Intermittent trouble deleting, moving & sending (Exchange 2007 & iPhone 3G)

Question

Here's my setup:
I have a Microsoft Server 2008 with Exchange 2007 SP1 running at the office. Firewall forwards the following ports to the server:
25 (SMTP)
587 (SMTP Secure)
110 (POP3)
995 (POP3 Secured)
143 (IMAP)
993 (IMAP Secured)
80 (Ahsay Backup Software)
8080 (Alternate HTTP for IIS 7)
443 (HTTPS)
6001-6004 (RPC over HTTP, for Outlook)
Exchange Server is running fine and has a self-signed certificate. I've installed this certificated to client PCs and they all connect to Outlook just fine. OWA is working fine as well. I even went as far as installing the certificate on the iPhone.
The iPhone fails at auto discovery, but that's probably because I never set it up correctly in the server. It then asks for the server, and I give it and specify SSL set to "ON" and the connection seems to be fine. Running 2.2 firmware on all of our iPhones and PUSH email via the Exchange server works great.
The problem comes when users try to delete emails, move emails to another folder, or send emails. I believe deleting a message is the same as moving a message to another folder, so I guess I only have 2 problems. Moving messages and sending messages. I can receive messages just fine. I've tried multiple things, from reconfiguring the mail settings, hard reboots, and even factory restores. But, the problem remains. Sometimes I'll have to delete a message or a group of messages 3 or 4 times before it will actually delete. The message that appears says it's unable to move the message. This had been happening for a few months now, but I just now got time to look into it.
I've hooked one of the iPhones up to Apple's iPhone configuration utility. I put the device into airplane mode and turned on WiFi, that way I would be on the internal LAN in order to rule out the firewall and a bad signal or faulty internet connection. With the iPhone connected to a wireless router and that same router wired directly to our server, I get the same results I get from remote location's WiFi network or the 3G network. Sometimes messages will send or delete immediately and other times it will take 3, 4, 5 or more tries. While in airplane mode, and the device attached to the same LAN as the server, I tell the iPhone to delete a message in the inbox, and this is what is output to the console:
Wed May 27 18:52:00 unknown MobileMail[52] <Warning>: ERROR: The message could not be moved to the mailbox Trash.
Wed May 27 18:52:00 unknown MobileMail[52] <Warning>: connection died with error Error Domain=NSURLErrorDomain Code=-1005 UserInfo=0x43dc6b0 "lost network connection" 0x43d1410
Wed May 27 18:52:00 unknown MobileMail[52] <Warning>: ASMoveItemsTask failed: Error Domain=NSURLErrorDomain Code=-1005 UserInfo=0x43dc6b0 "lost network connection"
Also, here is some more logs from earlier when I was messing around trying to delete and check for new mail. I would delete the message and then immediately hit the refresh button in the bottom left of the mail application:
Wed May 27 18:41:03 unknown MobileMail[52] <Warning>: connection died with error Error Domain=NSURLErrorDomain Code=-1005 UserInfo=0x43a8420 "lost network connection" 0x436a000
Wed May 27 18:41:03 unknown MobileMail[52] <Warning>: ASFolderItemsSyncTask failed: Error Domain=NSURLErrorDomain Code=-1005 UserInfo=0x43a8420 "lost network connection"
Wed May 27 18:41:03 unknown MobileMail[52] <Warning>: error syncing folder: Error Domain=MFMessageErrorDomain Code=1041 "Operation could not be completed. (MFMessageErrorDomain error 1041.)"
Wed May 27 18:41:05 unknown MobileMail[52] <Error>: MobileMail(52,0x8f5600) malloc: * error for object 0x4902188: pointer being freed was not allocated
Wed May 27 18:41:05 unknown UIKitApplication:com.apple.mobilemail[0x7ff8][52] <Notice>: MobileMail(52,0x8f5600) malloc: * error for object 0x4902188: pointer being freed was not allocated
Wed May 27 18:41:09 unknown dataaccessd[55] <Warning>: connection died with error Error Domain=NSURLErrorDomain Code=-1005 UserInfo=0x320330 "lost network connection" 0x3851b0
Wed May 27 18:41:09 unknown dataaccessd[55] <Warning>: ASPingTask failed: Error Domain=NSURLErrorDomain Code=-1005 UserInfo=0x320330 "lost network connection"
Any ideas on what could be causing this problem?
Thanks in advance!

Answer 1

You don't need to subscribe to experts exchange in order to read the solutions; only to post. If you scroll down all the way to the bottom, you should be able to see what was said... Either way, here's a copy of what I said:
On Expert's Exchange, Andrew wrote:
So I just reconfigured our entire server. Ended up putting the domain controller on a separate computer than the Exchange 2007 install. Both computers are running Server 2008. Had lots of trouble getting it setup correctly however. In the end, the problem I was describing above has been fixed. Here are the things I did differently this time around:
1) Instead of installing Exchange 2007 directly on the domain controller, I installed a second copy of Server 2008 on a second computer, ran the steps necessary to give Exchange access to the Active Directory on the domain controller, and installed Exchange 2007.
2) Before, I was using a self-signed certificate. Other than the fact that it was much harder to setup email on client computers, it seemed to be working fine, except on Windows Mobile devices. This time around, I got a GoDaddy UC certificate and installed that on the exchange server.
3) Another big problem I was running into was getting Outlook Anywhere to work. I finally narrowed it down to a Microsoft bug. The fix was to disable TCPIP v6 and also add a registry entry to disable it via the registry as well. After doing so, the website https://www.testexchangeconnectivity.com no longer complained about not being able to ping port 6004. I'm not sure if this has anything to do with my original problem on the iPhone, but it is something I did differently this time around.
That's all I can remember for the time being... With my new setup, however, my issue has been resolved and I'm very relieved.
I have a collection of hyper-links I kept each time I found information on the web that either helped solve a problem during my new setup or ones which I thought might help me understand the way things work. If you've exhausted all other resources and just can't seem to get things working, I guess you could skim over these:
http://www.computerperformance.co.uk/exchange2007/exchange2007_install.htm
http://www.exchange-genie.com/2008/02/configuring-outlook-anywhere-for-exchange- 2007-sp1/
http://www.experts-exchange.com/Software/ServerSoftware/Email_Servers/Exchange/Q23014474.html#a20448818
http://msexchangeteam.com/archive/2008/06/20/449053.aspx
http://www.simple-talk.com/exchange/exchange-articles/deploying-exchange-2007-on -windows-server-2008/
http://blog.sembee.co.uk/archive/2008/05/30/78.aspx
http://help.godaddy.com/article/4877
Good luck!