Man that works sweet. Except the comments by themselves of course. I raped your code and implemented it in what I was doing and it works pretty good. It solved 2 of my problems at once. The commented text and the coloring on input. I am going to work on the comments by themselves in a little bit. I will post back if I come up with an answer. Edit 1:Got the code working with comments without keywords on same line.

#!/usr/bin/winperl
use strict;
use warnings;

use Tk;

our @Red_Keywords = qw(print sprintf);

our @Blue_Keywords = qw(if elsif else my our use sub);

our $Comment = '#|//';

our @Comment = ("\#", "\//");

our $All_Keys = "print|sprintf|if|elsif|else|my|our|use|sub|while|fore
+ach|loop|split|
                 glob|substr|length|open|close|chomp|chop|next|unless"
+;

our %Highlights = (
  Red_Keyword  => [qw(red bold)],
  Blue_Keyword => [qw(blue bold)],
  Comment      => [qw(orange italic)],
);

setup_window();

MainLoop;



sub setup_window {
  my $mw = MainWindow->new();
  my $t  = $mw->Scrolled('Text', -font => ['Courier New', 10])->pack()
+;

  $t->tagConfigure('blue',   -foreground => 'blue');
  $t->tagConfigure('red',    -foreground => 'red');
  $t->tagConfigure('orange', -foreground => 'orange');
  $t->tagConfigure('gray',   -foreground => 'gray');

  $t->tagConfigure('bold',   -font => ['Courier New', 10, 'bold']);
  $t->tagConfigure('italic', -font => ['Courier New', 10, 'italic']);

  $t->bind(
    '<KeyRelease>',
    # Automatically prepends $t to called sub's args
    [\&highlight_range, 'insert linestart', 'insert lineend'],
  );

  # Paste events may include more than one line to be formatted,
  # so we rehighlight the entire text.
  $t->bind(
    '<<Paste>>',
    [\&highlight_range, '1.0', 'end'],
  );

  $t->focus();
}

# Remove all formatting so that updates will unhighlight things proper
+ly
sub unhighlight_range {
  my $t     = shift;
  my $start = shift;
  my $end   = shift;

  foreach my $style (keys %Highlights) {
    foreach my $tag (@{$Highlights{$style}}) {
      $t->tagRemove($tag, $start, $end);
    }
  }
}

sub highlight_range {
  my $t     = shift;
  my $start = shift;
  my $end   = shift;

  unhighlight_range($t, $start, $end);

  foreach my $comm (@Comment) {
     my $word_len = length $comm;
     my $next = $start;
     while (my $comment = $t->search(-regexp => $comm, $next, $end)) {
        $next = "$comment + $word_len chars";

        # Search for a keyword on the same line
      
        my $from = $t->search(-regexp, "\\b\Q$All_Keys\E\\b", "$commen
+t linestart" => "$comment lineend");
     
        if($comment and !$from) {
           mark_word($t, $comment, "$comment lineend", 'Comment');
        }
     }
  }

  foreach my $word (@Red_Keywords) {
    my $word_len = length $word;
    my $next = $start;
    while (my $from = $t->search(-regexp, "\\b\Q$word\E\\b", $next, $e
+nd)) {
      $next = "$from + $word_len chars";

      # Search for a comment character on the same line
      my $comment = $t->search(
        -regexp => $Comment,
        "$from linestart" => "$from lineend"
      );

      # If comment found and is before keyword, skip formatting
      unless($comment and $t->compare($comment, '<', $from)) {
        mark_word($t, $from, $next, 'Red_Keyword');
      }

      if($comment) {
        mark_word($t, $comment, "$comment lineend", 'Comment');
      }
    }
  }

  foreach my $word (@Blue_Keywords) {
    my $word_len = length $word;
    my $next = $start;
    while (my $from = $t->search(-regexp, "\\b\Q$word\E\\b", $next, $e
+nd)) {
      $next = "$from + $word_len chars";

      # Search for a comment character on the same line
      my $comment = $t->search(
        -regexp => $Comment,
        "$from linestart" => "$from lineend"
      );

      # If comment found and is before keyword, skip formatting
      unless($comment and $t->compare($comment, '<', $from)) {
        mark_word($t, $from, $next, 'Blue_Keyword');
      }

      if($comment) {
        mark_word($t, $comment, "$comment lineend", 'Comment');
      }
    }
  }
}

sub mark_word {
  my $text  = shift;
  my $start = shift;
  my $end   = shift;
  my $style = shift;

  return unless exists $Highlights{$style};

  foreach my $tag (@{$Highlights{$style}}) {
    $text->tagAdd($tag, $start, $end);
  }
}
[download]

Thanx again for the great input!

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