Let $G$ be a finite group acting freely on a path connected topological space $X$. The covering map $X \to X/G$ induces a long exact sequence of homotopy groups. Since $\pi_1(G) = 1$ and $\pi_0(X) = 0$, we obtain a short exact sequence $$ 1 \to \pi_1(X) \to \pi_1(X/G) \to G \to 0. $$ The last map here, call it $\partial$, is in principle only a map between pointed sets.
Baby question: Is $\partial$ always a group homomorphism?
Question: If $\partial$ is a group homomorphism, then the above is a short exact sequence of groups. Is it always non-split? (Assuming of course that $G, \pi_1(X) \neq 1$. I am most interested in the case when $\pi_1(X) = \mathbf{Z}$.)
Let $X=S^1\times S^\infty\to X/G=S^1\times\mathbb{RP}^\infty$ where $G=\mathbb Z/2$. Then the short exact sequence is $0\to\mathbb {Z}\to\mathbb {Z}\times\mathbb{Z}/2\to\mathbb Z/2\to 0$, which is split.