Waypoints to attack targets work inconsistently

You can use shift to do waypoints on enemy targets to have your units attack those, as Survivalist shows in this 1 year old video: https://youtu.be/aOzudiQ5Jcs?t=562

I wanted to try this myself, but somehow waypoints on targets only work sometimes, but othertimes not. I used the editor to test it out and got this result:

It does work if your units have a movement order as the first order in the queue, or if the first target is ~4 tiles out of range.

It does not work if the first target is in range+~2 tiles. Then the waypoints dont appear and your units immediately target the last clicked target, as if you werent holding shift.

I tested this with archers attacking melee units that were stuck between some palisades.

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Does this happen to other players too? As multiple patches contained small changes to the waypoint system, it might be that this bug got in at some point and wasnt there when Survivalist made the video.