diff --git a/.azure-pipelines/windows-release/stage-pack-msix.yml b/.azure-pipelines/windows-release/stage-pack-msix.yml
index 26a5712e845ca9..f967cfdbe326f8 100644
--- a/.azure-pipelines/windows-release/stage-pack-msix.yml
+++ b/.azure-pipelines/windows-release/stage-pack-msix.yml
@@ -120,10 +120,11 @@ jobs:
       artifactName: unsigned_msix
       downloadPath: $(Build.BinariesDirectory)
 
+  # MSIX must be signed and timestamped simultaneously
   - powershell: |
       $failed = $true
       foreach ($retry in 1..3) {
-          signtool sign /a /n "$(SigningCertificate)" /fd sha256 /t http://timestamp.verisign.com/scripts/timestamp.dll /d "$(SigningDescription)" (gi *.msix)
+          signtool sign /a /n "$(SigningCertificate)" /fd sha256 /tr http://timestamp.digicert.com/ /td sha256 /d "$(SigningDescription)" (gi *.msix)
           if ($?) {
               $failed = $false
               break
diff --git a/.azure-pipelines/windows-release/stage-pack-nuget.yml b/.azure-pipelines/windows-release/stage-pack-nuget.yml
index b100364820d95b..8dfea382c35622 100644
--- a/.azure-pipelines/windows-release/stage-pack-nuget.yml
+++ b/.azure-pipelines/windows-release/stage-pack-nuget.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), eq(variables['DoNuget'], 'true'))
 
   pool:
-    vmImage: windows-2019
+    name: 'Windows Release'
 
   workspace:
     clean: all
@@ -36,6 +36,14 @@ jobs:
       nuget pack "$(Build.BinariesDirectory)\layout\python.nuspec" -OutputDirectory $(Build.ArtifactStagingDirectory) -NoPackageAnalysis -NonInteractive
     displayName: 'Create nuget package'
 
+  - powershell: |
+      gci *.nupkg | %{
+        nuget sign "$_" -CertificateSubjectName "$(SigningCertificate)" -Timestamper http://timestamp.digicert.com/ -Overwrite
+      }
+    displayName: 'Sign nuget package'
+    workingDirectory: $(Build.ArtifactStagingDirectory)
+    condition: and(succeeded(), variables['SigningCertificate'])
+
   - task: PublishBuildArtifacts@1
     displayName: 'Publish Artifact: nuget'
     inputs:
diff --git a/.azure-pipelines/windows-release/stage-sign.yml b/.azure-pipelines/windows-release/stage-sign.yml
index 584772af8b428e..c21e1c9f2b0f9b 100644
--- a/.azure-pipelines/windows-release/stage-sign.yml
+++ b/.azure-pipelines/windows-release/stage-sign.yml
@@ -57,7 +57,7 @@ jobs:
       $files = (gi ${{ parameters.Include }} -Exclude ${{ parameters.Exclude }})
       $failed = $true
       foreach ($retry in 1..10) {
-          signtool timestamp /t http://timestamp.verisign.com/scripts/timestamp.dll $files
+          signtool timestamp /tr http://timestamp.digicert.com/ /td sha256 $files
           if ($?) {
               $failed = $false
               break
diff --git a/PCbuild/pyproject.props b/PCbuild/pyproject.props
index c659d14ff8dc93..d7762ca1bc685f 100644
--- a/PCbuild/pyproject.props
+++ b/PCbuild/pyproject.props
@@ -176,8 +176,8 @@ public override bool Execute() {
     <SdkBinPath Condition="!Exists($(SdkBinPath))">$(registry:HKEY_LOCAL_MACHINE\Software\Microsoft\Windows Kits\Installed Roots@KitsRoot81)\bin\x86</SdkBinPath>
     <SdkBinPath Condition="!Exists($(SdkBinPath))">$(registry:HKEY_LOCAL_MACHINE\Software\Microsoft\Windows Kits\Installed Roots@KitsRoot)\bin\x86</SdkBinPath>
     <SdkBinPath Condition="!Exists($(SdkBinPath))">$(registry:HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Microsoft SDKs\Windows\v7.1A@InstallationFolder)\Bin\</SdkBinPath>
-    <_SignCommand Condition="Exists($(SdkBinPath)) and '$(SigningCertificate)' != '' and $(SupportSigning)">"$(SdkBinPath)\signtool.exe" sign /a /n "$(SigningCertificate)" /fd sha256 /t http://timestamp.verisign.com/scripts/timestamp.dll /d "Python $(PythonVersion)"</_SignCommand>
-    <_SignCommand Condition="Exists($(SdkBinPath)) and '$(SigningCertificateSha1)' != '' and $(SupportSigning)">"$(SdkBinPath)\signtool.exe" sign /a /sha1 "$(SigningCertificateSha1)" /fd sha256 /t http://timestamp.verisign.com/scripts/timestamp.dll /d "Python $(PythonVersion)"</_SignCommand>
+    <_SignCommand Condition="Exists($(SdkBinPath)) and '$(SigningCertificate)' != '' and $(SupportSigning)">"$(SdkBinPath)\signtool.exe" sign /a /n "$(SigningCertificate)" /fd sha256 /tr http://timestamp.digicert.com/ /td sha256 /d "Python $(PythonVersion)"</_SignCommand>
+    <_SignCommand Condition="Exists($(SdkBinPath)) and '$(SigningCertificateSha1)' != '' and $(SupportSigning)">"$(SdkBinPath)\signtool.exe" sign /a /sha1 "$(SigningCertificateSha1)" /fd sha256 /tr http://timestamp.digicert.com/ /td sha256 /d "Python $(PythonVersion)"</_SignCommand>
     <_MakeCatCommand Condition="Exists($(SdkBinPath))">"$(SdkBinPath)\makecat.exe"</_MakeCatCommand>
   </PropertyGroup>
 
diff --git a/Tools/msi/sdktools.psm1 b/Tools/msi/sdktools.psm1
index 8081b104d85a7f..c5973f9abc6abf 100644
--- a/Tools/msi/sdktools.psm1
+++ b/Tools/msi/sdktools.psm1
@@ -37,11 +37,11 @@ function Sign-File {
 
     foreach ($a in $files) {
         if ($certsha1) {
-            SignTool sign /sha1 $certsha1 /fd sha256 /t http://timestamp.verisign.com/scripts/timestamp.dll /d $description $a
+            SignTool sign /sha1 $certsha1 /fd sha256 /tr http://timestamp.digicert.com/ /td sha256 /d $description $a
         } elseif ($certname) {
-            SignTool sign /a /n $certname /fd sha256 /t http://timestamp.verisign.com/scripts/timestamp.dll /d $description $a
+            SignTool sign /a /n $certname /fd sha256 /tr http://timestamp.digicert.com/ /td sha256 /d $description $a
         } elseif ($certfile) {
-            SignTool sign /f $certfile /fd sha256 /t http://timestamp.verisign.com/scripts/timestamp.dll /d $description $a
+            SignTool sign /f $certfile /fd sha256 /tr http://timestamp.digicert.com/ /td sha256 /d $description $a
         }
     }
 }