Word maps have been studied for matrix groups over a field. We initiate the study of problems related to word maps in the context of the group $\mathrm{GL}_n(\mathscr O_2)$, where $\mathscr O_2$ is a finite local principal ideal ring of length two (e.g. $\mathbb{Z}/p^2\mathbb{Z}$ and $\mathbb F_q[t]/\langle t^2\rangle$). We study the power map $g\mapsto g^L$, where $L$ is a positive integer. We consider $L$ to be coprime to $p$ (an odd prime), the characteristic of the residue field $k$ of $\mathscr O_2$. We classify all the elements in the image, whose mod-$\mathfrak m$ reduction in $\mathrm{GL}_n(k)$ are either regular semisimple or cyclic, where $\mathfrak m$ is the unique maximal ideal of $\mathscr O_2$. Our main tool is a Hensel lifting for polynomial equations over $\mathrm{M}_n(\mathscr O_2)$, which we establish in this work. A central contribution of this work is the construction of canonical forms for certain natural classes of matrices over $\mathscr O_2$. As applications, we derive explicit generating functions for the probabilities that a random element of $\mathrm{GL}_n(\mathscr O_2)$ is regular semisimple, $L$-power regular semisimple, compatible cyclic, or $L$-power compatible cyclic.