“Watcher in the Wings” is a unique side mission where you have to use neither your combat nor detective skills in Batman: Arkham City. You have to only spot a stalker who has been observing you from afar throughout the campaign. You need to confront him to solve his mystery.
Where to find the Watcher in Batman: Arkham City?
There are four different locations where you can spot the Watcher. The fifth location will only be revealed after you have solved the mystery of the Watcher in the Wings. You can meet him in any order based on where you are in the storyline because certain story missions need to be completed before he appears.
Park Row
You can spot the Watcher in the Wings after rescuing Catwoman in her first story mission of Batman: Arkham City. Make your way to the southern edge of the Solomon Wayne Courthouse rooftop, just above the main entrance, and look across to see your mysterious stalker on a Hotel rooftop in Park Row.
Confront him and Azrael will decree that he has been watching you (Batman) to see if you are ready. He will then vanish in a trail of smoke, leaving behind a symbol for you to scan. This will add a marker on your map and complete one part of the side mission.
Industrial District
The second location where you can spot the Watcher is at the top of the Ferris Wheel in the eastern corner of the Industrial District. Head to the base of the Ferris Wheel and use your Grapple Gun to reach Azrael. He will leave you another symbol to scan.
The Watcher will only appear at this location after you have finished the Steel Mill mission in the storyline of Batman: Arkham City. If Azrael is still not there, restart your game and head back to the Ferris Wheel.
The Bowery
The next location where you can find the Watcher in the Wings is the rooftop of the tallest building in the Bowery. You, however, do need to interrogate Quincy Sharp to make Azreal appear. If he still does not, restart your last checkpoint and try again.
This is the same area where you deal with the Penguin at the Museum during the main storyline. Hence, when you are done with the mission, head out and look northeast of the subway entrance to catch Azreal.
Amusement Mile
After completing the Mr. Freeze boss fight, head to the rooftop of the building west of the GCPD to find Azreal. Your Watcher in the Wings will be right next to the Gotham City Olympus building in Batman: Arkham City.
Do note that you need to rescue Vicky Vale to make your stalker appear in this location. If he does not, restart your game.
Solve the Watcher in the Wings puzzle
After you have scanned all four symbols, the markers on your map will line up to form a sigil. Use the Batcomputer to move/rotate the sigil around until all four points match the four locations where you found the Watcher in the Wings in Batman: Arkham City. This will reveal a new location for the final meeting with Azreal.
Head over to the southeastern corner of the church in the Amusement Mile to find a large symbol on the wall. Scan it to have your first, proper conversation with your stalker. Relax. This is not a boss fight.
Azreal will reveal his name and the order he works for. He will also foretell a great catastrophe that will soon befall Gotham City before vanishing into smoke, again.