The iPad syncs quite well with the default applications on a Mac such as Mail, iCal, and your address book.  But you don’t have to have a Mac to enjoy the benefits of syncing.  You can also sync with Outlook on your PC.  There are, however, a few things to know before you do this since there are some issues syncing your iPad to Outlook.

The Errors And Issues

When you attempt to sync your iPad with Outlook you might get the following:

• You see an error saying that AppleMobileDeviceSync has stopped responding
• The sync completes but nothing actually happens

The “techie” issue here is that there may be some older files on your computer related to OpenSSL that are included with other software you have installed, but which causes conflicts.

The Resolution

The following files on your system (and in the following locations) are the ones that are causing the issues

• LIBEAY32.DLL or
• SSLEAY32.DLL

Do one of the following:

• Check for an update for the software that installed these files.  As long as you are using the most recent versions of these files, iTunes will sync.
• Rename the files in the above locations (for example, rename LIBEAY32.DLL to LIBEAY32.OLD).  This may cause other software you have installed to not work. In this case you can rename the files back to their original names and update the software.
• Install the latest version of files from the OpenSSL Project
• If you have a Mac, you can copy the two referenced system files from your common files/apple directory to your windows/system32 folder, restart Outlook and it should begin syncing

Some users have mentioned this set of options as solving their iPad syncing with Outlook issues.  However, your mileage may vary and since everyone’s system is different it is hard to give one exact fix.  Let’s hope that iOS 4 for the iPad fixes these Outlook syncing issues.

Did any of these help you with your Outlook sync issues?