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 across a pane of glass in prison, a camera shot that focuses on Doug shows a reflection of the elder MacRay with his mouth clearly moving, although neither character is speaking at the time.
In the Extended Cut, Doug and Claire talk about Doug's parents twice; once in a restaurant during the 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.
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.
At the flower shop, a bar across the street is called "Fitzgerald's." Later in the movie, 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 scene was filmed.
At the beginning of the Fenway robbery Doug and James are walking into the park dressed as Boston cops. Doug's amount of stubble grows from the time he first enters the part until seconds later when he is opening the security panel. At that point he has much heavier stubble.
While chasing the minivan through winding back streets, a point-of-view shot looking forward during a tight right turn shows headlight beams sweeping across a facing wall, yet no vehicle in the chase has its headlights on.
During the chase scene 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 clearly 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).
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."
During the armored car robbery getaway in the Dodge Caravan, you can already see burns / bullet holes in the headliner of van before they even shoot at any cops. Burn marks come from the hot bullet casings during practice runs before filming.
At the end of the movie, when Coughlin is shooting at the SWAT officers in the garage as they approach from under the stands, he shoots an AK-47 style weapon with a folded stock. Just after Gloansy is shot in the bullet proof vest, Coughlin starts shooting with a AR-15 style weapon (folded stock). The camera pans onto the SWAT officers. When it pans back to Coughlin, he is again shooting the AK-47.
The bag Doug leaves for Claire in her garden contains money, a note, and a tangerine, hinting that he has gone to Tangerine, Florida, his missing mother's hometown. Doug's last scene of shows him in a stilt house on a coastal waterway. In real life, Tangerine Florida is a rural community in the middle of the state, far from the kind of waterway shown. As a fugitive, Doug is likely to lie about his true whereabouts in case the message was intercepted.