Running latest galaxy wearable app - 2.2.24, with S10 5G
100 percent replicatible. Clearing wearable app cache / reinstallation does not resolve issue.
When the phone is restarted, all app listings and subsequent notifications in the work partition of the device are lost - see screenshot 1 below for the lack of gmail work app (gmail with a small briefcase icon).
If you clear the app data after the watch is unlocked for the Galaxy wearable app and reset the app, the work apps now show up (note the briefcase gmail version in the screenshot below) until the next reboot.
I am speculating that the Wear app is starting before the work container is unlocked, therefore simply removes the apps from the list, rather than retrying once the phone has been unlocked for the first time. This needs to be resolved. I am happy to debug with any engineers, but I can replicate this consistantly with the above steps.