First of all, what exactly is $item?

If it is one line of the text (as in Blacadder code) then it will work fine, if it isn't, then it won't work fine.

If it contains more then one line, then you probalby want to make it a multi line regex, by adding the m modifier.

Also, I would suggest you read about 'Greedy' and/or 'Maximal Match' in the perlre pod and/or perlretut pod