Exchange 2003 ActiveSync issue with iPhones

Hello,
    I am having an issue with an Exchange 2003 server, where a couple of iPhones can suddenly no longer Activesync with it. It seems to be an issue with their specific accounts. I set up an account for myself and was able to connect
and sync with no issue from my Windows 8 phone and also the Remote Connectivity Analyzer.
   However, with the iPhone user I tried to run his account through the Analyzer and got a timeout error when it was testing to sync the inbox. I also tried setting up the user's account on my Windows phone and the inbox just showed "syncing,
this could take a while" and just kept doing that.
   The mailbox in question is pretty large, the System Manager shows it at 41GB and I think that may be the issue. However, initally the user told me that the phone worked fine until about a month ago. When I first started troubleshooting
the issue, I found that the self signed certificate had expired around the time the phone stopped syncing and generated a new one. But I think the user had tried to wipe the account and re-set it up normally but that wiped any mail that was on the phone
and now it is trying to resync a large amount of data and that is causing the timeouts.
   I have also been reading that Microsoft Security Essentials can cause these types of issues and it is installed on the server, but would it cause these issues with only certain accounts or with iPhones but not Windows phones?
   Am I on the right track with this? Thanks.

The event viewer shows no ActiveSync errors for the user. I tried to connect to the account from my Windows phone and it set up ok with no errors (the user tells me that the account setup on the phone went ok too, all green checks) but when it was
doing the initial sync, it just seemed to hang with a message saying something like "syncing, this could take a while" or something to that effect.
The Remote Connectivity analyzer came back with a timeout error for the Inbox sync step as well.

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