ATTN: All players for "P&N on PBW, take 2"

[Suicide Junkie]

Usually. Ships will only follow an order if they can see their destination from their current location.

If the resupply depot/Waypoint was in the same system it would work. If it wasn't, you'd have to give orders to warp.

You can chain together orders, so you can have a ship move after it warps into a new system. You just have to be explicit about each leg of the journey.