The problem is that 'User...' is not on a line by itself, but is part of a larger record, all on one line. In that case, you don't want the beginning-of-line anchor ^. Just allow it to match anywhere on the line, i.e. let it float:

my ($user, $group, $connected, $type) 
= $VAR2 =~ /User \[(\w+)\] Group \[(\w+)\] (\w+), Session Type: +(\w+)
+/;
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If you would like to learn more about the regex features I am using in this exmaple, check out the tutorial perlrequick.