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What is CTF Well?
In Team Fortress 2, CTF Well is a capture-the-flag map featuring two bases separated by a train track in the middle. Outside the bases are train cars, crates, bridges, two moats, and a train that passes by every few seconds. Inside each base is the intel room, the largest area of the map. Spies will enjoy moving around in the intel room because it has many good places to hide. If Spies become too much of a pest for the team, then send a Pyro to the intel room to take them out.
There are three significant areas in CTF Well some classes should have fun playing in. The focus here will be about going on the offensive side of the game.
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The waters of the two moats are a great place to hide, to get rid of any burns, and to easily take down poor combatants (everyone moves slower in the water). It's also a great spot for a Sentry Gun, something players won't suspect will be there. Engineers will usually build their Sentries in front of their base, near the train cars, near their spawning rooms, and inside the intel room.
In the water, the best spot to put a Sentry Gun is in the middle or above the large pipe. In the middle the Sentry Gun can detect any enemies swimming on the far left or right side of the moat. If Engineers stand near a Dispenser, they can stay in the water as long as they like.
Underwater the Engineer can sneak attack the enemies and create a shortcut. The quickest way to do this is by building everything on top of the large pipe (the one by the enemy base) in this order: Teleporter Exit, Dispenser, and Sentry Gun. Don't forget to put a Teleporter Entrance near your spawning room before you start building everything else.
Enemies coming through the pipe won't see the Sentry Gun above them and will easily get hit by it. It should take them awhile before the figure out where the Teleporter Exit is, so your teammates will have a hidden shortcut to get inside the enemy base.
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Demomen, Soldiers, Snipers, and Heavies can all go on top of the train cars and fair well attacking anyone from below. The Demoman has the sticky bombs to launch him up there while the Soldier can jump higher by firing a rocket near his feet. From there they can even jump on the higher platforms around them. Another alternative to get on top of the train cars is to jump on the crates stacked next to them.
Sentry Guns can also be built on top of the train cars. Just watch out for enemy Snipers on the second deck; they can easily spot the Engineer and his Sentry Gun.
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Second Floor Deck
This is a great hiding place for Snipers, Soldiers, and Spies (with the Ambassador) to launch their attacks. You should consider sneaking up to the second floor deck inside the enemy base. Now you will see more enemies moving in front of you from below. The convenient part about this spot is you're in a much safer position since most of the action is happening below. If anyone outside happens to spot you, stay behind the walls to avoid any hit.
You can really help out the team from here by taking out any enemy Engineers building their Sentries or Dispensers below or any Heavy/Medic teams moving up ahead. Just watch out for any enemy Snipers that may also be up there on the deck.