I'm going to release Perl 5.40.0 to Cygwin in a few days. I've skipped 5.38 in order to update only every second year (which I've done since the 5.22 release). I haven't seen any trouble in my own Perl distribution packages from the update even though there are lots of them that haven't been updated since at least 5.22. So I hope it will be smooth sailing for anything else depending on Perl also.
Any maintainer having packages that depend on perl5_036 or below should re-release or upgrade these soon-ish after the Perl update is available, as otherwise users are either blocked from upgrading Perl or will have to uninstall the affected packages. The rebuilt packages need to have a dependency on perl5_040, which cygport provides automatically when building with the new Perl. Packages that need an update from perl5_036 are: biber nginx-mod_http_perl perl-Barcode-ZBar perl-Chemistry-OpenBabel perl-clinkgrammar perl-Graphics-Magick perl-gv perl-Image-Magick perl-marisa perl-ming perl-Net-Libproxy perl-net-snmp perl-openwsman perl-solv perl-Stow perl-Wx-build perl-Xfce4-Xfconf perl-zinnia po4a subversion-perl Achim. -- +<[Q+ Matrix-12 WAVE#46+305 Neuron microQkb Andromeda XTk Blofeld]>+ SD adaptations for KORG EX-800 and Poly-800MkII V0.9: http://Synth.Stromeko.net/Downloads.html#KorgSDada