Did it work before you updated?

IIRC, it didn't, but I didn't really notice since I didn't have need for an interactive session (cpanp i module mostly just works) since I built it on 2011-08-10

cpan works, prompts me all normal like :)

Why do you have a $ command line prompt? Are you using MSWin32 Perl from inside Cygwin or some other UNIX-a-like environment like Interix (SUA)?

Nothing like that, its just my prompt :) cmd.exe prompt $$$S

More details like this would be appreciated

Such as? You can see perl -V here, only thing different in that version from this version, was addition of -static-libgcc -static-libstdc++ which caused different problem, but cpanp prompted.

Ok, here is another fun fact, the perl debugger (which I never use) won't start up either (perl -de 42) it goes into some kind of infinite loop while eating memory

All test suites pass, and these are the only hiccups I could find.

Actually, it reminds me of Faulting application perl.exe, version 0.0.0.0, faulting module msvcrt.dll, version 7.0.2600.1106, fault address 0x0003334c. but I hope its not something like that again.