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So when moving multiple squads through terrain are you allowed to roll for them all then move them?

The way I read the rules you roll when moving a unit and you move them one at a time, so terrain checks cannot be rolled for them all before you start moving.

You have to roll for each squad individually. You can roll for them all and then start moving.

Well, by the rules, you have to complete one unit's movement before going to the next unit, and cannot go back to a unit after starting another unit's movement. The difficult terrain roll is part of that movement, so you should do one unit at a time.