diff --git a/static/directives/signup-form.html b/static/directives/signup-form.html
index 6430d2e16..e5ec7f75c 100644
--- a/static/directives/signup-form.html
+++ b/static/directives/signup-form.html
@@ -9,14 +9,12 @@
 
   <form class="form-signup" name="signupForm" ng-submit="register()" ng-show="!awaitingConfirmation && !registering">
     <label for="username">Username:</label>
-    <span class="namespace-input" binding="newUser.username" is-back-incompat="isBackIncompat" namespace-title="Requested username"></span>
+    <span class="namespace-input" binding="newUser.username" back-incompat-message="backIncompatMessage" namespace-title="Requested username"></span>
 
-    <div class="expandable" ng-class="{'expanded': isBackIncompat || (!signupForm.namespaceField.$error.required && signupForm.namespaceField.$invalid)}">
-      <div class="co-alert co-alert-warning thin" ng-show="isBackIncompat">
-        Usernames with dots or dashes are incompatible with Docker version 1.8 or older
-      </div>
+    <div class="expandable" ng-class="{'expanded': backIncompatMessage || (!signupForm.namespaceField.$error.required && signupForm.namespaceField.$invalid)}">
+      <div class="co-alert co-alert-warning thin" ng-show="backIncompatMessage">{{ backIncompatMessage }}</div>
       <div class="co-alert co-alert-danger thin" ng-show="!signupForm.namespaceField.$error.required && signupForm.namespaceField.$invalid">
-        Usernames must be alphanumeric and between four and thirty characters in length
+        Usernames must be alphanumeric and between 2 and 255 characters in length
       </div>
     </div>
 
diff --git a/static/js/app.js b/static/js/app.js
index fd163f262..650f6fe4d 100644
--- a/static/js/app.js
+++ b/static/js/app.js
@@ -1,6 +1,6 @@
 var TEAM_PATTERN = '^[a-z][a-z0-9]+$';
-var ROBOT_PATTERN = '^[a-z][a-z0-9_]{3,29}$';
-var USERNAME_PATTERN = '^(?=.{4,30}$)([a-z0-9]+(?:[._-][a-z0-9]+)*)$';
+var ROBOT_PATTERN = '^[a-z][a-z0-9_]{1,254}$';
+var USERNAME_PATTERN = '^(?=.{2,255}$)([a-z0-9]+(?:[._-][a-z0-9]+)*)$';
 
 // Define the pages module.
 quayPages = angular.module('quayPages', [], function(){});
diff --git a/static/js/directives/ui/namespace-input.js b/static/js/directives/ui/namespace-input.js
index 422539c12..c124c71ba 100644
--- a/static/js/directives/ui/namespace-input.js
+++ b/static/js/directives/ui/namespace-input.js
@@ -10,7 +10,7 @@ angular.module('quay').directive('namespaceInput', function () {
     restrict: 'C',
     scope: {
       'binding': '=binding',
-      'isBackIncompat': '=isBackIncompat',
+      'backIncompatMessage': '=backIncompatMessage',
       'hasExternalError': '=?hasExternalError',
 
       'namespaceTitle': '@namespaceTitle',
@@ -21,11 +21,17 @@ angular.module('quay').directive('namespaceInput', function () {
 
       $scope.$watch('binding', function(binding) {
         if (!binding) {
-          $scope.isBackIncompat = false;
+          $scope.backIncompatMessage = null;
           return;
         }
 
-        $scope.isBackIncompat = (binding.indexOf('-') > 0 || binding.indexOf('.') > 0);
+        if (binding.indexOf('-') > 0 || binding.indexOf('.') > 0) {
+          $scope.backIncompatMessage = 'Namespaces with dashes or dots are only compatible with Docker 1.9+';
+        } else if (binding.length < 4 || binding.length > 30) {
+          $scope.backIncompatMessage = 'Namespaces less than 4 or more than 30 characters are only compatible with Docker 1.6+';
+        } else {
+          $scope.backIncompatMessage = null;
+        }
       })
     }
   };
diff --git a/static/partials/new-organization.html b/static/partials/new-organization.html
index 359824673..4e5ea2a7c 100644
--- a/static/partials/new-organization.html
+++ b/static/partials/new-organization.html
@@ -42,16 +42,14 @@
                 <label for="orgName">Organization Name</label>
                 <div class="field-row">
                   <span class="field-container">
-                    <span class="namespace-input" binding="org.name" is-back-incompat="isBackIncompat" namespace-title="Organization name"></span>
-                  </span>
-                  <span class="co-alert co-alert-warning thin" ng-show="isBackIncompat">
-                    Organization names with dots or dashes are incompatible with Docker version 1.8 or older
+                    <span class="namespace-input" binding="org.name" back-incompat-message="backIncompatMessage" namespace-title="Organization name"></span>
                   </span>
+                  <span class="co-alert co-alert-warning thin" ng-show="backIncompatMessage">{{ backIncompatMessage }}</span>
                   <span class="co-alert co-alert-danger thin" ng-show="!newOrgForm.namespaceField.$error.required && newOrgForm.namespaceField.$invalid">
-                    Organization names must be alphanumeric, be at least four characters in length and max thirty characters in length
+                    Organization names must be alphanumeric, be at least 2 characters in length and max 255 characters in length
                   </span>
                 </div>
-                <span class="description">This will also be the namespace for your repositories. Must be alphanumeric, all lowercase, at least four characters long and at most thirty characters long.</span>
+                <span class="description">This will also be the namespace for your repositories. Must be alphanumeric, all lowercase, at least 2 characters long and at most 255 characters long.</span>
               </div>
 
               <div class="form-group nested" quay-require="['MAILING']">
diff --git a/static/partials/update-user.html b/static/partials/update-user.html
index a6a959acb..d4a2d298d 100644
--- a/static/partials/update-user.html
+++ b/static/partials/update-user.html
@@ -9,7 +9,7 @@
     </p>
     <p>Please confirm the selected username or enter a different username below:</p>
     <form name="usernameForm" ng-submit="updateUser({'username': username})">
-        <div class="namespace-input" binding="username" is-back-incompat="isBackIncompat"
+        <div class="namespace-input" binding="username" back-incompat-message="backIncompatMessage"
               namespace-title="Username" style="margin-bottom: 20px;"
               has-external-error="state == 'existing'"></div>
 
@@ -17,7 +17,7 @@
                ng-disabled="usernameForm.$invalid || state != 'confirmed'"
                value="Confirm Username">
         <span class="cor-loader-inline" ng-show="state == 'confirming'"></span>
-        <span class="username-status" ng-show="state == 'confirmed' && !isBackIncompat">
+        <span class="username-status" ng-show="state == 'confirmed' && !backIncompatMessage">
             <i class="fa fa-check-circle"></i> Username valid
         </span>
         <span class="username-status" ng-show="state == 'existing'">
@@ -29,8 +29,8 @@
         <span class="username-status" ng-show="state == 'editing' && usernameForm.$invalid">
             Usernames must be alphanumeric and be at least four characters in length
         </span>
-        <span class="username-status" ng-show="state == 'confirmed' && isBackIncompat">
-            <i class="fa fa-exclamation-triangle"></i> Note: Usernames with dots or dashes are incompatible with Docker version 1.8 or older
+        <span class="username-status" ng-show="state == 'confirmed' && backIncompatMessage">
+            <i class="fa fa-exclamation-triangle"></i>{{ backIncompatMessage }}
         </span>
     </form>
 </div>
diff --git a/test/test_api_usage.py b/test/test_api_usage.py
index 31d101c5b..500d0d424 100644
--- a/test/test_api_usage.py
+++ b/test/test_api_usage.py
@@ -651,7 +651,7 @@ class TestCreateNewUser(ApiTestCase):
                                            email='test@example.com'),
                                  expected_code=400)
 
-    self.assertEquals('Invalid namespace a: Namespace must be between 4 and 30 characters in length',
+    self.assertEquals('Invalid namespace a: Namespace must be between 2 and 255 characters in length',
                       json['detail'])
 
   def test_trycreateregexmismatch(self):
diff --git a/test/test_util.py b/test/test_util.py
index 42724bb61..f7b6cc6f1 100644
--- a/test/test_util.py
+++ b/test/test_util.py
@@ -20,6 +20,8 @@ class TestUsernameValidation(unittest.TestCase):
     self.assertFalse(result)
 
   def test_valid(self):
+    self.assertValid('ja')
+    self.assertValid('jak')
     self.assertValid('jake')
     self.assertValid('ja_ke')
     self.assertValid('te-st')
@@ -27,14 +29,13 @@ class TestUsernameValidation(unittest.TestCase):
 
   def test_properlength(self):
     self.assertValid('z' * 30)
+    self.assertValid('z' * 255)
 
   def test_tooshort(self):
     self.assertInvalid('j')
-    self.assertInvalid('ja')
-    self.assertInvalid('jk')
 
   def test_toolong(self):
-    self.assertInvalid('z' * 31)
+    self.assertInvalid('z' * 256)
 
   def test_invalids(self):
     self.assertInvalid('_test')
@@ -158,20 +159,21 @@ class TestUsernameGenerator(unittest.TestCase):
     self.assert_generated_output('ja___ke', 'ja_ke')
 
   def test_trailing_underscores(self):
-    self.assert_generated_output('ja__', 'ja00')
+    self.assert_generated_output('ja__', 'ja')
     self.assert_generated_output('jake__', 'jake')
 
   def test_starting_underscore(self):
     self.assert_generated_output('_jake', 'jake')
 
   def test_short_names(self):
-    self.assert_generated_output('a', 'a000')
-    self.assert_generated_output('ab', 'ab00')
-    self.assert_generated_output('abc', 'abc0')
+    self.assert_generated_output('a', 'a0')
+    self.assert_generated_output('ab', 'ab')
+    self.assert_generated_output('abc', 'abc')
 
   def test_long_names(self):
     self.assert_generated_output('abcdefghijklmnopqrstuvwxyz1234567890',
-                                 'abcdefghijklmnopqrstuvwxyz1234')
+                                 'abcdefghijklmnopqrstuvwxyz1234567890')
+    self.assert_generated_output('c' * 256, 'c' * 255)
 
   def test_unicode_transliteration(self):
     self.assert_generated_output(u'\xc6neid', 'aeneid')
@@ -184,18 +186,18 @@ class TestUsernameGenerator(unittest.TestCase):
     self.assert_generated_output(u'\u0985\u09ad\u09bf\u099c\u09c0\u09a4', 'abhijiit')
     self.assert_generated_output(u'\u0d05\u0d2d\u0d3f\u0d1c\u0d40\u0d24', 'abhijiit')
     self.assert_generated_output(u'\u0d2e\u0d32\u0d2f\u0d3e\u0d32\u0d2e\u0d4d', 'mlyaalm')
-    self.assert_generated_output(u'\ue000', '0000')
-    self.assert_generated_output(u'\u03ff', '0000')
+    self.assert_generated_output(u'\ue000', '00')
+    self.assert_generated_output(u'\u03ff', '00')
 
     self.assert_generated_output(u'\u0d2e\u0d32\u03ff\u03ff\u0d2e\u0d32', 'mlml')
 
   def test_multiple_suggestions(self):
     name_gen = generate_valid_usernames('a')
     generated_output = list(islice(name_gen, 4))
-    self.assertEquals('a000', generated_output[0])
-    self.assertEquals('a001', generated_output[1])
-    self.assertEquals('a002', generated_output[2])
-    self.assertEquals('a003', generated_output[3])
+    self.assertEquals('a0', generated_output[0])
+    self.assertEquals('a1', generated_output[1])
+    self.assertEquals('a2', generated_output[2])
+    self.assertEquals('a3', generated_output[3])
 
 
 class TestDockerVersionParsing(unittest.TestCase):
diff --git a/util/validation.py b/util/validation.py
index 9be53e43d..92d766159 100644
--- a/util/validation.py
+++ b/util/validation.py
@@ -9,8 +9,8 @@ INVALID_PASSWORD_MESSAGE = 'Invalid password, password must be at least ' + \
                            '8 characters and contain no whitespace.'
 VALID_CHARACTERS = string.digits + string.lowercase
 
-MIN_USERNAME_LENGTH = 4
-MAX_USERNAME_LENGTH = 30
+MIN_USERNAME_LENGTH = 2
+MAX_USERNAME_LENGTH = 255
 
 VALID_LABEL_KEY_REGEX = r'^[a-z0-9](([a-z0-9]|[-.](?![.-]))*[a-z0-9])?$'
 VALID_USERNAME_REGEX = r'^([a-z0-9]+(?:[._-][a-z0-9]+)*)$'
@@ -63,7 +63,7 @@ def _gen_filler_chars(num_filler_chars):
 
 def generate_valid_usernames(input_username):
   normalized = input_username.encode('unidecode', 'ignore').strip().lower()
-  prefix = re.sub(INVALID_USERNAME_CHARACTERS, '_', normalized)[:30]
+  prefix = re.sub(INVALID_USERNAME_CHARACTERS, '_', normalized)[:MAX_USERNAME_LENGTH]
   prefix = re.sub(r'_{2,}', '_', prefix)
 
   if prefix.endswith('_'):