Hi all! I'm the maintainer of the jss-filevault-reissue workflow referenced above, and I've got a quick update that may be of interest to you.

My team has published a new tool called Escrow Buddy, which regenerates FileVault keys at the loginwindow, thus avoiding the need to prompt users for their password later. It should be suitable as a drop-in replacement for my previous jss-filevault-reissue workflow at most organizations.

You can read more in this announcement on the Netflix Tech Blog, and this post on my site specifically covers migrating from my old workflow to Escrow Buddy. Escrow Buddy's source code and installer are available on GitHub.

Thanks!