diff --git a/letsencrypt/plugins/webroot.py b/letsencrypt/plugins/webroot.py
index 4e83d04ea..ac4c3c1ec 100644
--- a/letsencrypt/plugins/webroot.py
+++ b/letsencrypt/plugins/webroot.py
@@ -15,6 +15,7 @@ from acme import challenges
 from letsencrypt import cli
 from letsencrypt import errors
 from letsencrypt import interfaces
+from letsencrypt.display import util as display_util
 from letsencrypt.plugins import common
 
 
@@ -34,6 +35,9 @@ necessary validation resources to appropriate paths on the file
 system. It expects that there is some other HTTP server configured
 to serve all files under specified web root ({0})."""
 
+    _INTERACTIVE_CANCEL = ("Every requested domain must have a "
+                           "webroot when using the webroot plugin.")
+
     def more_info(self):  # pylint: disable=missing-docstring,no-self-use
         return self.MORE_INFO.format(self.conf("path"))
 
@@ -80,17 +84,40 @@ to serve all files under specified web root ({0})."""
             for achall in achalls:
                 self.conf("map").setdefault(achall.domain, webroot_path)
         else:
-            known_webroots = list(six.itervalues(self.conf("map")))
+            known_webroots = list(set(six.itervalues(self.conf("map"))))
             for achall in achalls:
                 if achall.domain not in self.conf("map"):
-                    self._prompt_for_webroot(achall.domain, known_webroots)
+                    new_webroot = self._prompt_for_webroot(achall.domain,
+                                                           known_webroots)
+                    try:
+                        known_webroots.remove(new_webroot)
+                    except ValueError:
+                        pass
+                    known_webroots.append(new_webroot)
+                    self.conf("map")[achall.domain] = new_webroot
 
     def _prompt_for_webroot(self, domain, known_webroots):
         display = zope.component.getUtility(interfaces.IDisplay)
-        display.menu(
+        code, index = display.menu(
             "Select the webroot for {0}:".format(domain),
-            ["Enter a new webroot"] + known_webroots,
-            help_label="Help")
+            ["Enter a new webroot"] + known_webroots[::-1])
+        if code == display_util.CANCEL:
+            raise errors.PluginError(self._INTERACTIVE_CANCEL)
+        elif index != 0:
+            return known_webroots[index - 1]
+
+        while True:
+            code, webroot = display.directory_select(
+                "Input the webroot for {0}:".format(domain))
+            if code == display_util.CANCEL:
+                raise errors.PluginError(self._INTERACTIVE_CANCEL)
+            elif code == display_util.HELP:
+                display.notification(display_util.DSELECT_HELP)
+            else:
+                try:
+                    return _validate_webroot(webroot)
+                except errors.PluginError:
+                    pass
 
     def _create_challenge_dirs(self):
         path_map = self.conf("map")