" When is humility the wrong option? "
Jesus never did anything of Himself, but always as YHWH ABBA directed Him.
So humility is right only when it is obedient to YHWH,
and it is wrong when it is disobedient to YHWH.
(maybe also sin, but not necessarily, as it may be like when a little child is learning and gets mixed up)
Jesus often got "in trouble" in the real world, (but NEVER with YHWH),
as
did all the Apostles and disciples (sometimes with YHWH ) .
They denied themselves and did not "stand up for their rights" when wronged or robbed. Instead they often gave more to the robber ! as YHWH'S WORD says to do ! They cared not for prestige, position, or possessions,
not even for their own lives, but entrusted themselves and all their lives to YHWH ABBA by faith in Y'SHUA .