Curate, connect, and discover
Part of the reason I want to write a fic focused on Cuff and Taylor is there seems to be some implication that Cuff is one of the closer members of the Chicago Wards to Weaver. Not enough to be considered a friend (I don’t think even Golem qualifies), but she does get picked for the Cauldron investigation strike team over most of the other members. A team Taylor seems to hold in fairly high regard (granted, Shadow Stalker and Lung make the list so again not a measure of friendship)
And one thing Arc 29 in particular does is have Cuff always seem to know how to get Taylor to listen to her and do what she wants.
Compare this to Arc 25 with Tecton spending basically half the chapter trying to convince Taylor and only getting a compromise. Though looking at the two conversations, there is a pretty distinct difference to their approach.
Tecton phrases a lot of the conversation under the idea of “we are x, so you should do this”. Sort of holding some level of authority in the fact they’ve been a team for so long. And, big shocker, Taylor isn’t exactly one for other people holding authority over her. She doesn’t really care for what she “owes” others based on their perceived relationship.
However, one thing about Taylor, at least to be gleaned from the earlier examples from Cuff, is that she does care to a degree about how she is perceived. This can be backed up in her conversation with Glenn in Arc 23
Bringing it back to the main topic, Cuff is, in essence, guilt tripping. The weaponized niceness bit (still one of my favorite Cuff moments ever), as well as the prisoner part, is basically making Taylor think “I’d be kind of an asshole if I didn’t do this”. There are some labels she’s fine with having, like “creepy”, but when it gets into some weirder territory as Cuff points out, she backs off.
I find it interesting that it’s specifically Cuff given these scenes with Taylor, especially this late into the story. It seems to establish at the very least that Cuff knows what makes Taylor tick, better than most of the other Wards.