Exchange 2003 to 2007 transition

We are trying to migrate our email server from exchange 2003 over to 2007 as the first step in our move to exchange 2013.  So far, everything has been pretty smooth.  I believe that the new server is all configured based on that fact that the ExchangeActiveSync works when I point my phone at it, and I am able to both send and receive mail through it on my phone.  The autodiscover service is not working, but I'm not sure if it is worth my time to get that working for 2007 because if all goes well, we'll be on 2013 in less than 2 months, and we do not use Outlook Anywhere yet.  I have not yet moved any mailboxes, because I want to make sure that no mail gets lost, and mail will still be delivered to the new server.  To verify that, I created a new user with a mailbox on the new server, and sent it a few messages.  The test account will not receive any emails.  The test account CAN SEND, but can not receive.  We do have an email security appliance that acts as the initial point of contact, and a nat rule that directs OWA traffic, but I do not think we have any firewall settings that would block mail flow from the appliance to the exchange server.  Has anyone seen anything like this?  Likewise, does anyone think it is worth configuring the autodiscover or would you also skip it?  Looking forward to hearing any insight you may have.
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GileadITAsked:
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Scott CSenior EngineerCommented:
I would go through this 2003 to 2007 guide to make sure you didn't miss any steps.

http://exchangeserverpro.com/exchange-2007-transition-guide/

You're going to want to look at section 4 which is Migrating Email Routing.  

I'd get Autodiscover working as you will need it in the future and you don't want to move onto the next phase of your project with a known issue.
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Simon Butler (Sembee)ConsultantCommented:
Autodiscover isn't really an optional feature.
It is not only used for profile creation, but the client queries it regularly for updated information, but also when setting Out of the Office and doing availability queries. Therefore you need to get it working.

Number one reason is lack of trusted SSL certificate on the server.
Second reason is having the URLs configured incorrectly. Unlike Exchange 2003, which didn't care what address you used, Exchange 2007 and later is very specific and it needs to done correctly.
If you don't have a trusted certificate, then get one. If you get the certificate with generic names then it will work for your migration to 2013 later:

mail.example.com (common name)
autodiscover.example.com
legacy.example.com (used for the migration phase between 2007 and 2013).

Simon.
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GileadITAuthor Commented:
That's the guide I've been using actually.  Sadly, we do not use an ISA server as our firewall, so that guide is of little help considering I've checked and double-checked everything that it says except for the ISA server config.

Not configuring an optional component wouldn't be considered "a known issue" in my mind.  But, since you have a suggestion, do you know if the autodiscover for 2007 and 2013 would overlap at all??  Because if so, then I would only want it to work for 2013.
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Simon Butler (Sembee)ConsultantCommented:
Autodiscover is not optional and not version specific.
You can have clients on any version of Exchange later than 2007 hitting any server and getting the correct Autodiscover information.

Simon.
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GileadITAuthor Commented:
Thank you for your comments, even though they weren't overly productive.  I managed to get the Autodiscover working by configuring the internal and external Url's for the virtual directory with the Set-AutodiscoverVirtualDirectory and that was the missing piece for autodiscover to work.  (honestly though, if I can connect a client without that working, how is it not optional???  Can you explain that Sembee or did someone just tell you that it wasn't optional and you spread that around as best you can?  Truly just curious here.)

I also got the mail flow working.  I'm not sure if I indeed needed to do this step, but I deleted and recreated the routing group connectors.  Then I directed the incoming mail to go to the 2k7 server instead of 2k3, and I deleted the SmartHost from the 2k3 SMTP Virtual server. I had done that a few times already, and tried to test after the change was made, but mail was not flowing reliably and I didn't want a prolonged delay for my end users, so I always changed it back within the hour.  Finally, I stumbled on one guide that said all the same stuff as the others I had read, but came with the final, most important step of restarting the SMTP and the MS Exchange Routing Engine services (which I should have known to do on my own really...)  But then it all worked as I was expecting it to.  This will be the answer for my question.
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GileadITAuthor Commented:
I was the only contributor who provided valuable information about how to resolve the issue.
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