@david_chisnall I like your point about corp/org migrations. Another advantage to transitioning programs first is, once that happens it becomes possible for others in the org to use another OS and still engage with others without needing all sorts of workarounds.

It is also the easier migration to do in my experience. The hard migration is usually IT & Security, who are quick to throw out words like: "No", and "Impossible", and also happen to usually be in a position to more or less veto such initiatives. In a Windows-entrenched environment, IT probably does not know how to deploy Linux across the org, much less support it. They also often have a lot of networking tools, telemetry, management engines etc that are Windows-specific, and depending on how hard they lean into corpo-spyware mess there may be no viable Linux alternative.

But by going applications-first, one by-steps all the fights with IT & Security. At worst, they just have to white-list a few more apps.