I had (have, I suppose) the exact same problem on a number of builds of ActiveState Perl in Win2k. It is not a problem with the fonts, but, I believe the library they are linking with to render those fonts. My struggles with trying to resolve the issue left me with the distinct feeling that no one was interested in fixing the problem.

I was never able to fix the problem on Win32, but the identical code ran fine on Linux with the fonts copied over. This was after I took the time to manually download all of the dependent libraries (GD, freetype, etc) and rebuild/reinstall them. Perhaps if you have access to a build environment on Win you can have more luck.

Sorry I couldn't be of more help,
{NULE}

Update: I found my old demo code - again with the appropriate path and filenames this runs fine in Linux, but not win2k. Click on the read more tag for more info.

  $foo->set_font('font.ttf', 12) or die $gd_text->error;
  $foo->set_font(gdTinyFont);
  $foo->set_font(GD::Font::Tiny);
[download]

#!/usr/bin/perl

use strict;

use GD;
use GD::Text::Align;
use GD::Text::Wrap;

my $image = GD::Image->newFromJpeg('tv_click_no_words.jpg') || die();
my $black = $image->colorAllocate(0,0,0);

my $string = 'Dan is the best!';

# my @bounds = $image->stringTTF($black, '/home/dvf5907/gd/fonts/comic
+.ttf',
10, 0, 15,20, $string );

my $black = $image->colorAllocate(0,0,0);

# my $string = "Dan is the best!!!\nI'm the lizard king";
my $string = "hello?";

my $wrapbox = GD::Text::Wrap->new(
   $image,
   color => $black,
   text => $string
);

$wrapbox->font_path( 'C:/winnt/fonts' );
#work_area/mod_perl/dans_website/gd/fonts' );
$wrapbox->set_font('comic.ttf', 10) || die ();
$wrapbox->set(
  align => 'center',
  width => '122',
  preserve_nl => 1
);

$wrapbox->draw(10,5);
[download]