OK, I've had time to look at it. I found the actual culprit, but at the same time, I found some more errors that affect other platforms as well.

The reason why it failed, is this snippet, at lines 237-239:

    if ($^O eq "MSWin32") {
        $fh = $_[0];
    }
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where later on, this is done with it:

    $fh = Compress::Zlib::gzdopen_ ($fh, $mode, 0)
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gzdopen_ is a low level function in Compress::Zlib. Well, guess what: this function expect a fileno, not a handle. So this fails. This does _drat() (it should either goto &_drat; or return _drat();, but not just call _drat()). $! is not set, so $error isn't set to a true value, and that's why it fails in such an ungraceful way. But I digress.

The solution is simple: set

    if ($^O eq "MSWin32") {
        $fh = fileno($_[0]);
    }
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instead. And now all tests succeed.

Here's the whole diff (for Archive-Tar-0.22.tar.gz):

--- Tar.pm  Fri Apr 28 00:50:16 2000
+++ blib/lib/Archive/Tar.pm Sat Aug 24 15:06:04 2002
@@ -79,7 +79,7 @@

 my $error;
 sub _drat {
-    $error = $! . '';
+    $error = $! . '' || 'unknown error';
     return;
 }

@@ -235,7 +235,7 @@
    or goto &_drat;

     if ($^O eq "MSWin32") {
-        $fh = $_[0];
+        $fh = fileno($_[0]);
     }
     else {
    $fh = fcntl ($_[0], F_DUPFD, 0)
@@ -248,7 +248,7 @@
 #  $fh = Compress::Zlib::gzopen ($_[0], $mode)
 #      or &_drat;
    $fh = Compress::Zlib::gzdopen_ ($fh, $mode, 0)
-            or &_drat;
+            or goto &_drat;
     }
     else {
    $flags = fcntl ($_[0], F_GETFL, 0) & (O_RDONLY | O_WRONLY | O_RDWR
+);
[download]

I'll try to warn the maintainer.