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Does R2-D2 repair a shield on a green maneuver that also clears stress, and when does it happen relative to collisions and obstacles?

Yes, both happen: stress is cleared and one shield is repaired, up to starting shields, once per green maneuver. The shield comes back even if the maneuver ends in a collision, and for an overlapped obstacle it is recovered before the damage roll. Exact timing in odd cases is less settled.

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