Our policy is set to place the ProgressScreen.app file and the HTML file we're overriding it with and then immediately run this python script. The script correctly sets the build time, hidden status for the quit button, etc. However, it will not change the page pulled up until you run the script with the exact same settings a second time. Once it's run that second time, it updates the page to show the HTML file we're overriding the default with.
The most annoying thing about this issue is that it only happens on enrollment. The exact same policy put in Self Service works perfectly everytime.
(Edit) Specifically this is in the ProgressScreenHelper. Just realized the Issues page was for all of your scripts and not just that one.