So since the Watcher is engaged with both players in the Road Darkens is he dealt 2 shadow cards when he attacks? One for each player?

Yes. Attack each player follow particular rules, quite close to "additional attack".

So you deal a shadow card for the first player attack. Then, when you resolve attack on the second player you must discard the old shadow card on this ennemy and dealt it a new shadow card. And the same occur for any remaining players.

If you are playing in chronological order keep those rules in mind. I'm pretty sure you will need them again pretty soon

Great thanks. Well we have to play it over again because we didn't know the password. 😁

Another question regarding the Watcher. Does he put damage on the active location since he is engage with all players?

2 hours ago, ScottGilbert25 said:

Another question regarding the Watcher. Does he put damage on the active location since he is engage with all players?

No, because it has not actually engaged the players (so Mablung would not activate and so forth), even though is considered to be engaged (so effects like Heir of Valandil would count it). That Forced effect on Stage 4 of the Quest is activated basically only when an enemy is moved from the staging area to the play area of a player due to an engagement (whether is done by the players, by an engagement check or a card effect)