If $G$ is a group and $g_1, g_2 \in G$ let us write $g_1 \sim g_2$ if there is an automorphism $\alpha \in \operatorname{Aut}(G)$ such that $g_1^\alpha = g_2$.
Let $F = F_2$ be the free group on two generators. Let $(\gamma_n(F))_{n=1}^\infty$ denote the lower central series of $F$. Let $w_1, w_2 \in F$. Suppose that, for every integer $n$, $$(w_1 \bmod \gamma_n(F)) \sim (w_2 \bmod \gamma_n(F)).$$ Does it follow that $w_1 \sim w_2$?
This question is interesting to me because a positive answer sounds too good to be true, and yet equally I would be fascinated to see an offending pair of words $w_1, w_2$. Not sure if there is research out there about this.