Bentley: Any problems with that guy?
Sly: Said he wanted to be buried in his mom's pasta sauce.
Bentley: Yeah... that's, uh, that's strange.
― After a conversation with a guard[src]
Sly and Bentley need to steal the blueprints to the tar-pumping station so that they can find a way to stop Octavio from using it.
The blueprints to the tar-pumping station were hidden in a painting in each of Octavio's allegedly legit coffee houses. Bentley explained to Sly that since they destroyed Octavio's tar-pumping Ferris wheel, he went all out on security, having each of his guards checking up on each other. Therefore, to avoid raising any suspicion, this job required a unique approach. Sly had to don a Venice disguise and pretend to take the shift of each guard at the front doors of each coffee house, so that Bentley could head inside and swipe the blueprints. Each guard was going to ask Sly for a password, so Bentley would relay the hacked password to Sly, who had to quickly answer correctly to avoid detection.
While standing on top of a building above the first coffee house, Sly put on the disguise and relieved the guard at the door. Once the guard left, Bentley headed inside and found the art decryption lock. Bentley cracked the code and snagged the first blueprint.
Sly and Bentley headed for the second coffee house. There, Sly donned his disguise again and relieved the second guard, who was eager to eat his mother's spaghetti later on. While Bentley headed inside and stole the second blueprint, Sly pondered about what the guard said and declared that they would get something to eat after the mission.
Now there was only one coffee house left to hit, located across from the police station. After Sly gave the guard the correct password, the guard decided that it was not enough evidence that Sly was a guard. The guard asked Sly to tell him what his nickname was; he explained that he was the only guard with the name Tony B. and that he was a famous member of the mob family. Attempting to avoid answering the question, Sly responded that he was a new recruit from Rome. Tony, however, countered that he was well known in Rome, claiming that he was "practically the mayor of organized crime in Rome." Sly pretended that his phone rang, telling Tony that it might be the boss calling, before leaving the post.
Bentley suggested using the disguise to ask the other guards about Tony's nickname. Sly searched around and asked the guards, who revealed that Tony had a massive ego. Eventually, one of the guards told Sly that Tony's nickname was Tony "the Killer" B. Sly returned to Tony and gave his nickname. After taunting Sly about being on duty during Carnevale, Tony left and Bentley entered the coffee house. Once Bentley snagged the last blueprint, an alarm went off, revealing that the blueprint was rigged to the alarm. The alarm attracted a lot of guards to their location, forcing Sly to take off the disguise and keep the guards away from Bentley. Now that they obtained all of the blueprints, Bentley and Sly rushed back to the safe house to lose the guards.
- If the job is completed when there is at least one more job available before "Operation: Tar-Be Gone!", Bentley will say "Ah, the safety of the Safehouse." Otherwise, the slideshow for the operation will play.
- The paintings hiding the safes depict a lumberjack camp, a swamp and a gothic castle.
- Sly can speak to one of the guards to find out Tony B 's nickname he can speak to flash light guards or the cat rooftop guard can talk like the pigeon rooftop guard.