Given (possibly non-Abelian) groups $H,G$ with $H \subseteq G$ and $f \in G$, I write $\langle H, f \rangle$ for the subgroup of $G$ generated by $H \cup \{f\}$.
Write $T(H)$ for the free product of $H$ with a multiplicative copy $y^{\mathbb{Z}}$ of the group of integers. We can represent a generic element $t(y)$ of $T(H)$ as a "term" $t(y) = h_0 y^{\alpha_0} \cdot \cdot \cdot h_n y^{\alpha_n}$ where $n \in \mathbb{N}$, $h_0,...,h_n \in H$ and $\alpha_0,...,\alpha_n \in \mathbb{Z}$. We set $t(f) := h_0 f^{\alpha_0} \cdot \cdot \cdot h_n f^{\alpha_n} \in G$ for this term.
Say that $f$ cancels a term over $H$ if there is a $t(y) \in T(H) \setminus \{1\}$ with $t(f)=1$. This is the case for instance if $f$ commutes with a non-trivial element of $H$.
Question: Is it the case that if $f$ cancels a term over $H$, then each element of $\langle H, f\rangle$ cancels a term over $H$?
I suspect not, but I don't have a way to produce a counterexample.