Does a unit that gets a bonus from attacking alone lose that bonus if Cloud City Wing Guard strikes using his ability (he can strike in an engagement even if he is not declared as an attacker)? Part of me wants to says yes since he was not declared as an attacker, but on the other hand he is attacking with the lone unit, albeit outside the engagement.

Also if striking outside the engagement would he be considered to be attacking alone?

A unit is attacking alone if and only if:

- It is currently participating in an engagement as an attacker

- There are no other units participating in the engagement as an attacker

Cloud City Wing Guard has an ability that allows it to strike even if not a participating unit, so it would not prevent another unit from attacking alone. However, the Cloud City Wing Guard can never be considered attacking alone if striking from outside the engagement because it is not an attacker.