diff --git a/code/forms/SiteTreeURLSegmentField.php b/code/forms/SiteTreeURLSegmentField.php
new file mode 100644
index 00000000..0d5a32f2
--- /dev/null
+++ b/code/forms/SiteTreeURLSegmentField.php
@@ -0,0 +1,42 @@
+<?php
+/**
+ * @package cms
+ * @subpackage forms
+ */
+
+/**
+ * Used to edit the SiteTree->URLSegment property, and suggest input based on the serverside rules
+ * defined through {@link SiteTree->generateURLSegment()} and {@link URLSegmentFilter}.
+ * 
+ * Note: The actual conversion for saving the value takes place in the model layer.
+ */
+class SiteTreeURLSegmentField extends TextField {
+	
+	static $allowed_actions = array(
+		'suggest'
+	);
+	
+	function suggest($request) {
+		if(!$request->getVar('value')) return $this->httpError(405);
+		$page = $this->getPage();
+
+		// Same logic as SiteTree->onBeforeWrite
+		$page->URLSegment = $page->generateURLSegment($request->getVar('value'));
+		$count = 2;
+		while(!$page->validURLSegment()) {
+			$page->URLSegment = preg_replace('/-[0-9]+$/', null, $page->URLSegment) . '-' . $count;
+			$count++;
+		}
+		
+		Controller::curr()->getResponse()->addHeader('Content-Type', 'application/json');
+		return Convert::raw2json(array('value' => $page->URLSegment));
+	}
+		
+	/**
+	 * @return SiteTree
+	 */
+	function getPage() {
+		$idField = $this->getForm()->dataFieldByName('ID');
+		return ($idField && $idField->Value()) ? DataObject::get_by_id('SiteTree', $idField->Value()) : singleton('SiteTree');
+	}
+}
\ No newline at end of file
diff --git a/code/model/SiteTree.php b/code/model/SiteTree.php
index 506d9e72..0f492bbe 100644
--- a/code/model/SiteTree.php
+++ b/code/model/SiteTree.php
@@ -1385,7 +1385,7 @@ class SiteTree extends DataObject implements PermissionProvider,i18nEntityProvid
 		if((!$this->URLSegment || $this->URLSegment == 'new-page') && $this->Title) {
 			$this->URLSegment = $this->generateURLSegment($this->Title);
 		} else if($this->isChanged('URLSegment')) {
-			$filter = Object::create('URLPathFilter');
+			$filter = Object::create('URLSegmentFilter');
 			$this->URLSegment = $filter->filter($this->URLSegment);
 			// If after sanitising there is no URLSegment, give it a reasonable default
 			if(!$this->URLSegment) $this->URLSegment = "page-$this->ID";
@@ -1578,7 +1578,7 @@ class SiteTree extends DataObject implements PermissionProvider,i18nEntityProvid
 	 * @return string Generated url segment
 	 */
 	function generateURLSegment($title){
-		$filter = Object::create('URLPathFilter');
+		$filter = Object::create('URLSegmentFilter');
 		$t = $filter->filter($title);
 		
 		// Fallback to generic page name if path is empty (= no valid, convertable characters)
@@ -1828,7 +1828,7 @@ class SiteTree extends DataObject implements PermissionProvider,i18nEntityProvid
 					new HtmlEditorField("Content", _t('SiteTree.HTMLEDITORTITLE', "Content", PR_MEDIUM, 'HTML editor title'))
 				),
 				$tabMeta = new Tab('Metadata',
-					new TextField("URLSegment", $this->fieldLabel('URLSegment') . $urlHelper),
+					new SiteTreeURLSegmentField("URLSegment", $this->fieldLabel('URLSegment') . $urlHelper),
 					new LiteralField('LinkChangeNote', self::nested_urls() && count($this->Children()) ?
 						'<p>' . $this->fieldLabel('LinkChangeNote'). '</p>' : null
 					),
diff --git a/javascript/CMSMain.EditForm.js b/javascript/CMSMain.EditForm.js
index 2aa16f92..9c191369 100644
--- a/javascript/CMSMain.EditForm.js
+++ b/javascript/CMSMain.EditForm.js
@@ -21,23 +21,6 @@
 		 * Input validation on the URLSegment field
 		 */
 		$('.cms-edit-form input[name=URLSegment]').entwine({
-			/**
-			 * Property: FilterRegex
-			 * Regex
-			 */
-			FilterRegex: /[^A-Za-z0-9-]+/,
-
-			/**
-			 * Property: ValidationMessage
-			 * String
-			 */
-			ValidationMessage: ss.i18n._t('CMSMAIN.URLSEGMENTVALIDATION'),
-			
-			/**
-			 * Property: MaxLength
-			 * Int
-			 */
-			MaxLength: 50,
 	
 			/**
 			 * Constructor: onmatch
@@ -47,42 +30,41 @@
 		
 				// intercept change event, do our own writing
 				this.bind('change', function(e) {
-					if(!self.validate()) {
-						jQuery.noticeAdd(self.getValidationMessage());
-					}
-					self.val(self.suggestValue(e.target.value));
-					return false;
+					if(!self.val()) return;
+					
+					self.attr('disabled', 'disabled').parents('.field:first').addClass('loading');
+					var oldVal = self.val();
+					self.suggest(oldVal, function(data) {
+						self.removeAttr('disabled').parents('.field:first').removeClass('loading');
+						var newVal = decodeURIComponent(data.value);
+						self.val(newVal);
+						
+						if(oldVal != newVal) {
+							jQuery.noticeAdd(ss.i18n._t('The URL has been changed'));
+						}
+					});
+					
 				});
 				
 				this._super();
 			},
 	
 			/**
-			 * Function: suggestValue
+			 * Function: suggest
 			 *  
 			 * Return a value matching the criteria.
 			 * 
 			 * Parameters:
 			 *  (String) val
-			 * 
-			 * Returns:
-			 *  String
+			 *  (Function) callback
 			 */
-			suggestValue: function(val) {
-				// TODO Do we want to enforce lowercasing in URLs?
-				return val.substr(0, this.getMaxLength()).replace(this.getFilterRegex(), '').toLowerCase();
-			},
-	
-			/**
-			 * Function: validate
-			 * 
-			 * Returns:
-			 *  Boolean
-			 */
-			validate: function() {
-				return (
-					this.val().length > this.getMaxLength()
-					|| this.val().match(this.getFilterRegex())
+			suggest: function(val, callback) {
+				$.get(
+					this.parents('form:first').attr('action') + 
+						'/field/URLSegment/suggest/?value=' + encodeURIComponent(this.val()),
+					function(data) {
+						callback.apply(this, arguments);
+					}
 				);
 			}
 		});
@@ -114,24 +96,21 @@
 			 */
 			updateURLSegment: function(field) {
 				if(!field || !field.length) return;
+				
+				// TODO The new URL value is determined asynchronously,
+				// which means we need to come up with an alternative system
+				// to ask user permission to change it.
 		
 				// TODO language/logic coupling
 				var isNew = this.val().indexOf("new") == 0;
-				var suggestion = field.entwine('ss').suggestValue(this.val());
-				var confirmMessage = ss.i18n.sprintf(
-					ss.i18n._t(
-						'UPDATEURL.CONFIRM', 
-						'Would you like me to change the URL to:\n\n' 
-						+ '%s/\n\nClick Ok to change the URL, '
-						+ 'click Cancel to leave it as:\n\n%s'
-					),
-					suggestion,
-					field.val()
+				var confirmMessage = ss.i18n._t(
+					'UPDATEURL.CONFIRMSIMPLE', 
+					'Do you want to update the URL from your new page title?'
 				);
 
 				// don't ask for replacement if record is considered 'new' as defined by its title
-				if(isNew || (suggestion != field.val() && confirm(confirmMessage))) {
-					field.val(suggestion);
+				if(isNew || confirm(confirmMessage)) {
+					field.val(this.val()).trigger('change');
 				}
 			}
 		});