SE 20.0.1.3 64-bit Windows 7 Hotfix 7
It looks like automatic dynamic surround isn't working for several constructs Perl constructs which used to work in 2013 and 2014. I didn't check all constructs but for sure "while" and "foreach" constructs are not automatic in 2015. I have "Use Dynamic Surround" and "Auto-Surround" enabled.
While researching this problem, I noticed that the manual invocation of "dynamic-surround" does not work for the following variation of the foreach construct:
foreach my $item (@items)
{
}