Answer: if $a$ is a multiple of ${\rm gcd}(b,p^n)$, then yes; otherwise, no. Below, ${\rm gcd}$ means the greatest common divisor.
The tool you are missing is Bezout's identity:
For two nonzero integers $a,b$, there exists integers $x,y$ such that
$$ax+by={\rm gcd}(a,b)$$
and its corollary
As $x,y$ both run through every integer, $ax+by$ runs through precisely the multiples of ${\rm gcd}(a,b)$. In other words, each $ax+by$ is a multiple of ${\rm gcd}(a,b)$; conversely, each multiple of ${\rm gcd}(a,b)$ has the form $ax+by$.
Let's return to your original question. Use the corollary you get
$$a\equiv bx\pmod{p^n}\text{ has a solution}\\
\iff a-bx=p^ny\text{ for some integers }x,y\\
\iff a\text{ has the form }bx+p^ny\\
\iff a\text{ is a multiple of }{\rm gcd}(b,p^n)$$