diff --git a/t/filesystem.t b/t/filesystem.t
index 3b20acd..b07688d 100644
--- a/t/filesystem.t
+++ b/t/filesystem.t
@@ -417,10 +417,17 @@ SKIP: {
     $file->spew("Hello World\n");
     skip "symlink unavailable", 1 unless has_symlinks();
     eval { symlink $file => $link };
-    ok( $link->lstat->size, "lstat" );
-
-    is( $link->realpath, $file->realpath, "realpath resolves symlinks" );
-
+    if ($^O eq "MSWin32") {
+        ok( $link->lstat->size == 0, "lstat->size returns zero on Windows" );
+    }
+    else {
+        ok( $link->lstat->size, "lstat->size returns nonzero" );
+    }
+    SKIP: {
+        skip "realpath of symlink not working correctly on Windows for perl <= 5.37.5"
+           if $^O eq "MSWin32" and "$]" <= 5.037005;
+        is( $link->realpath, $file->realpath, "realpath resolves symlinks" );
+    }
     ok $link->remove, 'remove symbolic link';
     ok $file->remove;
 
diff --git a/t/symlinks.t b/t/symlinks.t
index 9e1a6f5..df907f4 100644
--- a/t/symlinks.t
+++ b/t/symlinks.t
@@ -19,12 +19,16 @@ subtest "relative symlinks with updir" => sub {
     my $foo = $td->child(qw/tmp foo/)->touch;
     my $bar = $td->child(qw/tmp tmp2 bar/);
 
-    symlink "../foo", $bar or die "Failed to symlink: $!\n";
+    my $relpath = "../foo";
+    # Account for a bug in Win32 API, see https://github.com/Perl/perl5/issues/20506
+    #  for more information
+    $relpath = "..\\foo" if $^O eq "MSWin32";
+    symlink $relpath, $bar or die "Failed to symlink: $!\n";
 
     ok -f $foo, "it's a file";
     ok -l $bar, "it's a link";
 
-    is readlink $bar, "../foo", "the link seems right";
+    is readlink $bar, $relpath, "the link seems right";
     is abs_path($bar), $foo, "abs_path gets's it right";
 
     is $bar->realpath, $foo, "realpath get's it right";