diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index 0df1e528ecf..54147edb1f3 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -186,6 +186,12 @@ jobs:
 
 - job: BuildWindowsMSI
   displayName: Build Windows MSI
+  strategy:
+    matrix:
+      x86:
+        Platform: x86
+      x64:
+        Platform: x64
 
   dependsOn: ExtractMetadata
   condition: succeeded()
@@ -200,6 +206,7 @@ jobs:
 
 
   - script: |
+      set ARCH=$(Platform)
       set /p CLI_VERSION=<$(System.ArtifactsDirectory)/metadata/version
       set
       
@@ -215,10 +222,16 @@ jobs:
     displayName: 'Publish Artifact: MSI'
     inputs:
       TargetPath: 'build_scripts/windows/out/'
-      ArtifactName: msi
+      ArtifactName: msi-$(Platform)
 
 - job: TestWindowsMSI
   displayName: Test Windows MSI
+  strategy:
+    matrix:
+      x86:
+        Platform: x86
+      x64:
+        Platform: x64
 
   dependsOn: BuildWindowsMSI
   condition: and(succeeded(), in(variables['Build.Reason'], 'IndividualCI', 'BatchedCI', 'Manual', 'Schedule'))
@@ -235,7 +248,7 @@ jobs:
     displayName: 'Download Build Artifacts'
     inputs:
       TargetPath: '$(Build.ArtifactStagingDirectory)/msi'
-      artifactName: msi
+      artifactName: msi-$(Platform)
 
   - task: PowerShell@2
     displayName: Install and Load CLI
diff --git a/build_scripts/windows/Product.wxs b/build_scripts/windows/Product.wxs
index b8b7d8d6a8b..2db951f4a06 100644
--- a/build_scripts/windows/Product.wxs
+++ b/build_scripts/windows/Product.wxs
@@ -7,19 +7,61 @@
   <?define ProductDescription = "Command-line tools for Azure." ?>
   <?define ProductAuthor = "Microsoft Corporation" ?>
   <?define ProductResources = ".\resources\" ?>
+  <?define UpgradeCode32 = "dff82af0-3f95-4ac9-8efd-948604fdb028" ?>
+
+  <?if $(var.Platform) = "x64" ?>
+  <?define AzureCliRegistryGuid = "90b6367e-4e15-4313-af33-a0ef459a56fc" ?>
+  <?define AzureCliSystemPathGuid = "12c8f0dc-0475-4814-93b6-fcbe82e89532" ?>
+  <?define AzureCliVersionGuid = "4df4882f-4604-4cdc-a0b4-bffc4b8c5967" ?>
+  <?define ProgramFilesFolder = "ProgramFiles64Folder" ?>
+  <?define RemoveAzureCLIFolderGuid = "7ce8a521-7429-4ded-9cce-0948e393cc83" ?>
+  <?define RemoveCLIFolderGuid = "59fb416c-91d0-49aa-a185-d4330c435a93" ?>
+  <?define UpgradeCode = "90762fec-9554-4729-a107-c6a8ea316698" ?>
+  <?define Architecture = "64-bit" ?>
+
+  <?elseif $(var.Platform) = "x86" ?>
+  <?define AzureCliRegistryGuid = "BDEEE50E-70D3-4990-BFF9-FCF8114AA701" ?>
+  <?define AzureCliSystemPathGuid = "3B60CA67-DB92-465A-BC96-3CA6CAEFF41B" ?>
+  <?define AzureCliVersionGuid = "A5647E93-02B7-4CED-802A-DDD7416E0231" ?>
+  <?define ProgramFilesFolder = "ProgramFilesFolder" ?>
+  <?define RemoveAzureCLIFolderGuid = "6AF97701-6A7A-4292-95D6-ED34CD4C97C0" ?>
+  <?define RemoveCLIFolderGuid = "24DA394D-B03D-4623-A0D9-852DB51EF9F4" ?>
+  <?define UpgradeCode = $(var.UpgradeCode32) ?>
+  <?define Architecture = "32-bit" ?>
+
+  <?else ?>
+  <?error Unsupported platform "$(var.Platform)" ?>
+  <?endif ?>
 
   <Product Id="*"
-           Name="$(var.ProductName)"
+           Name="$(var.ProductName) ($(var.Architecture))"
            Language="1033"
            Version="$(var.ProductVersion)"
            Manufacturer="$(var.ProductAuthor)"
-           UpgradeCode="dff82af0-3f95-4ac9-8efd-948604fdb028">
+           UpgradeCode="$(var.UpgradeCode)">
 
     <Package InstallerVersion="200"
              Compressed="yes"
              InstallScope="perMachine" />
 
-    <MajorUpgrade DowngradeErrorMessage="A newer version of [ProductName] is already installed." Schedule="afterInstallExecute" />
+    <Upgrade Id="$(var.UpgradeCode)">
+      <UpgradeVersion Property="WIX_UPGRADE_DETECTED" Maximum="$(var.ProductVersion)" IncludeMaximum="no" MigrateFeatures="yes" />
+      <UpgradeVersion Property="WIX_DOWNGRADE_DETECTED" Minimum="$(var.ProductVersion)" IncludeMinimum="no" OnlyDetect="yes" />
+    </Upgrade>
+    <InstallExecuteSequence>
+      <RemoveExistingProducts After="InstallExecute" />
+    </InstallExecuteSequence>
+
+    <!-- New product architectures should upgrade the original x86 product - even of the same version. -->
+    <?if $(var.UpgradeCode) != $(var.UpgradeCode32) ?>
+    <Upgrade Id="$(var.UpgradeCode32)">
+      <UpgradeVersion Property="WIX_X86_UPGRADE_DETECTED" Maximum="$(var.ProductVersion)" IncludeMaximum="yes" MigrateFeatures="yes" />
+      <UpgradeVersion Property="WIX_X86_DOWNGRADE_DETECTED" Minimum="$(var.ProductVersion)" IncludeMinimum="no" OnlyDetect="yes" />
+    </Upgrade>
+    <Condition Message="A newer version of $(var.ProductName) is already installed.">NOT (WIX_DOWNGRADE_DETECTED OR WIX_X86_DOWNGRADE_DETECTED)</Condition>
+    <?else ?>
+    <Condition Message="A newer version of $(var.ProductName) is already installed.">NOT WIX_DOWNGRADE_DETECTED</Condition>
+    <?endif ?>
 
     <Media Id="1" Cabinet="WindowsAzureCLI.cab" EmbedCab="yes" CompressionLevel="high" />
 
@@ -61,7 +103,7 @@
 
   <Fragment>
     <Directory Id="TARGETDIR" Name="SourceDir">
-      <Directory Id="ProgramFilesFolder">
+      <Directory Id="$(var.ProgramFilesFolder)">
         <Directory Id="SDKFOLDER" Name="Microsoft SDKs">
           <Directory Id="AZUREFOLDER" Name="Azure">
             <Directory Id="AZURECLIFOLDER" Name="CLI2">
@@ -78,17 +120,17 @@
     <ComponentGroup Id="AzureCliSettingsGroup">
       <Component Id="RemoveCLIFolder"
                  Directory="DynamicCliDir"
-                 Guid="{24DA394D-B03D-4623-A0D9-852DB51EF9F4}">
+                 Guid="$(var.RemoveCLIFolderGuid)">
         <RemoveFolder Id="DynamicCliDir" On="uninstall" />
       </Component>
       <Component Id="RemoveAzureCLIFolder"
                  Directory="AZURECLIFOLDER"
-                 Guid="{6AF97701-6A7A-4292-95D6-ED34CD4C97C0}">
+                 Guid="$(var.RemoveAzureCLIFolderGuid)">
         <RemoveFolder Id="AZURECLIFOLDER" On="uninstall" />
       </Component>
       <Component Id="AzureCliSystemPath"
                  Directory="DynamicCliDir"
-                 Guid="{3B60CA67-DB92-465A-BC96-3CA6CAEFF41B}">
+                 Guid="$(var.AzureCliSystemPathGuid)">
         <Environment Id="AzureCliAddedToPATH"
                      Name="PATH"
                      Value="[DynamicCliDir]wbin"
@@ -100,7 +142,7 @@
       </Component>
       <Component Id="AzureCliRegistry"
                  Directory="DynamicCliDir"
-                 Guid="{BDEEE50E-70D3-4990-BFF9-FCF8114AA701}">
+                 Guid="$(var.AzureCliRegistryGuid)">
         <RegistryValue Root="HKCU"
                        Key="Software\Microsoft\$(var.ProductName)"
                        Name="installed"
@@ -110,7 +152,7 @@
       </Component>
       <Component Id="AzureCliVersion"
                  Directory="DynamicCliDir"
-                 Guid="{A5647E93-02B7-4CED-802A-DDD7416E0231}">
+                 Guid="$(var.AzureCliVersionGuid)">
         <RegistryValue Root="HKLM"
                        Key="Software\Microsoft\$(var.ProductName)"
                        Name="version"
diff --git a/build_scripts/windows/azure-cli.sln b/build_scripts/windows/azure-cli.sln
index 73dd3a6ed7d..fa338bf49a3 100644
--- a/build_scripts/windows/azure-cli.sln
+++ b/build_scripts/windows/azure-cli.sln
@@ -7,12 +7,18 @@ Global
 	GlobalSection(SolutionConfigurationPlatforms) = preSolution
 		Debug|x86 = Debug|x86
 		Release|x86 = Release|x86
+		Debug|x64 = Debug|x64
+		Release|x64 = Release|x64
 	EndGlobalSection
 	GlobalSection(ProjectConfigurationPlatforms) = postSolution
 		{9A0DC66D-3186-4EE4-B471-6C0F1DD6E159}.Debug|x86.ActiveCfg = Debug|x86
 		{9A0DC66D-3186-4EE4-B471-6C0F1DD6E159}.Debug|x86.Build.0 = Debug|x86
 		{9A0DC66D-3186-4EE4-B471-6C0F1DD6E159}.Release|x86.ActiveCfg = Release|x86
 		{9A0DC66D-3186-4EE4-B471-6C0F1DD6E159}.Release|x86.Build.0 = Release|x86
+		{9A0DC66D-3186-4EE4-B471-6C0F1DD6E159}.Debug|x64.ActiveCfg = Debug|x64
+		{9A0DC66D-3186-4EE4-B471-6C0F1DD6E159}.Debug|x64.Build.0 = Debug|x64
+		{9A0DC66D-3186-4EE4-B471-6C0F1DD6E159}.Release|x64.ActiveCfg = Release|x64
+		{9A0DC66D-3186-4EE4-B471-6C0F1DD6E159}.Release|x64.Build.0 = Release|x64
 	EndGlobalSection
 	GlobalSection(SolutionProperties) = preSolution
 		HideSolutionNode = FALSE
diff --git a/build_scripts/windows/azure-cli.wixproj b/build_scripts/windows/azure-cli.wixproj
index 2805978b135..e0497237fbd 100644
--- a/build_scripts/windows/azure-cli.wixproj
+++ b/build_scripts/windows/azure-cli.wixproj
@@ -1,14 +1,5 @@
 <?xml version="1.0" encoding="utf-8"?>
 <Project ToolsVersion="4.0" DefaultTargets="Build" xmlns="http://schemas.microsoft.com/developer/msbuild/2003">
-  <!-- Local WiX -->
-  <PropertyGroup>
-    <LocalWixRoot>artifacts\wix\</LocalWixRoot>
-    <WixToolPath>$(LocalWixRoot)</WixToolPath>
-    <WixTargetsPath>$(WixToolPath)Wix.targets</WixTargetsPath>
-    <WixTasksPath>wixtasks.dll</WixTasksPath>
-    <AzureCliSource>artifacts\cli</AzureCliSource>
-    <LinkerAdditionalOptions>-fv</LinkerAdditionalOptions>
-  </PropertyGroup>
   <!-- Project -->
   <PropertyGroup>
     <Configuration Condition=" '$(Configuration)' == '' ">Debug</Configuration>
@@ -21,6 +12,15 @@
     <WixTargetsPath Condition=" '$(WixTargetsPath)' == '' AND '$(MSBuildExtensionsPath32)' != '' ">$(MSBuildExtensionsPath32)\Microsoft\WiX\v3.x\Wix.targets</WixTargetsPath>
     <WixTargetsPath Condition=" '$(WixTargetsPath)' == '' ">$(MSBuildExtensionsPath)\Microsoft\WiX\v3.x\Wix.targets</WixTargetsPath>
   </PropertyGroup>
+  <!-- Local WiX -->
+  <PropertyGroup>
+    <LocalWixRoot>artifacts\wix</LocalWixRoot>
+    <WixToolPath>$(MSBuildThisFileDirectory)$(LocalWixRoot)</WixToolPath>
+    <WixTargetsPath Condition="Exists('$(WixToolPath)\Wix.targets')">$(WixToolPath)\Wix.targets</WixTargetsPath>
+    <WixTasksPath Condition="Exists('$(WixToolPath)\wixtasks.dll')">$(WixToolPath)\wixtasks.dll</WixTasksPath>
+    <AzureCliSource>artifacts\cli</AzureCliSource>
+    <LinkerAdditionalOptions>-fv</LinkerAdditionalOptions>
+  </PropertyGroup>
   <PropertyGroup Condition=" '$(Configuration)|$(Platform)' == 'Debug|x86' ">
     <OutputPath>out\$(Configuration)\</OutputPath>
     <IntermediateOutputPath>out\obj\$(Configuration)\</IntermediateOutputPath>
@@ -31,6 +31,16 @@
     <IntermediateOutputPath>out\obj\$(Configuration)\</IntermediateOutputPath>
     <DefineConstants>AzureCliSource=$(AzureCliSource)</DefineConstants>
   </PropertyGroup>
+  <PropertyGroup Condition=" '$(Configuration)|$(Platform)' == 'Debug|x64' ">
+    <OutputPath>out\$(Configuration)\</OutputPath>
+    <IntermediateOutputPath>out\obj\$(Configuration)\</IntermediateOutputPath>
+    <DefineConstants>Debug;AzureCliSource=$(AzureCliSource)</DefineConstants>
+  </PropertyGroup>
+  <PropertyGroup Condition=" '$(Configuration)|$(Platform)' == 'Release|x64' ">
+    <OutputPath>out\</OutputPath>
+    <IntermediateOutputPath>out\obj\$(Configuration)\</IntermediateOutputPath>
+    <DefineConstants>AzureCliSource=$(AzureCliSource)</DefineConstants>
+  </PropertyGroup>
   <ItemGroup>
     <Compile Include="out\azure-cli.wxs">
       <Link>azure-cli.wxs</Link>
@@ -55,4 +65,4 @@
   <Target Name="BeforeBuild">
     <HeatDirectory Directory="$(AzureCliSource)" ToolPath="$(WixToolPath)" AutogenerateGuids="true" ComponentGroupName="AzureCliComponentGroup" SuppressRootDirectory="true" DirectoryRefId="DynamicCliDir" OutputFile="out\azure-cli.wxs" PreprocessorVariable="var.AzureCliSource" />
   </Target>
-</Project>
\ No newline at end of file
+</Project>
diff --git a/build_scripts/windows/scripts/build.cmd b/build_scripts/windows/scripts/build.cmd
index 3944e96b925..94414ed694b 100644
--- a/build_scripts/windows/scripts/build.cmd
+++ b/build_scripts/windows/scripts/build.cmd
@@ -13,10 +13,22 @@ if "%CLI_VERSION%"=="" (
     echo Please set the CLI_VERSION environment variable, e.g. 2.0.13
     goto ERROR
 )
+
+if "%ARCH%"=="" (
+    set ARCH=x86
+)
+if "%ARCH%"=="x86" (
+    set PYTHON_ARCH=win32
+) else if "%ARCH%"=="x64" (
+    set PYTHON_ARCH=amd64
+) else (
+    echo Please set ARCH to "x86" or "x64"
+    goto ERROR
+)
 set PYTHON_VERSION=3.10.10
 
 set WIX_DOWNLOAD_URL="https://azurecliprod.blob.core.windows.net/msi/wix310-binaries-mirror.zip"
-set PYTHON_DOWNLOAD_URL="https://www.python.org/ftp/python/%PYTHON_VERSION%/python-%PYTHON_VERSION%-embed-win32.zip"
+set PYTHON_DOWNLOAD_URL="https://www.python.org/ftp/python/%PYTHON_VERSION%/python-%PYTHON_VERSION%-embed-%PYTHON_ARCH%.zip"
 
 REM https://pip.pypa.io/en/stable/installation/#get-pip-py
 set GET_PIP_DOWNLOAD_URL="https://bootstrap.pypa.io/get-pip.py"
@@ -34,7 +46,10 @@ set BUILDING_DIR=%ARTIFACTS_DIR%\cli
 set WIX_DIR=%ARTIFACTS_DIR%\wix
 set PYTHON_DIR=%ARTIFACTS_DIR%\Python
 
-set REPO_ROOT=%~dp0..\..\..
+REM Get the absolute directory since we pushd into different levels of subdirectories.
+PUSHD %~dp0..\..\..
+SET REPO_ROOT=%CD%
+POPD
 
 REM reset working folders
 if exist %BUILDING_DIR% rmdir /s /q %BUILDING_DIR%
@@ -181,7 +196,7 @@ popd
 if %errorlevel% neq 0 goto ERROR
 
 echo Building MSI...
-msbuild /t:rebuild /p:Configuration=Release %REPO_ROOT%\build_scripts\windows\azure-cli.wixproj
+msbuild /t:rebuild /p:Configuration=Release /p:Platform=%ARCH% %REPO_ROOT%\build_scripts\windows\azure-cli.wixproj
 
 if %errorlevel% neq 0 goto ERROR