Yeah. Now that I've looked at it a bit more, something kinda like this should work:

$file =~ s/(\s+)($word)([\.\?\!]?\s+).*?(?!</a>)/"$1<a href=\"".$gloss
+ary{$word}{'link'}."\">$2<\/a>$3"/eig;
[download]

The .*(?!</a>) should then say that the engine will match the word plus (optionally) stuff after it unless that mess is ended by a </a>.

PerlStalker