diff --git a/windows/src/desktop/kmshell/main/Keyman.Configuration.UI.UfrmStartInstall.dfm b/windows/src/desktop/kmshell/main/Keyman.Configuration.UI.UfrmStartInstall.dfm
index 0ca96f7123..592245267b 100644
--- a/windows/src/desktop/kmshell/main/Keyman.Configuration.UI.UfrmStartInstall.dfm
+++ b/windows/src/desktop/kmshell/main/Keyman.Configuration.UI.UfrmStartInstall.dfm
@@ -4,8 +4,8 @@ object frmStartInstall: TfrmStartInstall
   BorderIcons = [biSystemMenu]
   BorderStyle = bsDialog
   Caption = 'Keyman Update'
-  ClientHeight = 142
-  ClientWidth = 322
+  ClientHeight = 201
+  ClientWidth = 393
   Color = clBtnFace
   Font.Charset = DEFAULT_CHARSET
   Font.Color = clWindowText
@@ -17,33 +17,149 @@ object frmStartInstall: TfrmStartInstall
   PixelsPerInch = 96
   TextHeight = 13
   object lblInstallUpdate: TLabel
-    Left = 72
-    Top = 48
-    Width = 180
-    Height = 19
-    Caption = 'Keyman update available.'
-    Font.Charset = DEFAULT_CHARSET
+    Left = 87
+    Top = 81
+    Width = 218
+    Height = 65
+    Caption = 'An update to Keyman has been downloaded and is ready to install.'
+    Font.Charset = ANSI_CHARSET
     Font.Color = clWindowText
-    Font.Height = -16
-    Font.Name = 'Tahoma'
+    Font.Height = -13
+    Font.Name = 'Segoe UI'
     Font.Style = []
     ParentFont = False
+    WordWrap = True
+  end
+  object imgKeymanLogo: TImage
+    Left = 8
+    Top = 8
+    Width = 201
+    Height = 43
+    Picture.Data = {
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+      98415417C2E0E8C19CBB4D8AFB1B5615F5AC8096334DFFFF67301700D248D081
+      307494BBC0334D052CFED3AFB79C66E97F565266B13BCE11904F41D2E2B6A07E
+      ABDFF44AC33003247912AC03CC95ADAD855BD52A541A062D2D260D8396169386
+      414B8B49C3A0A5C5A461D0D262FA3F82D7F60E256D51F10000000049454E44AE
+      426082}
   end
   object cmdInstall: TButton
-    Left = 140
-    Top = 104
+    Left = 188
+    Top = 168
     Width = 75
     Height = 25
-    Caption = 'Update'
+    Caption = 'Update now'
     ModalResult = 1
     TabOrder = 0
   end
   object cmdLater: TButton
-    Left = 234
-    Top = 104
+    Left = 298
+    Top = 168
     Width = 75
     Height = 25
-    Caption = 'Close'
+    Caption = 'Later'
     ModalResult = 8
     TabOrder = 1
   end
diff --git a/windows/src/desktop/kmshell/main/Keyman.Configuration.UI.UfrmStartInstall.pas b/windows/src/desktop/kmshell/main/Keyman.Configuration.UI.UfrmStartInstall.pas
index b2353bc6fd..f4ca051c32 100644
--- a/windows/src/desktop/kmshell/main/Keyman.Configuration.UI.UfrmStartInstall.pas
+++ b/windows/src/desktop/kmshell/main/Keyman.Configuration.UI.UfrmStartInstall.pas
@@ -19,13 +19,14 @@ uses
   Winapi.Messages,
   Winapi.Windows,
   UfrmKeymanBase,
-  UserMessages;
+  UserMessages, Vcl.Imaging.pngimage;
 
 type
   TfrmStartInstall = class(TfrmKeymanBase)
     cmdInstall: TButton;
     cmdLater: TButton;
     lblInstallUpdate: TLabel;
+    imgKeymanLogo: TImage;
     procedure FormCreate(Sender: TObject);
   private
   public
@@ -42,8 +43,8 @@ uses
 procedure TfrmStartInstall.FormCreate(Sender: TObject);
 begin
   inherited;
-  cmdInstall.Caption := MsgFromId(S_Update);
-  cmdLater.Caption := MsgFromId(S_Button_Close);
+  cmdInstall.Caption := MsgFromId(S_Update_Now);
+  cmdLater.Caption := MsgFromId(S_Later);
   lblInstallUpdate.Caption := MsgFromId(S_Ready_To_Install);
 end;
 
diff --git a/windows/src/desktop/kmshell/main/initprog.pas b/windows/src/desktop/kmshell/main/initprog.pas
index 829183b8ed..e19a9db358 100644
--- a/windows/src/desktop/kmshell/main/initprog.pas
+++ b/windows/src/desktop/kmshell/main/initprog.pas
@@ -433,6 +433,9 @@ begin
   Application.HelpFile := GetCHMPath; // may change if language changes
   Application.Title := MsgFromId(SKApplicationTitle);
 
+  if (FMode in [fmStart, fmBoot]) then FIcon := 'appicon.ico'
+  else FIcon := 'cfgicon.ico';
+
   if GetOS in [osOther] then
   begin
     ShowMessage(MsgFromId(SKOSNotSupported));
@@ -460,9 +463,6 @@ begin
 
   // I1818 - remove start mode change
 
-  if (FMode in [fmStart, fmBoot]) then FIcon := 'appicon.ico'
-  else FIcon := 'cfgicon.ico';
-
   FIcon := GetDebugPath(FIcon, ExtractFilePath(ParamStr(0)) + FIcon, False);
   if FileExists(FIcon) then
     Application.Icon.LoadFromFile(FIcon);
diff --git a/windows/src/desktop/kmshell/xml/strings.xml b/windows/src/desktop/kmshell/xml/strings.xml
index 73b9831c3b..a50d161382 100644
--- a/windows/src/desktop/kmshell/xml/strings.xml
+++ b/windows/src/desktop/kmshell/xml/strings.xml
@@ -601,7 +601,7 @@
   <!-- Context: Configuration Dialog - Update on boot pop up -->
   <!-- String Type: PlainText -->
   <!-- Introduced: 18.0.168 -->
-  <string name="S_Ready_To_Install" comment="Update on boot pop up - inform user update about to install">Keyman Update ready to install.</string>
+  <string name="S_Ready_To_Install" comment="Update on boot pop up - inform user update about to install">An update to Keyman has been downloaded and is ready to install.</string>
 
   <!-- Context: Download Keyboard Dialog -->
   <!-- String Type: PlainText -->
@@ -732,6 +732,11 @@ keyboard that you use in Windows.  Keyman keyboards will adapt automatically to
   <!-- Introduced: 18.0.230.0 -->
   <string name="S_Update" comment="Update tab name">Update</string>
 
+  <!-- Context: Online Update Dialog -->
+  <!-- String Type: PlainText -->
+  <!-- Introduced: 18.0.230.0 -->
+  <string name="S_Update_Now" comment="Update now button">Update Now</string>
+
   <!-- Context: Online Update Dialog -->
   <!-- String Type: PlainText -->
   <!-- Introduced: 7.0.230.0 -->
@@ -820,7 +825,10 @@ keyboard that you use in Windows.  Keyman keyboards will adapt automatically to
   <!-- Introduced: 8.0.288.0 -->
   <string name="SKUpdate_IconMenuExit" comment="Update icon - exit menu item">E&amp;xit online update check</string>
 
-
+  <!-- Context: Install Dialog -->
+  <!-- String Type: FormatString -->
+  <!-- Introduced: 17.0233.0 -->
+  <string name="S_Later" comment="Apply Update Later">Later</string>
 
   <!-- Context: Update Dialog -->
   <!-- String Type: FormatString -->