Hey Tom,

I only recommend using the upgrade package if you're on 4.6 or above. If you're on 4.0 and  you want to upgrade to 4.8.4 - I would use the install package to overlay your file system. Back up everything first (entire file system, entire database, and copy your web.config again for good measure).

When you overlay your file system with the install package - you'll overwrite your existing web.config. (This is very important to have a back up of at all times!) Now you can use a utility like WinMerge to compare the old web.config and the new one. Update your new web.config with the machine key and the database connection string and any other customizations that you had made to your old web.config.

Also, it wouldn't hurt to re-apply the file system permissions just in case. (Application root foler -> right click properties -> security tab -> advanced -> check 2 checkboxes ("replace all...", "inherit...") and hit apply.)

Take care,

Ian

Hey Tom,

You're welcome!

1) merge the web.config files BEFORE you do kick off the installation process (the install process depends on the updated settings).
2) Yes - the upgrade will leave all of your content as it was. It's only changing core DNN "stuff"
3) Many different ways to do this - but you can set the default document to "index.htm" (move it to the top of the list in IIS) and then add a document by that name to the root of your application. This is a quick and easy away to avoid 90% of the traffic to your site. The upgrade process will only take a few minutes - so this may be sufficient.

Again, you're welcome and let me know how it goes or if you have any more questions.

Take care,

Ian