I think it shouldn't be defined as $\pi/2$ is not in the range of the function $\sec^{-1}(x)$
Wolfram confused me by giving the answer as $\pi/2$ : Link
But it mentions on another page that $\pi/2$ is not in the range of $\sec^{-1}(x)$: Link
What is the correct answer?
$\sec (\frac \pi 2)$ is not defined, so any expression that uses it is undefined. Alpha is pattern matching, using $\sec^{-1}(\sec(x))=x$, which is true for most $x$. It is often sloppy on cases like this.