Here are the steps I take when upgrading DNN:

1. If running an older version (i.e. 4.x), first upgrade to the latest version released (i.e. 4.9.5)
   1. Download the latest Upgrade Package of the given DNN version
   2. Stop the Site
   3. Make a Backup of the files and Database
   4. Copy the files over the current installation
   5. Check for differenced between your Web.Config and the new Release.Config
   6. Update the Web.Config if needed (do not change your database connection information, machine keys, etc)
   7. Start the site
   8. Browse the site to kick off the upgrade
   9. Test
   10. If ok, move to step 2 below
   11. If fails, roll back and try again
2. Download the desired version DNN 5.1.4
3. Stop the site
4. Backup the Site Files and Database
5. Copy the new files over the existing installation
6. Check for differences in your Web.Config and the new Release.Config
7. Start the website
8. Browse the site to kick off the upgrade
9. Test
10. If all is well, Make another backup of Files and Database
11. If failed Roll Back and Try again.

This is how I tackle this...

Best Regards,

Robert J Collins | Co-Founder & President

Netlogic Corporation

Thanks everyone for these steps.  My problem is step 5 in the procedure listed above.  Simply copying over the files from the upgrade .zip file immediately wipes out my database and a couple of other key files and replaces them with whatever is in the upgrade package.  This is the part that I keep getting stuck on - it doesn't seem like a straight copy of the files from the upgrade package is right if it just steps on the database.  I know I could just restore the database from backup but I'm worried that other key files I'm not aware of is being overwritten when I do the copy.  What am I missing?

Thanks very much for all your help so far.

-eLindy