Playing with USSEP and Unofficial Creation Club Patch.
In the radiant quest to convince Roggi to stop worrying about paying Iddra back there is a bug dialogue in Roggi's side.
Basically, if one has done Roggi's personal quest before tackling Iddra's, one will not have to convince Roggi to give up (either by persuasion, intimidation, etc). Roggi will simply agree since he is your friend.
The problem is that I have done his personal quest and when I told him to stop worrying he agreed (like the wiki says; no need to convince him). BUT, I then had the option to persuade him in order to convince him to stop worrying (even though he already agreed to).
Picking the dialogue options, even though he is convinced, doesn't cause any problems except for being a nonsensical dialogue choice (and obviously a bug). Pressing exit when the dialogue appears doesn't change anything since the quest is completed (because you have done his personal mission and so he agrees without need to convince him).
All in all, it's a little bug that breaks immersion but doesn't cause any apparent gameplay problems.
Issue Data
Issue #32630: Roggi Knot-Beard quest dialogue shouldn't appear