I had the same situatuon on my Mac Book Pro 2012/Mountain Lion and run Parallels 8 with Windows 8. The time/date on Outlook is dependant on the Mac core time, which for some reason, being set to default Auto, seems to lag, presumably following Cupertino time when I am located in SGP +8 hours ahead GMT. My solution was switching off the auto time update/synch. I manually switch it on now and then just to ensure the time is synch to local Internet time. No trouble since.
Tried turning off the auto time update but no help.
The system time is correct and all other appointments are synced correctly, it's just whole day events that it messes up.
I even did 1 minute appointments that sit hard up to 12am and 12pm, these were correctly synced as well as appointments starting at 12am and finishing 12pm (so effectively all day events) which were also synced correctly.
The moment you set the "all day" feature in either outlook or the iphone it stuffs it up.
So far haven't heard a peep out of Apple about the problem and now know of at least another 5 people with exactly the same issue.
Nearly 10 months and now on IOS7 and Itunes 11.11
I and many others have submitted feedback and asked for support from Apple a number of times.
Not one single reply at all from "support"
Apple support is a bit like the fabled unicorn, just a myth, a story spun to keep the children quiet.
If they can't even be bothered to fix it in a brand new IOS then fat chance they will ever do anything about it.
With the new IOS looking like something my 5 year old made with her crayons and no support for anyone who actually uses this thing as a tool its pretty obviose that Apple are only interested in making childrens toys and the teenage market.
Hi Boneart - I feel for you.
I too have the same issue (Feb 2014) which I have just discovered today as I am not a strong user of all-day events, until today when I tried to schedule annual holidays in my diary. I can confirm the EXACT SAME issues that you have described with all-day events displacing 24 hrs EARLY for sync Outlook to iOS calendar, and all-day events displaced 24hrs LATE for sync iOS calendar to Outlook. I also confirm that the issue does not exist for specified time appointments, as you also found.
I note from several other discussion threads that Apple have previously focussed on an issue of all-day events syncing to span 2-days; that is not yet apparent in my situation BUT I will be watching with interest whether a subsequent synchronisation causes the displaced dates to also synchronise back providing the same event apparently spanning 2 days but ACTUALLY existing as two events with identical properties on successive days.
One oddity is that I also operate in the NZ time zone; I wonder if that is significant???
For a brief period I trialled iCloud with a thrid-party patch to resolve the native iCloud issue of not providing 2-way synch with Outlook. That worked beautifully ... until Apple provided an update to the iCloud interface which destroyed all functionality for me. I'm back to hard-wire sync via USB wire again. Very frustrating!!
Finally it is sad that Apple has no interest in these issues. It strikes me that as soon as there is a non-Apple platform involved they blame the other system and wash their hands of it.
iPhone 4; iOS 7.0.6 (latest); Outlook 2007 & iTunes 220.127.116.11 on Win7Pro 64x v6.1