This is quite a long story but needs to be told in order to understand the full situation.
We are a Hotel that runs 24/7 that has a SBS 2008 Server and a Windows Server 2008 Terminal Server operating on a small LAN. Last week the SBS Operating System became corrupt. I spent hours and hours through the normal recovery appreaches to try and get the current operating system back to working order with no avail. I had no other choice and was forced to restore the server from a Symantec Backup Exec Restore point, which was taken 3 days earlier than that point in time.
I restored the OS successfully and began to notice upon logon the OS was acting very strange, it wouldnt perform normal tasks like opening MMC or clicking on start menu items. I noticed the the Microsoft Exchange Services were playing up through examination of Event Viewer. Once disabling all of these and rebooting, it fixed everything!
The only things that are important to this business are the e-mail. So, the fact the the OS had been restored to a point in time from three days ago, the only thing that would be affected (changed) is the emails. So i backed up the exchange store from the corrupt OS onto an external hdd. I restarted all the exchange services one by one after stopping them all due to system instability. Once i had restarted all exchange services and rebooted the Server, everything was fine and back to normal....for now.
I transfered over the exchange store from the external hard drive etc. and got that all up and running. Everything seemed to be fine. Then this weird problem started to occur with active sync and exchange on Apple products.
Microsoft Outlook 2007 on all workstations and laptops worked totally fine as you would expect. Emails would send and receive with no problem. Then comes the iPhones/iPad.
John and Bob were having problems with there email on apple products. We will start with Bob, who just has an iPhone. He was saying that there was problems with his account not working, so I decided to just delete the account and start again. I set up his account (and i know the credentials are correct because i tried them on my own personal iPhone and it worked and mail began to flow through onto my phone) and it would come up with verify certificate and get pass the check (sync mail, calenders, contacts etc.), then you would go into the mail application and nothing would download or sync, the circle would keep spinning and it would just hang.
John on the other hand had this EXACT same problem, on his iPhone, iPad and Entourage 2004 on his iMac. Johns would also work on my own iPhone. just not their own. which was running their email before the crash.
Funnily enough Johns account would work on Bobs phone and visa versa. Just not on their own.
I setup IMAP email accounts for them both for the time being, which seemed to work fine (send/receive, download inbox etc.), but now they are saying that it is not syncing correctly. If they send an email from outlook it will not sync and appear in sent items on their iphone.
Sounds like a right little mess going on.
The first place I would start off pointing you towards is the test site at https://testexchangeconnctivity.com - run the Exchange Activesync Test, specify Manual Server Settings and then report back the results.
You can also download a test App from iTunes "Activesync Tester" or download it onto a PC from:
If the tests pass happily and the problems still persist - can you please move either John or Bob's email account into a different mail store and then remove and re-add the Exchange Account to the iPhone / iPad. If that works - repeat with the other problem account (your store could be corrupted and moving accounts from one store to another will clean up any issues).
If that fails - or the testing fails - please post the FULL expanded results for further scrutiny.