diff --git a/Ombi.Services/Jobs/PlexUserChecker.cs b/Ombi.Services/Jobs/PlexUserChecker.cs
index d09bba28c..5ea9c74a7 100644
--- a/Ombi.Services/Jobs/PlexUserChecker.cs
+++ b/Ombi.Services/Jobs/PlexUserChecker.cs
@@ -97,13 +97,16 @@ namespace Ombi.Services.Jobs
                         var needToUpdate = false;
                         var usernameChanged = false;
 
-                        // Do we need up update any info?
-                        if (!dbUser.EmailAddress.Equals(user.Email, StringComparison.CurrentCultureIgnoreCase))
+                        if (!string.IsNullOrEmpty(user.Username)) // If true then this is a managed user, we do not want to update the email since Managed Users do not have email addresses
                         {
-                            dbUser.EmailAddress = user.Email;
-                            needToUpdate = true;
+                            // Do we need up update any info?
+                            if (!dbUser.EmailAddress.Equals(user.Email, StringComparison.CurrentCultureIgnoreCase))
+                            {
+                                dbUser.EmailAddress = user.Email;
+                                needToUpdate = true;
+                            }
                         }
-                        if (!dbUser.Username.Equals(user.Username, StringComparison.CurrentCultureIgnoreCase))
+                        if (!dbUser.Username.Equals(user.Title, StringComparison.CurrentCultureIgnoreCase))
                         {
                             needToUpdate = true;
                             usernameChanged = true;
@@ -114,8 +117,8 @@ namespace Ombi.Services.Jobs
                             if (usernameChanged)
                             {
                                 // The username has changed, let's check if the username matches any local users
-                                var localUser = localUsers.FirstOrDefault(x => x.UserName.Equals(user.Username, StringComparison.CurrentCultureIgnoreCase));
-                                dbUser.Username = user.Username;
+                                var localUser = localUsers.FirstOrDefault(x => x.UserName.Equals(user.Title, StringComparison.CurrentCultureIgnoreCase));
+                                dbUser.Username = user.Title;
                                 if (localUser != null)
                                 {
                                     // looks like we have a local user with the same name...
@@ -133,7 +136,7 @@ namespace Ombi.Services.Jobs
                                     var requestsWithThisUser = requests.Where(x => x.RequestedUsers.Contains(user.Username)).ToList();
                                     foreach (var r in requestsWithThisUser)
                                     {
-                                        r.RequestedUsers.Remove(user.Username); // Remove old
+                                        r.RequestedUsers.Remove(user.Title); // Remove old
                                         r.RequestedUsers.Add(dbUser.Username); // Add new
                                     }
 
@@ -157,7 +160,7 @@ namespace Ombi.Services.Jobs
                         Features = UserManagementHelper.GetFeatures(userManagementSettings),
                         UserAlias = string.Empty,
                         EmailAddress = user.Email,
-                        Username = user.Username,
+                        Username = user.Title,
                         LoginId = Guid.NewGuid().ToString()
                     };
 
diff --git a/Ombi.UI/Bootstrapper.cs b/Ombi.UI/Bootstrapper.cs
index cff531bd3..aa14ed0ab 100644
--- a/Ombi.UI/Bootstrapper.cs
+++ b/Ombi.UI/Bootstrapper.cs
@@ -97,6 +97,8 @@ namespace Ombi.UI
             ServicePointManager.SecurityProtocol = SecurityProtocolType.Tls;
             ServicePointManager.ServerCertificateValidationCallback +=
                  (sender, certificate, chain, sslPolicyErrors) => true;
+
+            ServicePointManager.Expect100Continue = false;
         }
 
 #if DEBUG
diff --git a/Ombi.UI/Content/app/userManagement/Directives/sidebar.html b/Ombi.UI/Content/app/userManagement/Directives/sidebar.html
index bb38289d1..799c133fe 100644
--- a/Ombi.UI/Content/app/userManagement/Directives/sidebar.html
+++ b/Ombi.UI/Content/app/userManagement/Directives/sidebar.html
@@ -39,7 +39,7 @@
             </div>
                 <strong>Email Address</strong>
                 <div class="form-group">
-                    <input id="emailAddress" type="email" ng-model="selectedUser.emailAddress" ng-disabled="selectedUser.type === 0" class="form-control form-control-custom" />
+                    <input id="emailAddress" type="email" ng-model="selectedUser.emailAddress" ng-disabled="selectedUser.emailDisabled" class="form-control form-control-custom" />
                 </div>
 
             <strong>Alias</strong>
diff --git a/Ombi.UI/Content/app/userManagement/userManagementController.js b/Ombi.UI/Content/app/userManagement/userManagementController.js
index de6c3f14f..56f68005e 100644
--- a/Ombi.UI/Content/app/userManagement/userManagementController.js
+++ b/Ombi.UI/Content/app/userManagement/userManagementController.js
@@ -31,6 +31,7 @@
             });
             $scope.selectedUser = user[0];
 
+            $scope.selectedUser.emailDisabled = $scope.selectedUser.type === 0 && $scope.selectedUser.managedUser == '';
             openSidebar();
         }
 
diff --git a/Ombi.UI/Models/UserManagement/UserManagementUsersViewModel.cs b/Ombi.UI/Models/UserManagement/UserManagementUsersViewModel.cs
index d6074babb..fa947e994 100644
--- a/Ombi.UI/Models/UserManagement/UserManagementUsersViewModel.cs
+++ b/Ombi.UI/Models/UserManagement/UserManagementUsersViewModel.cs
@@ -24,6 +24,7 @@ namespace Ombi.UI.Models.UserManagement
         public DateTime LastLoggedIn { get; set; }
         public List<CheckBox> Permissions { get; set; }
         public List<CheckBox> Features { get; set; }
+        public bool ManagedUser { get; set; }
     }
 
     public class UserManagementPlexInformation
diff --git a/Ombi.UI/Modules/UserManagementModule.cs b/Ombi.UI/Modules/UserManagementModule.cs
index bcf41d3a1..92d848606 100644
--- a/Ombi.UI/Modules/UserManagementModule.cs
+++ b/Ombi.UI/Modules/UserManagementModule.cs
@@ -231,6 +231,7 @@ namespace Ombi.UI.Modules
                 await UpdateRequests(plexDbUser.Username, plexDbUser.UserAlias, model.Alias);
 
                 plexDbUser.UserAlias = model.Alias;
+                plexDbUser.EmailAddress = model.EmailAddress;
 
                 await PlexUsersRepository.UpdateAsync(plexDbUser);
 
@@ -266,7 +267,7 @@ namespace Ombi.UI.Modules
                     UserAlias = model.Alias,
                     PlexUserId = plexUser.Id,
                     EmailAddress = plexUser.Email,
-                    Username = plexUser.Username,
+                    Username = plexUser.Title,
                     LoginId = Guid.NewGuid().ToString()
                 };
 
@@ -417,7 +418,7 @@ namespace Ombi.UI.Modules
                 Id = plexInfo.Id,
                 PermissionsFormattedString = newUser ? "Processing..." :( permissions == 0 ? "None" : permissions.ToString()),
                 FeaturesFormattedString = newUser ? "Processing..." : features.ToString(),
-                Username = plexInfo.Username,
+                Username = plexInfo.Title,
                 Type = UserType.PlexUser,
                 EmailAddress = plexInfo.Email,
                 Alias = dbUser?.UserAlias ?? string.Empty,
@@ -426,6 +427,7 @@ namespace Ombi.UI.Modules
                 {
                     Thumb = plexInfo.Thumb
                 },
+                ManagedUser = string.IsNullOrEmpty(plexInfo.Username)
             };
 
             m.Permissions.AddRange(GetPermissions(permissions));