- Continuity: When Billy visits Madolyn active window of Microsoft Anti Spyware on her monitor disappears and appears in different shots.
- Continuity: Costello's signature on the condolence card on Mrs. Costigan's coffin clearly changes appearance between the two successive shots.
- Anachronisms: The sign in the window of the convenience store at the beginning of the film advertises The Boston Phoenix as a free paper. At the time being depicted "some years ago" the Phoenix cost $.35-.50 (depending on the actual year).
- Factual errors: The rank of "staff sergeant" does not exist in the Massachusetts State Police.
- Factual errors: Sullivan says that the highest decoration the Massachusetts State Police has is the Medal of Merit. It is actually the George Hanna Award.
- Incorrectly regarded as goofs: When Billy's phone goes off in the porn theater, it is on vibrate. However, in the alley when he is following Colin, it rings when he receives a text. The event is described in the script by William Monahan: "His phone has fucked up, as they do."
- Factual errors: When Colin is playing Rugby near the start of the film he is playing the position of flanker, but he is wearing the no. 10 shirt, which is the position of fly half.
- Continuity: When the truck is leaving the scene at 344 Washington, the left back window is shot out twice.
- Continuity: When Sullivan enters the surveillance room monitoring the microprocessor transaction between Costello and the Chinese, Barrigan and Brown are with him. In a following shot, however, Brown can be seen sitting at the far left of a table watching camera monitors with his coat off. In the next scene, he is standing next to Sullivan again and his coat is back on.
- Continuity: When Bill, Costello, and Mr. French are heading towards the cocaine warehouse in Gloucester, shots inside the car show them crossing the Zakim bridge Northbound. Shots outside the car show them heading towards the bridge Southbound.
- Continuity: When Queenan and Dignam confront Costello it's just the three of them standing there talking. But when Costello says "I've got a date with some angels." The camera goes back to Queenan and you see a fourth person standing there (the FBI guy) whom you've never seen before in the shot.
- Incorrectly regarded as goofs: The microprocessors sold to the Chinese government agents are simple 8/16bit MCUs manufactured by STMicroelectronics. They have 6 KBytes RAM and 128 KBytes Flash ROM, and are sold at every electronics store. You might get a rocket in the air with that kind of CPU, but not very accurately. However, someone mentions later that the Chinese got busted with a set of "lamp sockets", and asks what Costello did with the real microprocessors.
- Errors in geography: When Queenan gets on the train at Park Street station on his way to meet Costigan, Costigan calls him and tells him to get off at the next stop; Queenan responds, confirming that the next stop is South Station. The stop after Park Street is Downtown Crossing, not South Station.
- Errors in geography: As Queenan leaves the South Station T stop to walk to the South Boston warehouse where he is to meet Costigan, he is walking north away from South Station. However, South Boston can be seen behind South Station, and is in the completely opposite direction.
- Continuity: As Costello walks out of the room where he was hitting Costigan's broken arm with a shoe, you see Costigan fall to the floor behind him. However, in the subsequent brief view from above, it shows Costigan falling to the floor again.
- Revealing mistakes: When Costello is hitting Costigan's arm with his shoe, he is clearly hitting the table area in front of his arm.
- Continuity: When Sullivan pulls up Costigan's record in the computer, his date of birth is initially listed as 11/7/1984 but then is shown as 11/7/1980 the second time he views it.
- Continuity: When the cops are set up to conduct surveillance on the microprocessor deal, the sweat stains on Ellerby's shirt change back and forth.
- Continuity: When Billy is talking with Madolyn for the first time in her office, the position of the tissue sticking out of the top of the tissue box on Madolyn's desk changes a few times.
- Boom mic visible: At the top of the frame during a wide shot of the police boardroom, a boom mike can be seen.
- Audio/visual unsynchronized: While Gwen is talking on the phone, the word "hell" is obviously dubbed over the initial word "fuck."
- Continuity: In one scene, Queenan hands Costigan a glass of ice water, which disappears and reappears between shots.
- Continuity: The taped recording of Costello and Sullivan that Madolyn listens to is from their conversation in the porn theater. However Costello's lines are different on the tape than they were in the theater. One example: While in the theater he says "It won't be me who suffers for it". Whereas on the tape you hear him say "It won't be me who pays for it".
- Continuity: When Costigan and Costello are in the diner with the priests and the nun, Costigan's necklace switches from under his shirt to in front of his shirt and then returns to back under his shirt for the rest of the scene.
- Continuity: When Sullivan uses Queenan's phone, the close-up shows the blood transferring from his finger to the left side of the talk button. The wide shot shows the blood on the right side.
- Errors in geography: When Costigan and Brown are training at the Mass. State Police Academy, the Throgs Neck Bridge, which connects Queens and the Bronx, is clearly visible. The actual Mass. State Police Academy is in New Braintree, Massachusetts, a small town near Worcester, with no large suspension bridges nearby.
- Factual errors: Early in the film when Sullivan is switching Sim cards in the phone booth, he's using a sprint RL7400 cell phone, which doesn't use Sim cards. The Sim card is also placed in the phone with the contact side facing up.
- Continuity: In the beginning when Frank executes a kneeling man and woman, the woman falls on the back of the man. The next scene shows her clearly beside him, then the next shot, she's back on the man's back.
- Anachronisms: The Boston Phoenix honor box outside the shop in the opening scene supposedly taken "some years ago" uses a logo that was introduced in 2005. The honor box is the same in subsequent present-day shots.
- Continuity: After Costello stops hitting Costigan's broken arm with a shoe, the arm is naked since all bandage and plaster is gone. Yet, in the subsequent brief view from above of Costigan falling to the ground the arm is still covered in white.
- Factual errors: At the early police officers briefing on the Chinese threats of getting the chips for their long distance rockets, the missiles appeared on the screen were just Russian SAMs anti-aircrafts.
- Anachronisms: When Frank picks up a Bic lighter at the luncheonette counter after talking to young Collin, you can see the "BIC" in yellow on the plastic part of the lighter. Bic didn't mark their lighters on the plastic until a few years ago.
- Factual errors: The processors in the movie are supposed to be made by a fictitious company called MASS Processor. However, the processors that are shown, clearly have the logo of the Italian chip maker giant ST Microelectronics. This goof is corrected in the DVD release.
- Anachronisms: Sullivan and Costello meet in an adult movie theater in Boston's Chinatown. However, an earlier reference to the Patriot Act places this movie no earlier than 2001. By then, the porno houses of Boston's "Combat Zone" were nothing but a memory.
- Continuity: When Costigan is meeting with Queenan and Dignam under the bridge, Dignam's hair is messed up, but from behind his hair is perfectly straight.
- Continuity: When Colin calls Costigan for the first time he smudges blood across the call button. In the next shot, the smudge is all but gone.
- Continuity: When we see Frank Costello from the back as he address young Colin in the auto shop, he has a cigarette in his mouth. In the next shot of him from the front, his cigarette is gone.
- Continuity: When Billy is in a bar, meeting Mr French for the first time, he walks near a payphone after punching a guy at the bar and pulls his jacket down. In the next shot, his jacket is back on again.
- Errors in geography: On the envelope Madolyn receives, Colin's address is shown as 20 Pickering in Boston. Pickering Ave. is in Roxbury, nowhere near Beacon Hill. The ZIP code shown is 02459, which is Newton Centre. In the DVD version, the ZIP code is 02149, which is Everett. Billy's return address is on Conant St. in Boston, but Conant St. is in Revere.
- Continuity: Costigan and French get into the maroon Buick Roadmaster, where Costello is waiting. When it shows Costigan open the flip-phone, the dashboard shown in the background is that of a newer Mercedes with a black interior.
- Factual errors: When Costigan is taking Oxycontin, the prescription label doesn't tell the strength and then shows the tablet as medium sized green and oval shaped. Oxycontin is a brand name and the only shape is small round of various colors (either white, blue, orange, or dark green depending on strength).
- Anachronisms: When Costello enters the convenience store in the beginning of the movie, The HALLS cough drops, located on the counter, are advertising a modern logo and would not be available when Colin was a boy.
- Continuity: In the scene where Costigan is talking to his uncle while his mother is dying in the hospital, there is clearly a fire extinguisher on the wall in the hospital hallway. However, after the scene cuts from Costigan to the uncle and back to Costigan, the fire extinguisher is gone but the hook is still visible.
- Errors made by characters (possibly deliberate errors by the filmmakers): UMASS/Boston is mentioned as being in South Boston. It's very close to South Boston, but it's actually in Columbia Point, Dorchester.
- Continuity: In the scene at the bar where Costigan and Costello's men are writing down their social security and account numbers for Costello, Costigan corrects Fitzy's spelling of 'Citizens,' and the open end of the envelope is facing to their right. When Fitzy picks up the envelope, however, it switches so that the open end is facing left, then right, then left again in subsequent shots.
- Continuity: When Costello gives Costigan money in the bar to have his arm checked out, he counts out three bills from the wad he's holding in his left hand and drops it on the pool table. In the next frame, the money has shifted to his right hand and there's no money on the table.
- Continuity: When Costello and Costigan are sitting down at the table in the restaurant discussing who the rat is, a handgun falls to the floor and Costello picks it up and points it at Costigan's face. As he does so, you can hear him manually thumb cock the hammer but when the camera angle changes the hammer is not cocked back anymore.
- Factual errors: As Sullivan investigates the site where the bodies of the Providence thugs were found, a police cruiser has "Lynne Police" stenciled on its side. The city of Lynn is not spelled with an "e".
- Errors in geography: The building addressed "344 Washington" in the movie is clearly in the Fort Point neighborhood, just off of Congress street near the Courthouse T stop, looking North West toward Atlantic Avenue/Financial District. However, there is no Washington St. in Fort Point
- Continuity: When Frank is in the diner in the beginning with young Colin, the package of lighters, the gum, the Halls candies, and the mints are rearranged each time the shot changes.
>>> WARNING: Here Be Spoilers <<<
Goofs below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- Revealing mistakes: SPOILER: The counterfeit State Police patches on the uniforms and logos and computer desktops are completely different from the authentic ones on the documentation in the evidence box for Queenan's murder and on the cruisers deployed for the arrest.
- Crew or equipment visible: SPOILER: When Costigan attempts to arrest Sullivan on the roof, some rigging appears in the sky.
- Continuity: SPOILER: When Frank is running away during the shootout, he gets shot on the left side of his body, and blood hits the wall. In the next shot, you can clearly see him running and no blood nor bullet holes in his shirt or jacket. When he sees Colin, he is taking off his jacket and his bullet wound has switched to the right side of his body.
- Crew or equipment visible: SPOILER: After Queenan is thrown from the roof, we see Costigan's POV shot. DiCaprio (who plays Costigan) moves his head only slightly to the right, we see the dolly track, if only briefly.
- Revealing mistakes: SPOILER: After Costigan is shot and killed, and his gun is kicked from his hands, if one listens very, very closely, one can hear the sound of a camera shutter firing. (This indicates that a publicity photo was being taken while the scene was being filmed).
- Revealing mistakes: SPOILER: When Costigan is in the elevator after he arrested and handcuffed Sullivan, Costigan slams against the wall with Sullivan. Sullivan's left hand is supposed to be handcuffed behind his back, but he puts out his hand to catch himself as he hits the wall.
- Crew or equipment visible: SPOILER: As Mr. French is backing up the car, and just before he gets shot, if you slow-mo the movie, you'll see that he has no beard. The driver is clearly a stuntman.
- Revealing mistakes: SPOILER: When Colin shoots Frank in the chest, killing him, the device used for mimicking a bullet wound is clearly visible under Franks gray "Irish" t-shirt.
- Continuity: SPOILER: When Costigan is discovering the envelope on Colin's desk, the markings on the envelope change at least twice in between shots.
- Continuity: SPOILER: Between the discovery by Costigan of the envelope on Colin's desk, and the return of Colin in the room, the arrangement of the various piles of documents on the desk have changed.
- Revealing mistakes: SPOILER: In the last scene, when Colin is shot and falling, you can see the stub of the tube used to splatter the blood.
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