmine plugins:
redmine_ldap_sync 2.0.1.devel.g7566486332
</pre>

config/configuration.yml:
<pre>
production:
email_delivery:
delivery_method: :sendmail
</pre>

I can send emails from the commandline ("echo "Subject: test" | sendmail -v user@domain.tld"). Postfix is *_not_* installed but ssmtp is.

<pre>
root@caspar:/var/lib/redmine# echo "Subject: test" | sendmail -v user@domain.tld
[<-] 220 mail.domain.tld ESMTP Postfix
[->] HELO caspar.server.domain.tld
[<-] 250 mail.domain.tld
[->] MAIL FROM:<caspar@server.domain.tld>
[<-] 250 2.1.0 Ok
[->] RCPT TO:<user@domain.tld>
[<-] 250 2.1.5 Ok
[->] DATA
[<-] 354 End data with <CR><LF>.<CR><LF>
[->] Received: by caspar.server.domain.tld (sSMTP sendmail emulation); Tue, 02 Jul 2013 18:47:19 +0200
[->] From: "root" <caspar@server.domain.tld>
[->] Date: Tue, 02 Jul 2013 18:47:19 +0200
[->] X-selfnet-root: caspar
[->] Subject: test
[->]
[->] .
[<-] 250 2.0.0 from MTA(smtp:[127.0.0.1]:10025): 250 2.0.0 Ok: queued as 46104180301
[->] QUIT
[<-] 221 2.0.0 Bye
</pre>

Because I got the test email from the commandline I think my /etc/ssmtp/ssmtp.conf should be correct.
--------------------------------------------------------------------------------
Perico Os Palotes wrote:
> Software versions:
>
> ssmtp - 2.54-7

Looks like a typo since Ubuntu 12.10 ships with 2.64-7.

> postfix - 2.9.6-1~12.10.1
>
> I'm running Ubuntu 12.10

I'm also on Ubuntu 12.10 and I have not seen any problem between Redmine and sSMTP. I'm running Redmine version 2.3.2 though.

<pre>
Environment:
Redmine version 2.3.2.stable
Ruby version 1.9.3-p194 (2012-04-20) [x86_64-linux]
Rails version 3.2.13
Environment production
Database adapter Mysql2
Redmine plugins:
no plugin installed
</pre>

So, works for me.
--------------------------------------------------------------------------------
Note: since I'm getting "422. This request was denied because it was considered spam or your IP adress is temporarily blocked." while trying to update the issue, I'll replace, as per http://www.redmine.org/issues/12495 all links and domains by redime.org.

Updated information:

1. Software versions:

Environment:
Operating System Ubuntu Server 12.10
Redmine version 2.3.2 2013-07-14
Ruby version ruby 1.8.7 2012-02-08 patchlevel 358 [x86_64-linux]
Rails version 3.2.13
Environment production
Database adapter Mysql
ssmtp version 2.64-7

2. E-mail settings ssmtp using 3rd party relay, replaced by redmine.org in this snippet

ssmtp 2.64-7

/etc/ssmtp/ssmtp.conf

root=admin@redmine.org
mailhub=smtp.redmine.org:587
UseTLS=YES
UseSTARTTLS=YES
AuthMethod=LOGIN
# 3rd party relay credentials
AuthUser=*********@redmine.org
AuthPass=*********
hostname=server.redmine.org

3. I can send e-mails through ssmtp:

echo "Subject: test" | sendmail -v destination@redmine.org

[<-] 220 mx.redmine.org ESMTP dr11sm4732360wid.3 - gsmtp
[->] EHLO server.redmine.org
[<-] 250 ENHANCEDSTATUSCODES
[->] STARTTLS
[<-] 220 2.0.0 Ready to start TLS
[->] EHLO server.redmine.org
[<-] 250 ENHANCEDSTATUSCODES
[->] AUTH LOGIN
[<-] 334 VXNlcm5hbWU6
[->] amFtZ28ub3JnQGdtYWlsLmNvbQ==
[<-] 334 UGFzc3dvcmQ6
[<-] 235 2.7.0 Accepted
[->] MAIL FROM:<local_unix_user@server.redmine.org>
[<-] 250 2.1.0 OK dr11sm4732360wid.3 - gsmtp
[->] RCPT TO:<destination@redmine.org>
[<-] 250 2.1.5 OK dr11sm4732360wid.3 - gsmtp
[->] DATA
[<-] 354 Go ahead dr11sm4732360wid.3 - gsmtp
[->] Received: by server.redmine.org sSMTP sendmail emulation; Fri, 30 Aug 2013 16:38:08 +0200
[->] From: "local_unix_user" <local_unix_user@server.redmine.org>
[->] Date: Fri, 30 Aug 2013 16:38:08 +0200
[->] Subject: test
[->]
[->] .
[<-] 250 2.0.0 OK 1377873491 dr11sm4732360wid.3 - gsmtp
[->] QUIT
[<-] 221 2.0.0 closing connection dr11sm4732360wid.3 - gsmtp

4. I tried to create a user and check "Send account information to the user", and also creating a ticket and adding this new user as a watcher. In both cases looks like redmine never reached ssmtp, since /var/log/mail.log shows no activity.

@Simon can you please provide same details of your working environment?

Can somebody else please try to reproduce?

Thanks

--------------------------------------------------------------------------------
I had the same problem running redmine 2.3.3 on Ubuntu Server 12.04. The problem seems to be the '-t' option given to sendmail. By changing the _configuration.yml_ file to
<pre>
production:
email_delivery:
delivery_method: :sendmail
sendmail_settings:
arguments: '-i'
</pre>
redmine is now able to send messages via ssmtp.
--------------------------------------------------------------------------------