diff --git a/lib/WebGUI/Asset.pm b/lib/WebGUI/Asset.pm
index 8baaad444..9147c8c77 100644
--- a/lib/WebGUI/Asset.pm
+++ b/lib/WebGUI/Asset.pm
@@ -528,7 +528,17 @@ sub fixTitle {
 
 =head2 fixUrl ( string )
 
-Returns a URL, removing invalid characters and making it unique.
+Returns a URL, removing invalid characters and making it unique by
+adding a digit to the end if necessary.  URLs are not allowed to be
+children of the extrasURL, the uploadsURL, or any defined passthruURL.
+If not URL is passed, a URL will be constructed from the Asset's
+parent and the menuTitle.
+
+Assets have a maximum length of 250 characters.  Any URL longer than
+250 characters will be truncated to the initial 220 characters.
+
+URLs will be passed through $session->url->urlize to make them WebGUI compliant.
+That includes any languages specific constraints set up in the default language pack.
 
 =head3 string
 
@@ -550,12 +560,20 @@ sub fixUrl {
 
 	# fix urls used by uploads and extras
 	# and those beginning with http
-	my @badUrls = ($self->session->config->get("extrasURL"), $self->session->config->get("uploadsURL"));
-	foreach my $badUrl (@badUrls) {
+	my @badUrls = (
+        $self->session->config->get("extrasURL"),
+        $self->session->config->get("uploadsURL"),
+    );
+    if (defined $self->session->config->get('passthruUrls')) {
+        push @badUrls, @{ $self->session->config->get('passthruUrls') };
+    }
+    foreach my $badUrl (@badUrls) {
+        $badUrl =~ s{ / $ }{}x; # Remove trailing slashes from the end of the URL
 		if ($badUrl =~ /^http/) {
-			$badUrl =~ s/^http.*\/(.*)$/$1/;
-		} else {
-			$badUrl =~ s/^\/(.*)/$1/;
+			$badUrl =~ s{ ^ http .* / } {}x; #Remove everything but the final path fragment from the badUrl
+		}
+        else {
+			$badUrl =~ s{ ^ / }{}x; #Remove leading slashes from bare URLs
 		}
 		if ($url =~ /^$badUrl/) {
 			$url = "_".$url;
@@ -581,17 +599,18 @@ sub fixUrl {
 	}
 
 	# check to see if the url already exists or not, and increment it if it does
-        if ($self->urlExists($self->session, $url, {assetId=>$self->getId})) {
-                my @parts = split(/\./,$url);
-                if ($parts[0] =~ /(.*)(\d+$)/) {
-                        $parts[0] = $1.($2+1);
-                } else {
-                        $parts[0] .= "2";
-                }
-                $url = join(".",@parts);
-                $url = $self->fixUrl($url);
+    if ($self->urlExists($self->session, $url, {assetId=>$self->getId})) {
+        my @parts = split(/\./,$url);
+        if ($parts[0] =~ /(.*)(\d+$)/) {
+            $parts[0] = $1.($2+1);
         }
-	return $url;
+        else {
+            $parts[0] .= "2";
+        }
+        $url = join(".",@parts);
+        $url = $self->fixUrl($url);
+    }
+    return $url;
 }
 
 
diff --git a/lib/WebGUI/Session/Url.pm b/lib/WebGUI/Session/Url.pm
index d92459dd7..e6705c219 100644
--- a/lib/WebGUI/Session/Url.pm
+++ b/lib/WebGUI/Session/Url.pm
@@ -140,7 +140,7 @@ sub extras {
     my $self = shift;
     my $path = shift;
     my $url = $self->session->config->get("extrasURL").'/'.$path;
-    $url =~ s$(?<!^http:)/{2,}$/$g;
+    $url =~ s$(?<!^http:)/{2,}$/$g;  ##Remove //, unless it's part of http://
     return $url;
 }
 
diff --git a/t/Asset/Asset.t b/t/Asset/Asset.t
index 35e5e7d10..984626e26 100644
--- a/t/Asset/Asset.t
+++ b/t/Asset/Asset.t
@@ -17,7 +17,7 @@ use WebGUI::Session;
 use WebGUI::Asset;
 use WebGUI::Asset::Wobject::Navigation;
 
-use Test::More tests => 32; # increment this value for each test you create
+use Test::More tests => 39; # increment this value for each test you create
 use Test::MockObject;
 
 my $session = WebGUI::Test->session;
@@ -147,4 +147,37 @@ $session->{_request} = $origRequest;
 #
 ################################################################
 
-is($importNode->fixUrl('1234'.'-'x250 . 'abcdefghijkl'), '1234'.'-'x216, 'fixUrl truncates to 220 characters');
+is($importNode->fixUrl('1234'.'-'x235 . 'abcdefghij'), '1234'.'-'x235 . 'abcdefghij', 'fixUrl leaves long URLs under 250 characters alone');
+is($importNode->fixUrl('1234'.'-'x250 . 'abcdefghij'), '1234'.'-'x216, 'fixUrl truncates long URLs over 250 characters to 220 characters');
+
+my $origExtras   = $session->config->get('extrasURL');
+my $origUploads  = $session->config->get('uploadsURL');
+my $origPassthru = $session->config->get('passthruUrls');
+
+$session->config->set('extrasURL',    '/extras');
+$session->config->set('uploadsURL',   '/uploads');
+$session->config->set('passthruUrls', [qw/pass1 pass2/]);
+
+is($importNode->fixUrl('/extras'),  '_extras',  'underscore prepended to URLs that match the extrasURL');
+is($importNode->fixUrl('/uploads'), '_uploads', 'underscore prepended to URLs that match the uploadsURL');
+is($importNode->fixUrl('/pass1'),   '_pass1',   'underscore prepended to URLs that match any passthruUrl 1');
+is($importNode->fixUrl('/pass2'),   '_pass2',   'underscore prepended to URLs that match any passthruUrl 2');
+
+#Now that we have verified that extrasURL and uploadsURL both work, just test one.
+$session->config->set('extrasURL',  '/extras1/');
+is($importNode->fixUrl('/extras1'), '_extras1', 'trailing underscore in extrasURL does not defeat the check');
+
+$session->config->set('extrasURL',  'http://mysite.com/extras2');
+is($importNode->fixUrl('/extras2'), '_extras2', 'underscore prepended to URLs that match the extrasURL, even with http://');
+
+END: {
+
+    $session->config->set('extrasURL',    $origExtras);
+    $session->config->set('uploadsURL',   $origUploads);
+    if (defined $origPassthru) {
+        $session->config->set('passthruUrls', $origPassthru);
+    }
+    else {
+        $session->config->delete('passthruUrls');
+    }
+}