Goofs

When robbing the Cambridge bank, the video tape at the front door of the bank shows the date 06/16/10. On the FBI report, the date of the bank robbery is 9/2011.

Across the street from the flower shop is a bar called "Fitzgerald's". Later, a shot of the flower shop at night shows the reflection of the same bar across the street, but the sign says "The Junction", the real name of the Southie bar where the shot was filmed.

When the FBI is talking about Doug's crew, Gem's mugshot on his booking form shows his height as 73", or 6'1". Further down on the booking form, Gem's height is listed as 5'9".

As Doug is beating up the men who vandalized Claire's car, the apartment door goes from closed to open, then back to closed.

The robbers' van changes direction during the armored truck robbery. It happens a few seconds after the robbers jump out, not enough time for the van to turn around, especially on a narrow one-way street.

When Krista Coughlin gets into an accident after visiting Doug McCray before the Fenway heist,the cop calls Agent Frawley and tells him she was a "DWI." In Massachusetts, the cop would have referred to it as an OUI, for "operating under the influence."

In the end credits, George Carroll's writing credit for the song "Run It" misspells his real name, George Carroll, as "Carrroll".

When McCray is calling into the Fenway Park cash room, he tells one of the counters his hometown is Quincy, pronounced "Quint-see." A Boston native would pronounce it "Quin-zee."

The patches worn by Boston police officers in the movie are different than those worn by actual BPD officers. A genuine BPD patch features an image of the BPD headquarters building and "A.D. 1630" along the bottom (the year Boston was founded). The patches worn in the movie feature an image of a church and "A.D. 1629" across the bottom.

Near the beginning during the night, two police cruisers drive by with their headlights off.

It's common for police to "roll dark" when going to a domestic disturbance.

When Doug is being interrogated by the FBI, where Doug is seated in the interrogation room changes from when he first enters the room, during the interrogation, and then back to his original seated position at the end.

During the armored car robbery getaway in the Dodge Caravan, burns and bullet holes can be seen in the headliner of van before they shoot at any cops. The burn marks come from the hot bullet casings during practice runs before filming.

When the FBI considers past robberies the characters might be linked to, a display board shows "Bank Boston" with a date of 2008. Bank Boston merged with Fleet Bank in 1999 to form Fleet Boston, which merged with Bank of America in 2004.

When Special Agent Frawley reviews Claire Keesey's case file, the report says the crime occurred in September 2011. It also states that Keesey was born on May 19, 1978, and is 30 years old. If the crime occurred in September 2011, this would make her character 33 years old.

When Doug MacRay is talking to his father on the phone through a pane of glass in prison, a camera shot that focuses on Doug shows a reflection of the elder MacRay with his mouth moving, although neither character is speaking at the time.

When Doug and Claire visit the assistant bank manager in hospital, he says "I just want to get back to work." In the reverse angle shot, his lips don't move.

While talking to Claire in the community garden, Doug's mouth does not move when he says "'Cause you'll f*cking..." in the reverse angle shot (then normal mouth movements "...hate the answers!").

When the ambulance hits the FBI Mobile Command Center, cables are visible along the street to pull the truck back.

During the chase after the armored car robbery, two separate sets of ramps, to let the vehicles drive over the cobblestone curbs without blowing out their tires, are visible. It's most obvious right after they enter the Jeep and drive onto the main road.

In the Extended Cut, after the first bank robbery, the assistant manager is said to be recovering at Beth Israel Deaconess Medical Center, a large Boston hospital. When Doug and Claire visit him, "City of Angels Medical Center" (a Los Angeles hospital) is written on the side of the building in the establishing shot.

When Doug flees to the Anderson RTC commuter rail station, the platform sign says "Trains to Florida". Trains that go through that station travel from Boston to Lowell (MBTA) and Boston to Maine (Amtrak).

The FBI suspects both Claire and Doug and yet they do not start surveillance straight away (they do say they cannot follow them 24/7 but this does not mean no surveillance at all); they would have busted them together at the terrace (like Jem easily did).

In the Extended Cut, Doug and Claire talk about Doug's parents twice; once while walking across a bridge during their first date, and the second time in a garden. The dialogue is nearly identical both times. The garden scene does not appear in the theatrical cut.

In the Extended Edition Blu-ray version, Frawley calls the bank and is told Claire quit her job Friday. In the next scene, Claire tells Doug "I quit my job today."

In the Extended Cut, when Doug and James are talking by the graveyard, Doug accidentally calls James "Jeremy". In the regular cut, this part of their conversation is removed; the longer conversation only appears in the Extended version of the movie.

Claire says "Years ago, he had lymphoma," with a British accent.

Doug does not get rid right away of Claire's driver's license; this could have been incriminating evidence had it been found on him or at his house.