Obtaining Spy achievements

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The BLU Spy


A Cut Above
A Cut Above
Kill a gun-wielding Spy with your knife.
Difficulty: Easy-Medium
How to obtain: If the opposing Spy just respawned or you are already inside the enemy base, he will likely have the Revolver equipped, so quickly backstab him. You could also try attacking an enemy Spy whose health is low, who will doubtless go for his Revolver, especially if you can ambush him first.


Agent Provocateur
Agent Provocateur
Backstab your Steam Community friends 10 times.
Difficulty: Easy-Medium
How to obtain: This will eventually happen. It is a lot easier if you are in a clan and/or you generally play against people on your friends list. You do not have to backstab ten different friends, so if you're playing against one friend, you can backstab him multiple times in one round to get this achievement faster.


Burn Notice
Burn Notice
Survive 30 seconds after being ignited while cloaked.
Difficulty: Very Easy
How to obtain: Easier to do while on defense. While cloaked, head to the front lines and look for an enemy Pyro attacking someone else. Bump into the flame, and quickly retreat to safety and grab a health kit or get the attention of a friendly Medic. After that, simply avoid going into combat until you get the achievement.


Come in From the Cold
Come in From the Cold
Get a Revenge kill with a backstab.
Difficulty: Easy
How to obtain: Chances are you will eventually get dominated without trying. When this happens, make an effort to get revenge by a backstab. Note that this may be harder to accomplish if you have been dominated by a Pyro or Scout. You can also get purposely dominated by an easy-to-backstab class, and then make an earnest attempt to kill your nemesis afterward.


Constructus Interruptus
Constructus Interruptus
Kill an Engineer who is working on a sentry gun.
Difficulty: Very Easy
How to obtain: Simply look for an Engineer who has built a Sentry Gun near a chokepoint that your team needs to pass, as they will likely be paying attention to their Sentry Gun rather than their surroundings. Then wait for your team to make a push, and stab the Engineer while he attempts to tank his gun. The Cloak and Dagger can help with this achievement, as you can wait patiently for the perfect moment to strike, though sitting near an enemy Dispenser also works. Beware, if he has built his Dispenser at his back, you will need to get on top of his Dispenser in order to reach his back. Another easy way to get this is to target Engineers who are just beginning to set up their guns or are in the midst of upgrading them. You can also attempt to stalk an Engineer who is carrying his Sentry to the front lines and backstab him once he begins setting up, as the Sentry requires several seconds to unpack before it is able to attack.


Counter Espionage
Counter Espionage
Backstab a disguised Spy.
Difficulty: Easy
How to obtain: Easier to do on defense, where enemy Spies will be more aggressive, and more likely to be careless. If you see an enemy Spy decloak, try to backstab him, or simply patrol behind your team using your knife on your teammates' backs. Alternatively, you can attempt to infiltrate the enemy offense and backstab an enemy Spy as he approaches your base, as they will most likely be disguised but not cloaked yet, and thus far easier to identify. Killing enemy Spies as they attempt to place Sappers on friendly buildings is another way, as they must stay disguised in order to avoid being killed by nearby Sentry Guns.


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: This achievement may take some time to get. If a player is backstabbed twice by the same person, they're likely to come at you with a flamethrower. Even targeting a Sniper might not be an easy way to get this achievement due to specific anti-spy gear they may be toting (Razorback, Jarate). You can attempt to get this by camping high-traffic areas and specifically targeting a specific person (such as a Heavy), then cloaking, running away, healing, and repeating. You do not have to do this in succession or even a limited amount of time. As long as you don't get killed, the achievement will count, so being careful pays off. After backstabbing your target, try to observe the area where you backstabbed them from a distance, as they will likely check around the immediate area for Spies after respawning. An ideal map to get this achievement on is on 2Fort, as it is relatively easy to escape and hide after one backstab, avoiding your target until they stop searching for you. Snipers tend to be very unwary of their immediate surroundings while on the battlements. Alternatively, try doing this while attacking on an Attack/Defend or Payload map, where the enemy will likely be staying close to their spawn, defending their final control or Payload point. Note that killing someone who has a Dead Ringer active counts as a kill, so 2 kills towards this achievement can be done per "real" life of the opposing Spy.


Die Another Way
Die Another Way
Kill a Sniper after your backstab breaks his Razorback.
Difficulty: Medium-Hard
How to obtain: This is going to depend on the skill of the Sniper. You are going to get shocked after the first backstab attempt, but with careful timing, you can pull this off. This may be considerably easier to do with the Ambassador, as you can land an easy Critical hit or two on them as long as they're not paying attention. You can attempt to use a Dead Ringer and goad them into attacking you after breaking their Razorback, and then decloak a safe distance away and come back for them.


Diplomacy
Diplomacy
Kill 50 enemies with the Ambassador.
Difficulty: Medium
How to obtain: Not necessarily difficult, but may take some time since the Ambassador does less damage than the standard Revolver. You can attempt to get this achievement by headshotting unwary Snipers with your Ambassador rather than backstabbing them, though in all cases it will take two or more shots unless they were wounded previously. Be wary of Snipers using the Croc-o-Style Kit, as they cannot be killed with headshots.


Dr. Nooooo
Dr. Nooooo
Backstab a Medic that is ready to deploy an ÜberCharge.
Difficulty: Medium
How to obtain: Just sit back and wait until you see a Medic with an ÜberCharge ready, then try to backstab him before he deploys it. This works well on CP maps when the enemy team is organizing for a push. Just be sure not to act suspiciously as you wait, or use the Cloak and Dagger to stay hidden. However, be sure to uncloak a bit before attempting the backstab, so that you can immediately execute it upon reaching your target.


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: Just backstab an enemy who is away from his team, pull out your cigarette case and taunt while standing on his corpse. Your victim must appear in the freezecam shot, so if you backstab or headshot your target be sure that you do it towards a wall or corner, or that your attack results in a special death animation. This achievement is also awarded if you do the Spy Crab taunt.


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: This one depends largely on the skill of the Medic. As soon as a decent Medic sees you heading backwards after being healed, he's taking his saw out. You can slow down slightly and try to perform a sidestab. Alternatively, you can try to disguise as someone with low health, and call for a Medic who is healing a high-priority class (like a Heavy) close to a battle area; if you're lucky, they will top you up to full health and then turn their attention back to their buddy, allowing you to backstab him within the 5 seconds. Note, however, that if the Medic is smart and does not see you emerging from the battle area, calling may simply result in him Spy-checking you, so be careful and use your judgement.

If the Medic in question realizes that you are a Spy, you can attempt to use this to your advantage. Medics generally try to chase Spies away, since they are aware you will try to kill him or his patients again later. Simply approach the Medic with low health, once he realizes that you are a Spy try to lure him away from his teammates and backstab him. This is exceptionally easier if you can perform the stairstab tactic.

Note that this achievement is considerably easier when using Your Eternal Reward; managing to backstab a Medic's patient without him noticing will prevent any suspicion from falling on you (as long as you act naturally), buying you precious time to prepare your attack.


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 player (as well as their class), it may be hard to find a player who is dominating three or more other players on a map where you have more than one route to get behind enemy lines. If it's a Pyro then don't bother, but if it's a Soldier, Heavy, or Sniper, then this can be done quite easily. Furthermore, because the number of dominations are shown in the scoreboard, you can simply disguise and hide amongst the enemy team until you see that player, then backstab him.


Identity Theft
Identity Theft
Backstab the enemy that you're currently disguised as.
Difficulty: Easy
How to obtain: Disguise yourself as an Engineer or a Sniper - easy Spy prey that isn't too fast. Your disguise name will show on your HUD, so after you equip your disguise, seek out that person and backstab him. Alternatively, if you have the Cloak and Dagger, you can get behind enemy lines, find a lone Sniper or Engineer (or even Demoman), change your disguise until you disguise as that player, decloak and backstab him. Be sure not to be spotted by that player though, as they will immediately realize that you are a Spy and may announce it to the rest of their team.


Insurance Fraud
Insurance Fraud
Kill an enemy while you're being healed by an enemy Medic.
Difficulty: Medium
How to obtain: Just get the attention of a Medic and when he starts to heal you, go and stab the nearest person. It may be easier to pull this off while disguised as a Heavy, Soldier, Demoman, or Pyro, as those are classes that generally have Medics attached to them. However, beware that disguising yourself as a Heavy or Soldier also makes it harder to get behind a target to backstab unless they are standing still. Getting the attention of a Medic close to a battle area may also help, and infiltrating an enemy group about to make a push may also net you this achievement inadvertently. If possible, try to disguise as a player with low health, so that the Medic will spend more time trying to heal you. Spies using Your Eternal Reward that backstab a medic's patient will automatically be healed by the medic. Kill another enemy quickly before the medic can realize what's happened.


Is It Safe?
Is It Safe?
Backstab 50 enemies who are capturing control points.
Difficulty: Medium
How to obtain: This is a grind achievement, but a more difficult one. Some control points are very confined, making it difficult to walk in without bumping into somebody. Also, more skilled players tend to Spy check anyone who comes in. This achievement is a lot easier to get points for on CPs that are in a more open area. This may be easier to accomplish by camping a sparsely defended control point (such as in Gravel Pit) with the Cloak and Dagger, and then eliminating anyone who approaches to capture it. It can, however, be considerably easier to perform on Payload maps, when the enemy team huddles around the cart and shoots at your teammates, not paying attention to their backs. Just remember to check for any enemies that are watching the rear of the team to avoid being discovered too early.


Joint Operation
Joint Operation
Sap an enemy Sentry Gun within 3 seconds of a teammate sapping another.
Difficulty: Easy
How to obtain: This is easier to accomplish if the enemy team has a large Sentry nest defending a point. Simply keep an eye on the Sentry nest until a friendly Spy appears, then decloak and go to town with your Sappers.


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: Just look for a Medic and his patient as they head towards the front lines, and approach from behind. Stab the Medic first, then his buddy; if you stab the buddy first, the Medic will quickly retreat or attack, denying you the chance to kill him as well. This is easiest to do with a slower class like the Heavy or Soldier, as the Medic will have to slow down to stay behind his buddy, and those classes are generally focused on what's in front of them. Medics that are using the Kritzkrieg are also easy targets, as they tend to let their guard down upon deploying their ÜberCharge, allowing you to quickly stab him and his buddy.


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: Enemies tend not to pay attention to CPs that are currently locked, so it becomes a simple task of getting behind enemy lines and to the next CP while your team fights for the current one. This is more easily accomplished with the Cloak and Dagger so long as you're careful as you move toward their control point. Dustbowl and the final point in Well are good choices. Under the right circumstances, Steel will also offer many opportunities for this, and the final point on Gravel Pit works as well. Beware that some players will deliberately Spy-check their next CP in order to avoid a Spy cap, so waiting a fair distance away from the point is wise, as long as you can get onto it and remove your disguise before your team captures the current CP.


Point Breaker
Point Breaker
Kill 15 enemies who are standing on a control point they own.
Difficulty: Medium
How to obtain: Just as in "Is It Safe?" players tend to Spy check anyone approaching an active CP. This achievement may be best completed by attacking Engineers setting up on active CPs to defend them, or playing on defense and attacking people passing through a CP that they have already captured, such as Dustbowl stage 1.


Sap Auteur
Sap Auteur
Destroy 1000 Engineer buildings with sappers.
Difficulty: Easy
How to obtain: Will happen over time. The best way to get this achievement is to kill Engineers before sapping their buildings, as Teleporter Entrances can be saved from the other side, though you can avoid this by repeatedly sapping the Exit as they attempt to knock your Sappers off. If you can get to the enemy base undetected, then sapping the Entrances and telefraging the Engineer will make this significantly easier.


Sapsucker
Sapsucker
Sap an enemy building, then backstab the Engineer who built it within 5 seconds.
Difficulty: Easy
How to obtain: Simply cloak your way behind the Engineer while he's focused on a building, uncloak and sap it, then quick-switch to your knife and backstab the Engineer. Alternatively, find a lone Engineer, sap the building while he is away, Cloak and hide somewhere on an interception path, and then uncloak and backstab him as he passes by to knock off your Electro Sapper. If you can get behind an Engineer who is using the Wrangler, you can simply backstab him and then sap his Sentry Gun at your leisure, since the Sentry will shut down for three seconds after you kill him.


Skullpluggery
Skullpluggery
While using the Ambassador, kill 20 Snipers with a headshot.
Difficulty: Easy-Medium
How to obtain: Whenever you get behind a Sniper and are in a position to backstab him, simply use your Ambassador instead. Remember that the Ambassador only Crits while fully accurate, and only deals 102 damage with a headshot, so you may be forced to deliver a second shot; because of this, it is usually safer to shoot the Sniper after he has been hit a few times. This is somewhat easier to do against Snipers carrying the default Sniper Rifle, as the Huntsman gives them a wider field of view and may allow them to counterattack very quickly. A helpful trick is to take your shot when the Sniper stops momentarily to deliver his own shot. Remember to check to see if the Sniper has Darwin's Danger Shield or the Croc-o-Style Kit equipped, as the shield gives him an additional 25 HP and he cannot be killed with headshots if he is using the entire item set.


Slash and Burn
Slash and Burn
Backstab an enemy, who then switches to Pyro before they respawn.
Difficulty: Easy-Medium
How to obtain: This achievement isn't simple as the procedure is out of your hands. After killing someone, it's up to your victim whether or not they decide to switch classes. You can attempt this achievement by dominating a player through backstabbing them repeatedly, and hoping that they become frustrated enough to switch classes. It also has a higher chance of happening if the Spies on your team are severely hampering the efforts of the opposing team, the opposing team has few to no Pyros, or said Pyros are doing a poor job of Spy-checking. The more enemies you backstab, the better the odds that one of them will switch classes.


Sleeper Agent
Sleeper Agent
Kill an enemy who triggered your feign death in the last 20 seconds.
Difficulty: Easy-Medium
How to obtain: Most enemies will not be expecting you to backstab them after they believe you're dead. If it fails and/or the enemy starts getting suspicious, try fighting him first until he starts to take away some of your HP, then quickly pull out the Dead Ringer before he gets the next hit in, and decloak when it's safe and seek out your target. Note, however, that the Dead Ringer makes a very distinct sound when uncloaking, so you may wish to uncloak farther away and then finding your target using the remaining time. You may also try equipping the Saharan Spy item set, which reduces the volume of the decloak sound.


Spies Like Us
Spies Like Us
While cloaked, bump into an enemy cloaked Spy.
Difficulty: Very Easy
How to obtain: This should happen incidentally. Explore while cloaked, especially in tight corridors roughly halfway between your two team's spawn points or side paths that neither team is traversing often. You should eventually bump into a Spy who is doing the same.


Spymaster
Spymaster
Backstab 1000 enemies.
Difficulty: Easy
How to obtain: Should happen over time. This achievement will come faster if you backstab people in groups, such as when they're huddled around the Payload cart or are getting ready to make a push.


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: This achievement is done by using the Spy's taunt with the knife while undisguised and uncloaked. While it can be done on unwary Snipers, the taunt is not instant kill on the first attack, but rather does two Fencing attacks before the lethal final strike, which can easily alert your target if your voice does not. You can try getting this at gates at the beginning of the round if you're on defense, but it must be timed properly. Note that if your target has low HP, your first two swipes may be enough to kill them. This also works against an enemy Spy using the Dead Ringer.

It is important to remember that you must be undisguised in order to perform this taunt, so don't do it in the presence of Sentry Guns. The Cloak and Dagger helps with this achievement significantly, allowing you to choose the proper moment to strike, but remember to take your disguise off beforehand (simply change your disguise to a friendly Spy).

Targeting lone enemy Heavies who are eating a Sandvich or Dalokohs Bar is also a good way to get this achievement, as they will usually back into a corner in order to eat, allowing you to box them in; you must time your decloak and taunt well though, preferably right after they begin eating. If done right, even if they manage to take out another weapon, they will not be able to kill you before your final strike unless they land a Critical punch on you. This will require some excellent stalking skills though, as most Heavies will refuse to eat if they suspect nearby enemies.


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: Simply find an Engineer with a building next to an active Teleporter, then backstab him and sap the building and the teleporter. You will automatically place another Sapper at the other end of the Teleporter. It is not necessary to destroy the buildings with your Sappers, simply for Sappers to be placed on three buildings belonging to the Engineer that you backstabbed.


The Melbourne Supremacy
The Melbourne Supremacy
Dominate a Sniper.
Difficulty: Easy-Medium
How to obtain: Identify an enemy Sniper who isn't very good, and specifically target him for backstabs, even if his team is sure to kill you afterwards; if he is carrying a Razorback, three point-blank Revolver shots or two rounds from the Ambassador (if the first is a headshot) will do. As long as he doesn't kill you, it won't matter if you survive after killing him. Repeat until he is dominated, and hope that he does not switch to another class before then.


Triplecrossed
Triplecrossed
Backstab 3 Snipers in a single life.
Difficulty: Medium
How to obtain: This is most easily done on the enemy battlements in 2Fort, preferably on a server with a large amount of people (over 24) where multitudes of Snipers are sure to be found, lined up, ready to be backstabbed. Note that you do not need to backstab all three within a short period of time, simply don't die until you've done backstabs on three Snipers (or backstab two Snipers and do a suicide stab on a third one), so retreating after the first or second is an option. Be wary of Snipers carrying Razorbacks, however, as you will be left vulnerable upon breaking a Razorback. If you're worried about the Snipers' teammates killing you before you can escape, have the Dead Ringer equipped. The Cloak and Dagger also helps, as you can camp a frequent Sniper area and make multiple kills, though retreating temporarily after the first kill or so is advised so that you aren't discovered.


Wetwork
Wetwork
Stab an enemy to death while under the influence of Jarate.
Difficulty: Medium
How to obtain: Because Jarate nullifies your Cloak, this may be a hard achievement to get because the Sniper who threw it will almost certainly charge at you with his melee weapon, which outdamages your Knife in melee fights, even more so while you have been Jarate'd. Your best option is to attempt to backstab a different target who may not be immediately 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 hard to headshot if you do not have good aim. Unless they are standing still (e.g. trying to hit a target with their Sandman, attempting to kill someone with their taunt, or are sitting near a Dispenser), this one is largely luck. On the flip side, you may occasionally get a lucky shot if being chased, and due to their low HP a headshot will usually kill Scouts if they are not at full health, especially those carrying the Sandman. Don't bother against Scouts equipped with the Special Delivery item set though, as they have 150 HP and cannot be killed from full health with a headshot.


You Only Shiv Thrice
You Only Shiv Thrice
Backstab 3 enemies within 10 seconds.
Difficulty: Easy-Medium
How to obtain: Good Spies will frequently find themselves behind enemy lines with at least three nice big backs facing them. When this happens, go for it, sooner or later you will get the achievement. This works well on Payload maps if you are defending and your team's defenses have been destroyed, since players will generally be watching the direction that the cart is moving in when no enemies are around, as well as bunch up together close to the cart; just be sure to keep an eye out for players that are watching the back of the cart. Getting behind a group of enemies as they attempt a push will also often leave enemies inattentive to your presence. Snipers also tend to congregate in groups at certain areas on various maps, so if there are two Snipers in close proximity to each other, try to get the Snipers and then a third target in front of them. Getting a Medic, his buddy, and then one more in front of them in quick succession also works, as long as you are confident that their teammates can't kill you before then.