The reason why he's able to cross the riot line is because he meets up with the people he worked with before who would also get the same kind of jobs as he did. In other words, all of them are already experienced in dealing with the kind of CHAOS that they encountered during the riot (because when we first meet them they were also causing the same kind of CHAOS as part of their job). And then they also break down and through the BARRIERS that the cops put up.
The cop vehicle is also sitting there with several other vehicles just like it ... which may also mean the cops didn't feel the need to secure them ... because maybe with using that GIGANTIC HEAD-LESS ROBOT and the tear gas stuff ... they incorrectly assumed no one would be able to enter that area.
And, without the issue of a command (other than maybe clicking something on a device in her hand), we also saw DOLORES have a motorcycle drive itself over to her from a garage area. And that could also explain the reason why Caleb may have also had the same kind of code (or whatever it is) that could get the cop vehicle to take him to where he wants to go.
Or maybe he also had the option to either type in or give a VOICE activated command to the vehicle (maybe by simply typing or saying INCITE) telling it where to take him.
And since the other device that he has was also powerful enough to DESTROY that SPHERE called REHOBOAM (that was controlling everyone), one would also assume he'd have been given whatever other info he needed to be able to ensure that he could accomplish that mission.
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