Basic Spy strategy
The Spy specializes in deception and excels at punishing mistakes made by the enemy team. Although he is fragile and possesses some of the weakest weapons in the game, he can backstab enemies and sap Engineer buildings. The Spy will almost always operate behind enemy lines. To aid in this, he can use Cloaking and disguises to move about undetected. The ability to see enemy names and health levels allows him to pick off weakened foes with his Revolver. Because of the threat he poses, enemies will frequently Spy-check their teammates. The Pyro's flames nullify both Cloaking and disguises, making him the most dangerous counter-class to the Spy. A good Spy will use both his Cloaking and Disguise Kit to avoid drawing enemy attention.
Primary Weapons
Revolver / Big Kill
Use the Revolver when your backstab fails or when you cannot safely approach a target. It is an extremely accurate weapon, so you can use it to pick off weakened enemies from a distance.
Ambassador
Use the Ambassador if you are confident about your aim. The ability to headshot lets you take out most classes in only a few shots and pairs well with your ability to see enemy health.
L'Etranger
L'Etranger converts firepower into potential fleeing power. It pairs well with the Cloak and Dagger or Dead Ringer, watches that have their recharge methods restricted. You can use it to refill your Cloak from a distance.
Enforcer
The Enforcer's increased damage output is useful if you have to fight your way out of enemy lines and makes you a greater threat in one-on-one duels. However, the increased time it takes to activate your Cloak makes it easier to be discovered once behind enemy lines. The Enforcer is best used alongside the Dead Ringer, which still instantly Cloaks you upon taking damage, however, the cloaking penalty can be easily countered by hiding behind a source of cover, such as around a corner, before fully cloaking, as long as you're not already in open combat.
Secondary Weapons
Electro Sapper
The Electro Sapper will instantly disable an Engineer's building and can only be removed by the Engineer or the Pyro's Homewrecker. You have an unlimited supply and can place them rapidly on any building within melee range. Typically, you'll first backstab an Engineer, then quickly sap any nearby buildings to prevent them from firing at you. Your weapons deal reduced damage to any building that has an Electro Sapper on it.
Melee Weapons
Knife/Saxxy
The Knife deals pitiful damage. Unless you can backstab an enemy, you're probably better off using your Revolver in fights, especially after you've been discovered. However, if only a little more damage is required to kill your target, the Knife makes a reliable finisher.
Your Eternal Reward
The inability to initially disguise will make you rely more on your Cloak ability to find good hiding places. Once you obtain a disguise, you are free to approach your enemies from behind. Do not rely on the "silent killer" aspect of the weapon; dead enemies will still be able to communicate using text or voice chat. If you're stuck with a slow disguise, you can Cloak at any time to move at normal walking speed.
Conniver's Kunai
The Conniver's Kunai's health reduction will make you very, very frail. Unless you are under the effects of its overheal, you can be killed by just one stray projectile. When using the Conniver's Kunai, play aggressively and try to land continuous backstabs to maintain your health. Using the Dead Ringer in conjunction with the Conniver's Kunai will allow you to quickly navigate behind enemy lines without dying to a random shot.
Big Earner
The Big Earner's health reduction does not make you as frail as the Conniver's Kunai but still allows you to instantly be killed by stronger weapons like the Soldier's Rocket Launcher. Play aggressively and get multiple kills to rapidly charge your Cloak for an easy escape. The Dead Ringer benefits greatly from quick recharging and will allow you to navigate behind enemy lines without dying to a random shot. The Cloak and Dagger also pairs best with this weapon, since you can not charge it from any other sources. As long as you can keep taking down targets, you can spend less time sitting and charging, and more time getting where you need to go.
PDA 1
Disguise Kit
The Disguise Kit is one of your major infiltration tools. Do not linger in front of enemies too long; you might be disguised, but you are still vulnerable to Spy-checking. Don't behave like a Spy; for example, reloading your Revolver while disguised will mimic your disguise's reload animation, allowing you to better blend into an enemy crowd. You can safely change your disguise while cloaked to throw off enemy suspicion. A disguise takes one second to become effective, so avoid the common mistake of approaching an enemy before the change is complete. Once you have successfully navigated behind enemy lines, it is easiest to backstab foes while they are distracted by your teammates.
PDA 2
Invisibility Watch / Enthusiast's Timepiece
Out of all your watches, the Invisibility Watch has the smallest margin of error but allows you to cover the furthest distance while invisible. Keep moving to decrease the chances of you being detected or cornered and grab metal pickups to keep your Cloak filled. While observant enemies may see the ammo box disappear, they probably won't be able to track you down.
Cloak and Dagger
The Cloak and Dagger is best used on maps with few metal pickups. You can use it to camp an area to pick off important targets, such as enemy Medics. Over the same amount of time, moving to a location slowly or in quick bursts will drain the same amount of Cloak. Continue to be mobile; enemies will be encouraged to Spy-check if you stay in the same area too long. Likewise, don't just use the Cloak and Dagger to stay out of harm's way; being alive does not necessarily mean being useful.
Dead Ringer
To make your feign death more convincing, consider letting the enemy damage you for a bit before taking out the Dead Ringer. Simply "dying" from fall damage is a sure sign that you're a Spy. While enemies will not see you if you bump into them, you are still vulnerable to revealing effects such as fire, bleeding, and Jarate. The reduced damage you take will aid in crossing firefights and finding safe hiding spots to decloak in. Know where metal pickups are so that you can quickly refill your Cloak for emergencies.
Item sets
The Saharan Spy
The Saharan Spy item set pairs best with the Dead Ringer. The set reduces the loud decloak volume significantly, making it easier to find suitable hiding places. Because your Cloak never shimmers when using the Dead Ringer, the increased Cloak blink is nullified.
The Man of Honor
The Man of Honor set is best used with the Dead Ringer; the instant cloaking time is not affected by the Enforcer's drawbacks while the damage reduction helps cover the Big Earner's health penalty. The Big Earner allows you to refill your Cloak very rapidly when on a killing spree, allowing you to use the Dead Ringer again and again.
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