My blunt ... but, by no means intended to be “blunt” ... take on this is that:

You seem to have forgotten that Perl is a full-featured programming language ... not an over-glorified [Bash ...] script.   “Instead, Plan Accordingly.™”

For example:   “tailing a file” simply means:   seek( filehandle, distance, SEEK_END).   Nothing more, nothing less, no matter how “big” the file in-between might be.   We’ve been doing this sort of thing for random-access disk files since, uhh, the 1950’s.   Thus, the Perl programming language is quite able to solve this problem without resorting to any sort of “bash-script hack” metaphors ... and, so, you should do the same.

(No, I am not trying to make fun of you in a public place!!!   Please, let us herewith “put any egos aside,” and speak frankly as though we were not in-public.   I have no way of speaking that is not public.   “But, I digress™ ...”)

To solve your problem, you simply need to read “some n bytes” from the SEEK_END of the file in question, then use ordinary regular-expression logic against the buffer thusly obtained, in a loop, choosing the last match that you may find in such a loop, and taking a calculated risk that you didn’t happen to choose exactly the wrong starting-point.