IIS 8.5 URL Rewrite just wont work: rules have no affect at all
It turned out that under the sites SSL settings the "Require SSL" checkbox was checked. If this is checked the client cannot get through on port 80 at all and the rewrite never happens...
If you are using the rewrite module you cannot have "Require SSL" checked as the initial request needs to be able to get through on port 80.
Well, I thought I ran into the same case as MrLane on IIS 8.5.
It took me day to find out that I had not have the website running on the port 80.
I just add this binding (port 80) and the rule work as expeceted.
Hope this can help to solve MrLane's case.