I also ran across this not too long ago - Have not tried it yet, but it
looks very similar to Doug's solution:

http://gist.github.com/72916

Dave

2009/3/21 Doug Bryant <doug.bry...@milemeter.com>

> We have been using google apps for smtp email for almost a year now in
> development/test/production environment.  Never gives us a problem unless
> gmail is down.
>
> Attached is the smtp tls extenstion which is required to send with google
> apps.  Below is our smtp_config.rb with the sensitive setting changed.  I
> place both in <our_app>/config/initializers/ directory.
>
>
> ActionMailer::Base.delivery_method = :smtp
> ActionMailer::Base.smtp_settings = {
>   :address => "smtp.gmail.com",
>   :port => 587,
>   :domain => "some_domain.com",
>   :authentication => :plain,
>   :user_name => "usern...@some_domain.com",
>   :password => "****************"
>  }
>
>
>
> On Sat, Mar 21, 2009 at 4:52 AM, Shaolo <ot...@shaolo.com> wrote:
>
> > I've been struggling with this for many hours.
> > Problem:  I'm trying to get action mailer to use a google apps email
> > address
> > to send email to other google apps email addresses.  The server the app
> is
> > running on is not configured to send email to other machines.
> >
> > There is no debug output to speak of looking through server system logs,
> > and
> > the /logs directory of the app.  Has anyone managed to get google apps
> > email
> > working with the action mailer plugin?  I've found like 7 different
> methods
> > for enabling TLS and I've tried them all and none have worked.
> > I believe I have a "working" site configuration based on:
> > I had it setup to use sendmail (which my server does not use) and noticed
> > that it was failing appropriately since the server is not setup to send
> > email to other domains.  So it looks like the site page works OK (body,
> > mailer, email sections), it's just a matter of getting the action mailer
> > extension setup so it will use a TLS mailer plugin and login
> appropriately.
> >
> > I HAVE tested the user account through Entourage and it works fine.
> >
> > Has anyone else done this... successfully?
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