This is an old problem at un-towered airports.
If you watch the objectives window, from the ramp it won’t trigger the “taxi up to 15kts” step, the next step being to follow the taxiway to the runway, then hold short.
I have not tested this fully since the last update, but just going through the motions as I did over the weekend, it still does not detect you take off.
Interestingly, if you then fly to another un-towered airport, taxi to parking, then request takeoff, this second flight will detect you taxiing up to speed. but never the first.
The post below I tried to list all the steps that appear in the objectives window in order, covering taxi, take off, landing, and taxi back to parking.
This is the step that does not trigger from un-towered:
But it works the second time just fine, so it’s definitely a bug, but seems to not get much interest, sadly, as it is so easy to demonstrate. It does not occur at towered airports, ever, as long I interact with ATC.
Will test again later this evening, hopefully, but I believe it is still broken.
To remove the pointer back to where you just left, the workaround is to interact with a different tower, and announce your intentions.