We study singularity properties of word maps on semisimple Lie algebras, semisimple algebraic groups and matrix algebras and obtain various applications to random walks induced by word measures on compact p p -adic groups. Given a word w w in a free Lie algebra L r \mathcal {L}_{r} , it induces a word map φ w : g r → g \varphi _{w}:\mathfrak {g}^{r}\rightarrow \mathfrak {g} for every semisimple Lie algebra g \mathfrak {g} . Given two words w 1 ∈ L r 1 w_{1}\in \mathcal {L}_{r_{1}} and w 2 ∈ L r 2 w_{2}\in \mathcal {L}_{r_{2}} , we define and study the convolution of the corresponding word maps φ w 1 ∗ φ w 2 ≔ φ w 1 + φ w 2 : g r 1 + r 2 → g \varphi _{w_{1}}*\varphi _{w_{2}}≔\varphi _{w_{1}}+\varphi _{w_{2}}:\mathfrak {g}^{r_{1}+r_{2}}\rightarrow \mathfrak {g} . By introducing new degeneration techniques, we show that for any word w ∈ L r w\in \mathcal {L}_{r} of degree d d , and any simple Lie algebra g \mathfrak {g} with φ w ( g r ) ≠ 0 \varphi _{w}(\mathfrak {g}^{r})\neq 0 , one obtains a flat morphism with reduced fibers of rational singularities (abbreviated an (FRS) morphism) after taking O ( d 4 ) O(d^{4}) self-convolutions of φ w \varphi _{w} . Similar results are obtained for matrix word maps. We deduce that a group word map of length ℓ \ell becomes (FRS), locally around identity, after O ( ℓ 4 ) O(\ell ^{4}) self-convolutions, for every semisimple algebraic group G _ \underline {G} . We furthermore provide uniform lower bounds on the log canonical threshold of the fibers of Lie algebra, matrix and group word maps. For the commutator word w 0 = [ X , Y ] w_{0}=[X,Y] , we show that φ w 0 ∗ 4 \varphi _{w_{0}}^{*4} is (FRS) for any semisimple Lie algebra, improving a result of Aizenbud-Avni, and obtaining applications in representation growth of compact p p -adic and arithmetic groups. The singularity properties we consider, such as the (FRS) property, are intimately connected to the point count of fibers over finite rings of the form Z / p k Z \mathbb {Z}/p^{k}\mathbb {Z} . This allows us to relate them to properties of some natural families of random walks on finite and compact p p -adic groups. We explore these connections, characterizing some of the singularity properties discussed in probabilistic terms, and provide applications to p p -adic probabilistic Waring type problems.