Q: Calendar syncing issues

Do you have iCloud Control Panel installed?

http://support.apple.com/kb/dl1455

Or if you want to sync through iTunes on Windows machine

http://support.apple.com/kb/TS2776

If it's an Exchange account, syncing will not work.

I am running MS Outlook 2010 and I am not able to sync my Outlook calendar with my iphone or ipad.

Is this on a Windows PC? If so, by any chance do you have Eset security software installed on the PC?

If so, there's a couple of alternatives.

Either try the procedure in Samoreen's post:

Re: iTunes 11.1.4.62 freezes while syncing with Outlook

Or, see if you can get hold of the Eset beta addressing the problem. As Samoreen notes in another post:

ESET have a workaround for this issue. They gave me access to a test version of the HIPS module and this fixed the problem. So I could re-enable the ESET_OPTIONS environment variable (although I still consider that it's a questionable idea). I upgraded to iTunes 11.1.5.5 and there was no problem.

 

So maybe you should get in touch with ESET support and request the new module ? Just send a message to Marcos in the ESET forum.

Re: Outlook 2013 Calendar Sync fails with new iTunes 11.1.5.5