I found lots of people with this problem -- Droid 2, exchange email, emails stuck in their outboxes. AND people with Droid 2 complaining that they could only get their emails if they went to the client and hit refresh -- data push didn't work. I had both of those problems -- plus, the 15-minute fetch wouldn't. Only got emails when I went to get them myself by hitting refresh.
I found few answers, but I think I might have just figured it out. Maybe.
I have admin access to my Exchange 2003 server. I looked at the event logs, and saw that every 2 seconds, the server was generating an error with Event ID 3005. I found that if I turned off data push on my phone, these errors stopped. I then ran some google searches on Event ID 3005, and eventually landed on making these 2 changes on my server (which is actually SBS 2003):
1. Within IIS, I expanded SERVER_NAME\Web Sites\Default Web Site. (This is the web site that has all of the Outlook Mobile Access, ActiveSync, etc.) I went to the Properties of Microsoft-Server-ActiveSync, Directory Security tab, and then the certificate settings, and I unchecked the "Require secure channel (SSL) setting for this directory.
2. Then I went to the properties of the Default Web Site. I had IIS set to respond with this web site for these 3 options:
Port # IP Address Header
------------------------------------------
Port 80, <particular IP address>, internal.domainname.com
Port 80, <particular IP address>, internal.seconddomainname.com
Port 443, <all unassigned IP addresses>, <blank header>
I added a fourth one:
Port 80, <all unassigned IP addresses>, <blank header>
3. At a command prompt, I used IISRESET /RESTART to force all Internet services to restart.
When I turned "Data Push" back on, on my Droid 2, Event 3005 errors were not being generated anymore -- but more importantly, I was immediately notified of emails that had come in while I was monkeying with this.
I'll point out that the settings I had used before were the same ones I used with "push" email on Windows Mobile 6, Windows Mobile 6.5, and my Droid 1. I'm not sure why the Droid 2 would be any different, but ... at least it's working for this moment.
I appreciate everyone else's tips, so I wanted to share this, in case it solves anyone else's woes.
B.