Obtaining Spy achievements

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A Cut Above
A Cut Above
Kill a gun-wielding Spy with your knife.
Difficulty: Easy
How to obtain: An enemy Spy who is near friendly lines, retreating, or has recently respawned will likely have the Revolver equipped. Any of these opportunities gives you the chance to chase down and kill that player for the achievement.


Agent Provocateur
Agent Provocateur
Backstab your Steam Community friends 10 times.
Difficulty: Easy
How to obtain: Join a group of players that regularly play together. You do not have to backstab ten different friends, so it is possible to backstab a single friend multiple times.


Burn Notice
Burn Notice
Survive 30 seconds after being ignited while cloaked.
Difficulty: Very Easy
How to obtain: While cloaked, head to the front lines and look for an enemy Pyro. Bump into the Pyro's flames and then retreat to safety. Extinguish the flames with a Health kit and avoid entering combat until thirty seconds have elapsed.


Come in From the Cold
Come in From the Cold
Get a Revenge kill with a backstab.
Difficulty: Easy
How to obtain: You'll eventually be dominated by another player without trying. If you are having trouble getting revenge, you can be purposely dominated by a class you are strong against, such as the Sniper.


Constructus Interruptus
Constructus Interruptus
Kill an Engineer who is working on a sentry gun.
Difficulty: Easy
How to obtain: Look for an Engineer who is setting up or has built a Sentry Gun near a contested chokepoint. As your team makes a push through the area, backstab the distracted Engineer as he repairs the Sentry Gun.


Counter Espionage
Counter Espionage
Backstab a disguised Spy.
Difficulty: Easy
How to obtain: An enemy Spy that decloaks near your team is bound to already be disguised. Electro Sappers being placed on friendly Engineer buildings are sure signs that a disguised Spy is nearby. You can Spy-check by approaching the backs of teammates with the Knife equipped; if you automatically raise it as if to backstab someone, that "teammate" is actually an enemy Spy.


Deep Undercover
Deep Undercover
While using the Cloak and Dagger, kill the same enemy 3 times, all within the same area in a single life.
Difficulty: Medium-Hard
How to obtain: Camp in areas with high player traffic and use the Spy's ability to see player names to target a specific person. As long as you don't get killed, this achievement can be done over a prolonged period of time. Play conservatively; if you manage to backstab the same player twice, they are more likely to try and hunt you down. Due to specific anti-Spy gear, such as the Razorback or Jarate, even targeting a Sniper may not be an easy way to obtain this achievement.


Die Another Way
Die Another Way
Kill a Sniper after your backstab breaks his Razorback.
Difficulty: Medium
How to obtain: You will be shocked after your first backstab attempt, alerting the Sniper to your presence. After the Razorback is broken, either try to land another backstab or use your Revolver to finish the kill. Alternatively, you can use the Ambassador to headshot the Sniper before he can react. Using the Dead Ringer can also give the Sniper a false sense of security after "killing" you, allowing you to come back for an easy backstab.


Diplomacy
Diplomacy
Kill 50 enemies with the Ambassador.
Difficulty: Easy-Medium
How to obtain: Use good aim to land headshots on unwary enemies. You can use your cloak to prey on injured players as they retreat from battle.


Dr. Nooooo
Dr. Nooooo
Backstab a Medic that is ready to deploy an ÜberCharge.
Difficulty: Medium
How to obtain: When you see a Medic with an ÜberCharge ready, backstab him before it is deployed. You can use the Cloak and Dagger to stalk a Medic who is still building his ÜberCharge meter.


Fast Fingers
Fast Fingers
Backstab a Scout that is using the Back Scatter.
Difficulty: Easy-Medium
How to obtain: Identify a Scout on the other team who is using the Back Scatter and focus particularly on backstabbing him. He will be most distracted when trying to get into close range of an ally to shoot their back, so keep an eye on routes the Scout could take towards your team.


For Your Eyes Only
For Your Eyes Only
Provide an enemy with a freezecam shot of you flicking a cigarette onto their corpse.
Difficulty: Easy-Medium
How to obtain: After killing an enemy, stand on that player's corpse and taunt while holding the Disguise Kit. Should you do the Spy Crab taunt rather than flick a cigarette, the achievement will still be awarded.


FYI I am a Spy
FYI I am a Spy
Backstab a Medic who has healed you in the last 5 seconds.
Difficulty: Medium-Hard
How to obtain: Disguise yourself so that you best fit the current situation; if you are at the frontlines, disguise as perhaps a Soldier or Pyro. If you immediately head backwards after being healed, a competent Medic will instantly recognize you as a Spy. It may be easiest to perform this in the midst of a large firefight, where the Medic will have to pay more attention to the battle after healing you.


High Value Target
High Value Target
Backstab an enemy who is dominating 3 or more of your teammates.
Difficulty: Medium
How to obtain: Depending on the map and players, it may be hard to find someone who is dominating three or more of your teammates. Use the information on the scoreboard to track how many dominations each player has and target any appropriate enemies.


Identity Theft
Identity Theft
Backstab the enemy that you're currently disguised as.
Difficulty: Easy
How to obtain: The name of the player you are disguised as will appear on your HUD. Use this to seek out and backstab your victim. Disguising as an isolated Engineer or Sniper can allow you to more easily travel around without drawing suspicion. If wielding the Cloak and Dagger, you can continuously change your disguise until it corresponds with a nearby player.


Insurance Fraud
Insurance Fraud
Kill an enemy while you're being healed by an enemy Medic.
Difficulty: Medium
How to obtain: Once an enemy Medic starts to heal you, backstab the nearest enemy. This achievement is best done in the midst of a large firefight where the Medic will be paying more attention to the battle instead of you. You will automatically be healed by a Medic if you backstab their patient with Your Eternal Reward, allowing you to quickly go for another enemy.


Is It Safe?
Is It Safe?
Backstab 50 enemies who are capturing control points.
Difficulty: Medium
How to obtain: Some control points are quite confined, making it difficult to get within melee range of a Spy-checking group of players. Sparsely defended control points, such as those on Gravel Pit, make excellent areas to stalk. Players that huddle around the Payload cart make for easy targets.


Joint Operation
Joint Operation
Sap an enemy Sentry Gun within 3 seconds of a teammate sapping another.
Difficulty: Easy
How to obtain: When the enemy team has multiple Sentry Guns set up, coordinate with a fellow Spy to disable several of them at once.


May I Cut In?
May I Cut In?
Backstab an enemy and the Medic healing him within 10 seconds of each other.
Difficulty: Easy
How to obtain: Look for a Medic and his buddy as they head towards the front lines. Medic buddies tend to run more slowly, so it is preferable to stab the faster Medic first.


On Her Majesty’s Secret Surface
On Her Majesty’s Secret Surface
Start capping a capture point within a second of it becoming available.
Difficulty: Easy
How to obtain: Players tend not to pay attention to currently locked control points, so maneuver behind enemy lines and position yourself on the next control point in anticipation of your team capturing the preceding one. Using the Cloak and Dagger will allow you to hide indefinitely while waiting. Standard Control Point maps, such as Granary and Well, have control points that frequently change hands, and thus give you more opportunities to attempt this achievement. You only need to begin the capture process, not complete it.


Point Breaker
Point Breaker
Kill 15 enemies who are standing on a control point they own.
Difficulty: Medium
How to obtain: Players tend to Spy-check anyone approaching an active control point, so approach from an unexpected angle. Backstabbing enemies passing through a locked control point will also grant points towards this achievement.


Sap Auteur
Sap Auteur
Destroy 1000 Engineer buildings with sappers.
Difficulty: Easy
How to obtain: You will obtain this achievement after playing as the Spy for a decent amount of time. You will still get points towards this achievement via assists should a teammate destroy a building while it is being sapped. Only destruction via the default Sapper will count towards this achievement.


Sapsucker
Sapsucker
Sap an enemy building, then backstab the Engineer who built it within 5 seconds.
Difficulty: Easy
How to obtain: Use your cloaking or Disguise Kit to sneak behind a preoccupied Engineer. Sap a building, quickly switch to your Knife, and then backstab the Engineer to prevent your sapper from being removed. If an Engineer has left the building unattended, hide until they inevitably return to repair it. Players using the Wrangler tend to focus more on combat and can be easily distracted from their buildings.


Skullpluggery
Skullpluggery
Headshot 20 Snipers with the Ambassador.
Difficulty: Easy-Medium
How to obtain: Whenever you are in a position to backstab an enemy Sniper, use the Ambassador instead. Because an accurate Ambassador headshot only deals 102 damage (which scales down from a distance), it may be safer to target Snipers who are already injured or are away from the front lines.


Slash and Burn
Slash and Burn
Backstab an enemy, who then switches to Pyro before they respawn.
Difficulty: Easy-Medium
How to obtain: The procedure for this achievement is completely out of your hands. Continuously backstab enemies with the hope that one will become frustrated enough to switch to the Pyro.


Sleeper Agent
Sleeper Agent
Kill an enemy who triggered your feign death in the last 20 seconds.
Difficulty: Easy-Medium
How to obtain: To make your fake death more convincing, try allowing the enemy to damage you for a bit before pulling out the Dead Ringer.


Spies Like Us
Spies Like Us
While cloaked, bump into an enemy cloaked Spy.
Difficulty: Very Easy
How to obtain: This should happen incidentally as Spies tend to take routes that members from either team rarely traverse. You should eventually bump into an enemy Spy who is on the same path as you.


Spymaster
Spymaster
Backstab 1000 enemies.
Difficulty: Easy
How to obtain: You will naturally obtain this achievement after playing as the Spy for a decent amount of time.


The Man from P.U.N.C.T.U.R.E.
The Man from P.U.N.C.T.U.R.E.
Stab an enemy while fencing.
Difficulty: Very Hard
How to obtain: The Fencing Kill taunt is notably harder to perform than other taunt kills. In addition to being one of the longest and loudest taunts, you must also be undisguised and uncloaked. The first two strikes deal minimal damage and will easily alert enemies; use your ability to see enemy health to gauge whether your target is injured enough to be killed. To reduce the chances of being caught, perform the taunt from where you cannot be seen, such as around a corner or outside an enemy Teleporter Exit, allowing only the last strike to hit. This achievement cannot be obtained during Humiliation.


The Man with the Broken Guns
The Man with the Broken Guns
Backstab an Engineer, then sap 3 of his buildings within 10 seconds.
Difficulty: Easy-Medium
How to obtain: Find an Engineer with a building next to an active Teleporter. Backstab the Engineer and sap both the building and Teleporter. Another sapper will automatically be placed at the other end of the Teleporter, earning you this achievement. The buildings only need to be sapped, not destroyed.


The Melbourne Supremacy
The Melbourne Supremacy
Dominate a Sniper.
Difficulty: Easy-Medium
How to obtain: Specifically target an unaware enemy Sniper. If the player is carrying the Razorback, three point-blank Revolver shots or two rounds from the Ambassador (if the first is a close-range headshot) will do. If you are about to die, ensure that the Sniper does not receive an assist towards your demise. Hope that the player does not change classes before you manage a domination.


Triplecrossed
Triplecrossed
Backstab 3 Snipers in a single life.
Difficulty: Medium
How to obtain: This is most easily done on maps that favor Snipers, such as 2Fort, where multitudes of Snipers are sure to be found lined up and ready to be backstabbed. Note that you do not need to backstab all three Snipers within a short period of time, so retreating after the first or second backstab is a viable option.


Wetwork
Wetwork
Stab an enemy to death while under the influence of Jarate.
Difficulty: Medium
How to obtain: A Sniper who manages to hit you with Jarate or the Sydney Sleeper will already know you are there. Once hit, stay out of the Sniper's line of fire and attempt to backstab a different target who may not immediately be aware of your presence.


Who's Your Daddy?
Who's Your Daddy?
Headshot 3 Scouts with the Ambassador.
Difficulty: Medium-Hard
How to obtain: Scouts move quickly and are difficult to headshot. As when sniping, try to predict where the Scout will be when you fire. The Spy does not and cannot zoom in to get headshots, making close range encounters with Scouts slightly easier. Scouts in the midst of combat tend to be already injured, so the 102 damage an Ambassador headshot deals should suffice.


You Only Shiv Thrice
You Only Shiv Thrice
Backstab 3 enemies within 10 seconds.
Difficulty: Easy-Medium
How to obtain: Spies will frequently find themselves behind enemy lines with at least three nice big backs facing them. When this happens, attempt to backstab all of them.