On 28 Jan 2022, at 23:02, Walter Lee Davis via TextMate wrote:

Finally figured this out. For some reason, my dock icon was linked to a copy of TM2 in my Downloads folder, and I had another copy in my Application folder. The "reload after restart" is (I presume) scoped to only work with application in the Applications folder, for no doubt good privacy- and security-increasing reasons. I got rid of the duplicated app, and now a restart includes all my TM windows.

Things you download have some extended attribute set until you move the application out of ~/Downloads and with this attribute set, when you launch the app, the system will actually create some read-only volume and run the app from there.

I have no idea what this protects us against, but it sounds right that relaunch after reboot will fail, because the instance of TextMate running (from ~/Downloads) is ephemeral with this read-only volume shenanigans.