Here are some helpful suggestions to consider when deciding on your sync solution:

  • Before you try any sync solution, I suggest you back up your Outlook data file.  If  you want to do this manually, About.com has a good article with pictures indicating how to accomplish this here.  For Windows XP and Vista users, you can use this Outlook 2002-2007 data file backup solution from Microsoft here with another help article for its usage from Microsoft here.  For Windows 7 users, the program should work if you are an administrator.  The backup solution does work with the 32 bit edition of Outlook 2010, but you must first apply the fix from Microsoft located here.
  • There are a few solutions that are rock solid and some that do not have many complaints.  Exchange and Google Apps are rock solid.  CompanionLink, Sync2, gSyncit, and MyPhoneExplorer are also good solutions.
  • Many sync problems are not due to bad software, but corrupted Outlook data files.  If you want to eliminate some possible problems before you start, please go here for instructions on scanning and fixing your Outlook data.  I am not affiliated with them, nor do I endorse any products there.  They just have a good description and pictures of how to repair your data file.  The free program provided by Microsoft that you will use is SCANPST.EXE.  There are websites that will try to convince you that you need to buy something to fix your data file.  Do not be taken in by their marketing schemes.
    • Feedback from Daniel: After doing the fix that you told me about ... I was able to get gSyncit to work through Outlook to Gmail and update the Droid with no problems. ... Thanks again
  • Remember, many of these sync solution providers have been in business for years and have quality and tested products.  It is more likely that your data is the problem than their software.
  • If you have experienced duplicated contacts and calendar items and they are now out of control, I suggest the following (when I have more time I will go into more details, but even then they may differ from Android to Android):
    • Back up your Outlook data file.  If you have a previous backup, do not overwrite it.  This is only a precautionary backup.
    • Exit Outlook and uninstall the sync software.
    • If you are using Google's services for Calendar and Contact sync, turn off the sync for these items on the Android.  Then go to Google and clear out the calendar and contacts.
    • On the Android, delete all Calendar entries and Contacts.  There are commands to clear them all out.
    • Restore your old Outlook data file if one exists.
    • Start Outlook and fix your Calendar and Contacts if no backup was available from which you could restore.
    • Now you can continue with installing sync software.
    • If you are using Google's services for Calendar and Contact sync, you may turn on the sync for these items again on the Android.
  • If you have a large number of contacts and calendar events to sync, I do not believe any program will sync your data quickly or without errors.  Your only good solution is to use a hosted Exchange service.  An example would be Exchange 365 reviewed here.  You must pay for this service.  A low end service like Microsoft's Exchange 365 will be only $4 per month, while a more encompassing service may be $20 per month.  How much is a large number of contacts?  A customer of mine has 1,250 contacts and has everything in her day planned in her calendar.  Gsyncit took a long time  to perform each sync.  Exchange 365 is instant.  A visitor with 14,000+ contacts and 21,000+ events complained that CompanionLink was doing a bad job syncing, although he admitted nothing he tried worked right until he used Exchange 365.  He said everything is instantaneous with this service and he is quite happy to pay for his solution.