We are still engaged with Microsoft since December of 2014, to try to troubleshoot this e-mail delay - non delivery issue. Since my last post we have confirmed reports of this issue "Exchange e-mail is not delivered to iOS 8 device until a manual sync / step is taken" in other organizations which are not Office 365 and just running exchange 2010 on-premise. Here is the first response I have gotten from Microsoft with anything looking like a root cause. Our Premier support specialist replied with this, which he said he got from Microsoft's internal Apple team.
“There is a new feature in iOS 8 where the device protects
against a Ping/Sync loop. If Exchange responds to 3 consecutive Ping requests
with a status of 2, and then does not send any data in the corresponding Sync
request, the device will “black list” that folder and not attempt again until
the user manually syncs the folder.”
This "Sounds" exactly like our issue. I am still trying to catch the problem in our lab with iOS 8 devices setup to route through a PC running Fiddler tracing.
My question is - even if I catch the above mentioned behavior - what am I supposed to do about it?