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Pretty much impossible for me to do as the software is 3rd party. Heck, one still needs to run on Windows 2008 and another just stopped requiring IE6.

[edit]my own programs are macOS and iOS - so no experience on Windows programming in 10 years[/edit]

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So many US schools use Apple products and/or Chromebooks and/or Android, I would have thought that approach was already unsustainable. It can hardly be essential software, can it?

We are fine with Apple (enterprise deployment of custom stuff is a known scenario). I would expect a lot of schools wouldn't have a Chromebook problem[1] given elementary schools are different beasts than BIE schools or colleges. We have some additional software because of agreements related to text books and training videos plus specific contractor provided software for grants.

1) well except for one they might not be aware of https://www.eff.org/deeplinks/2015/11/guide-chromebook-priva...

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