diff --git a/src/DynamoCoreWpf/Controls/ShortcutToolbar.xaml b/src/DynamoCoreWpf/Controls/ShortcutToolbar.xaml
index 6f8e0bd51a4..4fcd1fdfa1f 100644
--- a/src/DynamoCoreWpf/Controls/ShortcutToolbar.xaml
+++ b/src/DynamoCoreWpf/Controls/ShortcutToolbar.xaml
@@ -141,7 +141,7 @@
                       Name="RightMenu">
                     <MenuItem Name="loginMenu" Margin="0,-3,-10,0">
                         <MenuItem.Header>
-                            <Button Name="LoginButton" Click="LoginButton_OnClick" Foreground="#DCDCDC"
+                            <Button Name="LoginButton" Click="LoginButton_OnClick" Foreground="#DCDCDC" ToolTipService.ShowOnDisabled="True"
                                     >
                                 <StackPanel FlowDirection="LeftToRight" Orientation="Horizontal">
 
@@ -210,7 +210,18 @@
 
                                 </Button.Style>
                                 <Button.ToolTip>
-                                    <ToolTip Content="{x:Static p:Resources.SignInButtonContentToolTip}" Style="{StaticResource GenericToolTipLight}"/>
+                                    <ToolTip>
+                                        <ToolTip.Style>
+                                            <Style TargetType="ToolTip" BasedOn="{StaticResource GenericToolTipLight}">
+                                                <Setter Property="Content" Value="{x:Static p:Resources.SignInButtonContentToolTip}" />
+                                                <Style.Triggers>
+                                                    <DataTrigger Binding="{Binding PlacementTarget.IsEnabled, RelativeSource={RelativeSource Self}}" Value="False">
+                                                        <Setter Property="Content" Value="{x:Static p:Resources.SignInOfflineButtonContentToolTip}" />
+                                                    </DataTrigger>
+                                                </Style.Triggers>
+                                            </Style>
+                                        </ToolTip.Style>
+                                    </ToolTip>
                                 </Button.ToolTip>
                             </Button>
                         </MenuItem.Header>
diff --git a/src/DynamoCoreWpf/Controls/ShortcutToolbar.xaml.cs b/src/DynamoCoreWpf/Controls/ShortcutToolbar.xaml.cs
index 041f7a33f5a..5c154ffe08a 100644
--- a/src/DynamoCoreWpf/Controls/ShortcutToolbar.xaml.cs
+++ b/src/DynamoCoreWpf/Controls/ShortcutToolbar.xaml.cs
@@ -79,6 +79,7 @@ private void ShortcutToolbar_Loaded(object sender, RoutedEventArgs e)
         {
             IsSaveButtonEnabled = false;
             IsExportMenuEnabled = false;
+            IsLoginMenuEnabled = !DynamoViewModel.Model.NoNetworkMode;
             DynamoViewModel.OnRequestShorcutToolbarLoaded(RightMenu.ActualWidth);
         }
 
diff --git a/src/DynamoCoreWpf/Properties/Resources.Designer.cs b/src/DynamoCoreWpf/Properties/Resources.Designer.cs
index a99c354141f..2984cd8ad3b 100644
--- a/src/DynamoCoreWpf/Properties/Resources.Designer.cs
+++ b/src/DynamoCoreWpf/Properties/Resources.Designer.cs
@@ -9978,6 +9978,15 @@ public static string SignInButtonContentToolTip {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Sign in to access online services that integrate with your desktop software..
+        /// </summary>
+        public static string SignInOfflineButtonContentToolTip {
+            get {
+                return ResourceManager.GetString("SignInOfflineButtonContentToolTip", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to Sign In.
         /// </summary>
diff --git a/src/DynamoCoreWpf/Properties/Resources.en-US.resx b/src/DynamoCoreWpf/Properties/Resources.en-US.resx
index cb3825e4480..5307cbe7a3c 100644
--- a/src/DynamoCoreWpf/Properties/Resources.en-US.resx
+++ b/src/DynamoCoreWpf/Properties/Resources.en-US.resx
@@ -151,6 +151,9 @@
   <data name="SignInButtonContentToolTip" xml:space="preserve">
     <value>Sign in to access online services that integrate with your desktop software.</value>
   </data>
+  <data name="SignInOfflineButtonContentToolTip" xml:space="preserve">
+    <value>Enable Network Mode to be able to sign in.</value>
+  </data>
   <data name="Autodesk360SignInButtonTitleToolTip" xml:space="preserve">
     <value>Autodesk A360</value>
   </data>
diff --git a/src/DynamoCoreWpf/Properties/Resources.resx b/src/DynamoCoreWpf/Properties/Resources.resx
index 2f4a4436efc..c96b709d4a2 100644
--- a/src/DynamoCoreWpf/Properties/Resources.resx
+++ b/src/DynamoCoreWpf/Properties/Resources.resx
@@ -2114,6 +2114,9 @@ Do you want to install the latest Dynamo update?</value>
   <data name="SignInButtonContentToolTip" xml:space="preserve">
     <value>Sign in to access online services that integrate with your desktop software.</value>
   </data>
+  <data name="SignInOfflineButtonContentToolTip" xml:space="preserve">
+    <value>Enable Network Mode to be able to sign in.</value>
+  </data>
   <data name="Autodesk360SignInButtonTitleToolTip" xml:space="preserve">
     <value>Autodesk A360</value>
   </data>
diff --git a/src/DynamoCoreWpf/PublicAPI.Unshipped.txt b/src/DynamoCoreWpf/PublicAPI.Unshipped.txt
index f25beca6bf6..6cc7d0155d4 100644
--- a/src/DynamoCoreWpf/PublicAPI.Unshipped.txt
+++ b/src/DynamoCoreWpf/PublicAPI.Unshipped.txt
@@ -5650,6 +5650,7 @@ static Dynamo.Wpf.Properties.Resources.SideBarPanelViewTitle.get -> string
 static Dynamo.Wpf.Properties.Resources.SignInButtonContentToolTip.get -> string
 static Dynamo.Wpf.Properties.Resources.SignInButtonText.get -> string
 static Dynamo.Wpf.Properties.Resources.SigningInButtonText.get -> string
+static Dynamo.Wpf.Properties.Resources.SignInOfflineButtonContentToolTip.get -> string
 static Dynamo.Wpf.Properties.Resources.SignOutConfirmationDialogText.get -> string
 static Dynamo.Wpf.Properties.Resources.SignOutConfirmationDialogTitle.get -> string
 static Dynamo.Wpf.Properties.Resources.SolutionToFolderNotWritatbleError.get -> string
diff --git a/src/DynamoCoreWpf/Views/Core/DynamoView.xaml.cs b/src/DynamoCoreWpf/Views/Core/DynamoView.xaml.cs
index a9d0838ad2a..b8d5389de50 100644
--- a/src/DynamoCoreWpf/Views/Core/DynamoView.xaml.cs
+++ b/src/DynamoCoreWpf/Views/Core/DynamoView.xaml.cs
@@ -377,6 +377,11 @@ private void DynamoViewModel_RequestEnableShortcutBarItems(bool enable)
                     shortcutBar.IsLoginMenuEnabled = true;
                     shortcutBar.IsNotificationCenterEnabled = true;
                 }
+
+                if (dynamoViewModel.Model.NoNetworkMode)
+                {
+                    shortcutBar.IsLoginMenuEnabled = false;
+                }
             }
         }