use strict;
my $str = 'https://test.com/plants/ice/flag/237468372912873
https://test.com/plants/extra/ice/flag/237468372912873
https://test.com/plants/ice/flag/extra/237468372912873
https://test.com/plants/ice/flag/extra/extra/237468372912873
https://test.com/plants/ice/flag/extra/237468372912873?paramOne=1¶mTwo=2/12#someHash
https://test.com/plants/not_ice/flag/237468372912873';
my $regex = qr/(\/ice\/flag\/(?:[^?#\n]*\/)?)[^\/#?\n]+/mp;
my $subst = '$1redacted';
my $result = $str =~ s/$regex/$subst/rg;
print "The result of the substitution is' $result\n";
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Perl, please visit: http://perldoc.perl.org/perlre.html