Leopard Mail server, dual delivery with Google Docs

My advance apologies if this topic has been discussed before:
I work in education and would like to start using google docs concurrently wtih the mail services we already use (a semi-customized version of the standard Leopard Server mail packages).

As I understand it, this project has 3 different pieces.
1. DNS - MX records need to be setup so that Mail is delivered to both my local servers and to the google servers.

2. Import/Export of Existing OD users, groups and passwords (I've got about 500 users and 80 or so groups.) This seems to be the hard part. I've looked at the documentation posted on Google's site, but everything is bent to help AD users.

3. ODM user password sync once initial import is done. We're trying to move to a place where we're using a single sign on, and we've gotten it down to 2 working password servers. This is confusing for many of our users and I'd like to avoid adding a third password for them.

I realize this topic covers DNS, OD and Mail but I'm hoping to get advice from some of you out there who may have either already done this or tried and decided to do things another way.

I plan to cross post to the Google Docs forums and see if anyone there has attempted what I'm trying to do.

Thanks in Advance,
David Peterson
Systems Administrator
Sunnyside School District
Sunnyside, WA

MacPro, Mac OS X (10.6.2)

Posted on Dec 14, 2009 10:06 AM

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Dec 14, 2009 10:12 AM in response to dptech

1. DNS - MX records need to be setup so that Mail is delivered to both my local servers and to the google servers.


MX can't and won't do this.

MX records set a list of mail servers that are responsible for your domain's email. You can list multiple servers, and can even set priorities, but remote mail servers will only send mail to one server, not two.
The point of having multiple MX records is for fallback - the remote server will try the highest-priority mail server first. If that fails it will attempt to send the message to the next-highest priority mail server, repeating until either a mail server responds or the message goes through.

The only way to get double-delivery like you describe is to have the message come into your server, and configure your server to deliver a copy of the message to Google in addition to storing it locally.

2. Import/Export of Existing OD users, groups and passwords


Can't help here, sorry.

3. ODM user password sync once initial import is done


Or here, either, although I'm guessing this is tied to the above.
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Mar 3, 2010 10:48 PM in response to dptech

I wondering if you ever found the answer to this problem. I'm hoping to evaluate Google Apps prior to migrating our mail services to Google's control. I'm hoping to find a step by step solution as I'm not a mail admin and don't what to leave anything out.

Greg Busch
Director of IT
Salem Lutheran School
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Mar 10, 2010 1:30 PM in response to gbusch

The easiest thing to do, if you want to try a few users switching completely to gmail, is to go into Workgroup Manager and change the mail settings for that user to forward to the gmail account. You should have a "test domain" from google that you can use as an email address (something like user@example.com.test-google-a.com but where "example.com" is your domain, obviously).

If you have some method of writing sieve filters, such as the Avelsieve squirrelmail plugin http://squirrelmail.org/plugin_view.php?id=73 you can use that to create a rule that forwards a copy of the messages to gmail while keeping a copy on your server, so you get delivery to both simultaneously. But this is still a per-person setup.

To get simultaneous delivery for all your users at the same time, you'll need to get into editing your postfix settings by hand. It's probably not worth the bother. A mistake can completely ruin your mail delivery, so it's actually safer to simply switch to gmail entirely, unless you really know your postfix.

Google suggest a couple of strategies in their documentation, you should look through that and choose the method that you're most comfortable with.
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Mar 29, 2010 7:36 PM in response to Joseph Delaney

Just a quick add on from my experience:

I was using the squirrelmail filter to forward mail to my google apps subdomain and was getting dropped emails randomly.. turned out out internal email server was not able to see (resolve) the external MX records pointing to our Google Apps subdomain.

The only solution I found was to put an external dns in the network settings on the server so that it could see the MX records.. that worked fine but then the squirrel mail filters stopped working, because the server no longer was able to resolve the internal webmail component.

Every other piece os squirrel mail works.. just not the filters.. when you click the link you get this error: Could not log on to timsieved daemon on your IMAP server mail.myhost.org:2000.
Error Encountered: 60 Operation timed out

So I'm still stuck trying to make dual delivery work.

For now the only thing to do is just forward all mail to Google Apps while we transition, which is ok because we are committed to going that direction.

Not sure why leopard mail doesn't have a 'leave copy on server' check box in the forwarding field on Workgroup manger??

Anyway my .02

If anyone has a fix for filters not resolving, point to an IP? that would be great.
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Leopard Mail server, dual delivery with Google Docs

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