Interesting question.
There's a crystal clear answer and a not so clear answer depending on two scenarios:
Scenario 1: A ship stops on an obstacle, and on its next movement it's maneuver template is partly overlapping the obstacle the ship stopped on. This results in a second roll for potential damage, with no room for rules dispute.
Scenario 2: Here's where it's a bit more confusing. Let's say a ship stops on an obstacle, but only the "back end" of its base is on the obstacle. In the ship's movement next turn, its base will still be (partially) overlapping the obstacle but the maneuver template will not be. This is where it gets curious.
According to moving through obstacles:
"When a ship executes a maneuver in which either
the maneuver template or the ship’s base physically
overlaps an obstacle token, follow these steps:" (rulebook pg19)
So we need to check what it means to execute a maneuver:
"Execute Maneuver: Holding the template
firmly in place, grip the side walls of the base
and lift the ship off the play surface. Then place
the ship at the opposite end of the template,
sliding the rear guides of the ship into the
opposite end of the template." (rulebook page 7)
So, the question is, does the ship's base at the starting point count as part of the maneuver execution? Since the definition of executing a maneuver is picking up a ship and moving it to its new location, I suppose there's room to argue that perhaps the starting place of a ship's base is ignored (ie the execution of a maneuver only begins once the ship is lifted from the table). If this is the case, there wouldn't be another roll for damage if the maneuver template and stopping point of the second movement didn't overlap the obstacle.
BUT, both the picking up and placing down of a ship seem to be part of executing a maneuver, so I suspect that if a ship stops on an obstacle then its next movement will still require another roll for damage even if only the ship's base pre-moving overlaps the obstacle (but the man. template and ship base at the end of the move don't overlap any obstacle). Since the definition of executing a maneuver references both picking up and putting down the ship, I think that the ship's base-before-movement is included in maneuver execution, and is therefore relevant for determining obstacle overlap. So this is how I would rule it, based on what the rules say.
There's a crystal clear answer and a not so clear answer depending on two scenarios:
Scenario 1: A ship stops on an obstacle, and on its next movement it's maneuver template is partly overlapping the obstacle the ship stopped on. This results in a second roll for potential damage, with no room for rules dispute.
Scenario 2: Here's where it's a bit more confusing. Let's say a ship stops on an obstacle, but only the "back end" of its base is on the obstacle. In the ship's movement next turn, its base will still be (partially) overlapping the obstacle but the maneuver template will not be. This is where it gets curious.
According to moving through obstacles:
"When a ship executes a maneuver in which either
the maneuver template or the ship’s base physically
overlaps an obstacle token, follow these steps:" (rulebook pg19)
So we need to check what it means to execute a maneuver:
"Execute Maneuver: Holding the template
firmly in place, grip the side walls of the base
and lift the ship off the play surface. Then place
the ship at the opposite end of the template,
sliding the rear guides of the ship into the
opposite end of the template." (rulebook page 7)
So, the question is, does the ship's base at the starting point count as part of the maneuver execution? Since the definition of executing a maneuver is picking up a ship and moving it to its new location, I suppose there's room to argue that perhaps the starting place of a ship's base is ignored (ie the execution of a maneuver only begins once the ship is lifted from the table). If this is the case, there wouldn't be another roll for damage if the maneuver template and stopping point of the second movement didn't overlap the obstacle.
BUT, both the picking up and placing down of a ship seem to be part of executing a maneuver, so I suspect that if a ship stops on an obstacle then its next movement will still require another roll for damage even if only the ship's base pre-moving overlaps the obstacle (but the man. template and ship base at the end of the move don't overlap any obstacle). Since the definition of executing a maneuver references both picking up and putting down the ship, I think that the ship's base-before-movement is included in maneuver execution, and is therefore relevant for determining obstacle overlap. So this is how I would rule it, based on what the rules say.