It's interesting, Edward tasked Leo to describe the attitude and the true thoughts about subject X, but Leo instead describes the attitude and thoughts of subject X:

"Rigid, prescriptive, and linear. To the Architect, there is only one correct “path” up the tower, and any deviation is viewed not as a choice, but as a “defect” or “failure of will.” [...] The attitude is one of benevolent tyranny. Subject X believes they are doing what is best for the Primary Subject, but their definition of “best” is entirely self-serving—the subject’s success is a reflection of the Architect’s own greatness."

"To Subject X, the Primary Subject is a mirror designed to reflect the Architect’s own glory. Therefore, the subject’s current rebellion is viewed not as a cry for help, but as a “betrayal of the plan.” The relation is entirely parasitic, though the Architect is convinced it is parental/mentoring."

Given that this information is crucial, I don't think that Leo made a mistake.

I still see the possibility that Courtney was talking to different factions without recognizing that they are different factions.

The "Commander" never fit into the bigger picture.