diff --git a/.azure-pipelines/windows-release/stage-build.yml b/.azure-pipelines/windows-release/stage-build.yml
index 9391a91e30b5e6..69f3b1e16451ec 100644
--- a/.azure-pipelines/windows-release/stage-build.yml
+++ b/.azure-pipelines/windows-release/stage-build.yml
@@ -3,7 +3,7 @@ jobs:
   displayName: Docs build
   pool:
     name: 'Windows Release'
-    #vmName: win2016-vs2017
+    #vmImage: windows-2019
 
   workspace:
     clean: all
@@ -45,7 +45,7 @@ jobs:
   displayName: Python build
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
@@ -91,7 +91,7 @@ jobs:
   condition: and(succeeded(), ne(variables['DoPGO'], 'true'))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
@@ -141,7 +141,7 @@ jobs:
   displayName: Publish Tcl/Tk Library
 
   pool:
-    vmName: windows-latest
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-layout-embed.yml b/.azure-pipelines/windows-release/stage-layout-embed.yml
index 3306e1cbc49d98..dbccdead143b21 100644
--- a/.azure-pipelines/windows-release/stage-layout-embed.yml
+++ b/.azure-pipelines/windows-release/stage-layout-embed.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), eq(variables['DoEmbed'], 'true'))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-layout-full.yml b/.azure-pipelines/windows-release/stage-layout-full.yml
index 78bc1b3975e93d..8fc8da3e52fe03 100644
--- a/.azure-pipelines/windows-release/stage-layout-full.yml
+++ b/.azure-pipelines/windows-release/stage-layout-full.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), eq(variables['DoLayout'], 'true'))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-layout-msix.yml b/.azure-pipelines/windows-release/stage-layout-msix.yml
index 60a5c9ea5435c8..def4f7d3c6bee5 100644
--- a/.azure-pipelines/windows-release/stage-layout-msix.yml
+++ b/.azure-pipelines/windows-release/stage-layout-msix.yml
@@ -3,7 +3,7 @@ jobs:
   displayName: Make MSIX layout
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-layout-nuget.yml b/.azure-pipelines/windows-release/stage-layout-nuget.yml
index 7e20f89530349c..41cdff850e83be 100644
--- a/.azure-pipelines/windows-release/stage-layout-nuget.yml
+++ b/.azure-pipelines/windows-release/stage-layout-nuget.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), eq(variables['DoNuget'], 'true'))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-msi.yml b/.azure-pipelines/windows-release/stage-msi.yml
index 7afc816a0c6e9c..9b965b09c14748 100644
--- a/.azure-pipelines/windows-release/stage-msi.yml
+++ b/.azure-pipelines/windows-release/stage-msi.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), not(variables['SigningCertificate']))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   variables:
     ReleaseUri: http://www.python.org/{arch}
diff --git a/.azure-pipelines/windows-release/stage-pack-msix.yml b/.azure-pipelines/windows-release/stage-pack-msix.yml
index f17ba9628e21b0..07e343a0b4e0c7 100644
--- a/.azure-pipelines/windows-release/stage-pack-msix.yml
+++ b/.azure-pipelines/windows-release/stage-pack-msix.yml
@@ -3,7 +3,7 @@ jobs:
   displayName: Pack MSIX bundles
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-pack-nuget.yml b/.azure-pipelines/windows-release/stage-pack-nuget.yml
index 34619fc5fdc318..b100364820d95b 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:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-publish-nugetorg.yml b/.azure-pipelines/windows-release/stage-publish-nugetorg.yml
index b78bd493a0fd1b..d5edf44ef5c2ec 100644
--- a/.azure-pipelines/windows-release/stage-publish-nugetorg.yml
+++ b/.azure-pipelines/windows-release/stage-publish-nugetorg.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), eq(variables['DoNuget'], 'true'))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-publish-pythonorg.yml b/.azure-pipelines/windows-release/stage-publish-pythonorg.yml
index 8c95f1b950cd75..b4710d8c248e23 100644
--- a/.azure-pipelines/windows-release/stage-publish-pythonorg.yml
+++ b/.azure-pipelines/windows-release/stage-publish-pythonorg.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), and(eq(variables['DoMSI'], 'true'), eq(variables['DoEmbed'], 'true')))
 
   pool:
-    #vmName: win2016-vs2017
+    #vmImage: windows-2019
     name: 'Windows Release'
 
   workspace:
diff --git a/.azure-pipelines/windows-release/stage-publish-store.yml b/.azure-pipelines/windows-release/stage-publish-store.yml
index b22147b1ab45e7..e0512b95f27da8 100644
--- a/.azure-pipelines/windows-release/stage-publish-store.yml
+++ b/.azure-pipelines/windows-release/stage-publish-store.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), eq(variables['DoMSIX'], 'true'))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-sign.yml b/.azure-pipelines/windows-release/stage-sign.yml
index a0adc0581229d9..4d757ae8fca032 100644
--- a/.azure-pipelines/windows-release/stage-sign.yml
+++ b/.azure-pipelines/windows-release/stage-sign.yml
@@ -114,7 +114,7 @@ jobs:
   condition: and(succeeded(), not(variables['SigningCertificate']))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   steps:
   - checkout: none
diff --git a/.azure-pipelines/windows-release/stage-test-embed.yml b/.azure-pipelines/windows-release/stage-test-embed.yml
index b33176266a20da..d99bd74722bacb 100644
--- a/.azure-pipelines/windows-release/stage-test-embed.yml
+++ b/.azure-pipelines/windows-release/stage-test-embed.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), eq(variables['DoEmbed'], 'true'))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-test-msi.yml b/.azure-pipelines/windows-release/stage-test-msi.yml
index 27b0c96987a7a0..21e38c39590f70 100644
--- a/.azure-pipelines/windows-release/stage-test-msi.yml
+++ b/.azure-pipelines/windows-release/stage-test-msi.yml
@@ -3,7 +3,7 @@ jobs:
   displayName: Test MSI
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/.azure-pipelines/windows-release/stage-test-nuget.yml b/.azure-pipelines/windows-release/stage-test-nuget.yml
index 1f8b601d0d023b..94d815e95226ef 100644
--- a/.azure-pipelines/windows-release/stage-test-nuget.yml
+++ b/.azure-pipelines/windows-release/stage-test-nuget.yml
@@ -4,7 +4,7 @@ jobs:
   condition: and(succeeded(), eq(variables['DoNuget'], 'true'))
 
   pool:
-    vmName: win2016-vs2017
+    vmImage: windows-2019
 
   workspace:
     clean: all
diff --git a/Misc/NEWS.d/next/Windows/2020-02-28-22-46-09.bpo-39789.67XRoP.rst b/Misc/NEWS.d/next/Windows/2020-02-28-22-46-09.bpo-39789.67XRoP.rst
new file mode 100644
index 00000000000000..077b0afcba3c10
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2020-02-28-22-46-09.bpo-39789.67XRoP.rst
@@ -0,0 +1 @@
+Update Windows release build machines to Visual Studio 2019 (MSVC 14.2).
diff --git a/PC/layout/support/nuspec.py b/PC/layout/support/nuspec.py
index 9c6a9a91595098..dbcb713ef9d0c0 100644
--- a/PC/layout/support/nuspec.py
+++ b/PC/layout/support/nuspec.py
@@ -14,7 +14,7 @@
 NUSPEC_DATA = {
     "PYTHON_TAG": VER_DOT,
     "PYTHON_VERSION": os.getenv("PYTHON_NUSPEC_VERSION"),
-    "FILELIST": r'    <file src="**\*" target="tools" />',
+    "FILELIST": r'    <file src="**\*" exclude="python.png" target="tools" />',
     "GIT": sys._git,
 }
 
@@ -31,7 +31,7 @@
         VER_DOT, VER_MICRO, "-" if VER_SUFFIX else "", VER_SUFFIX
     )
 
-FILELIST_WITH_PROPS = r"""    <file src="**\*" exclude="python.props" target="tools" />
+FILELIST_WITH_PROPS = r"""    <file src="**\*" exclude="python.png;python.props" target="tools" />
     <file src="python.props" target="build\native" />"""
 
 NUSPEC_TEMPLATE = r"""<?xml version="1.0"?>
@@ -44,13 +44,13 @@
     <license type="file">tools\LICENSE.txt</license>
     <projectUrl>https://www.python.org/</projectUrl>
     <description>Installs {PYTHON_BITNESS} Python for use in build scenarios.</description>
-    <icon>images\logox128.png</icon>
+    <icon>images\python.png</icon>
     <iconUrl>https://www.python.org/static/favicon.ico</iconUrl>
     <tags>python</tags>
     <repository type="git" url="https://github.com/Python/CPython.git" commit="{GIT[2]}" />
   </metadata>
   <files>
-    <file src="{LOGO}" target="images" />
+    <file src="python.png" target="images" />
 {FILELIST}
   </files>
 </package>
@@ -73,6 +73,6 @@ def get_nuspec_layout(ns):
                 data[k] = v
         if ns.include_all or ns.include_props:
             data["FILELIST"] = FILELIST_WITH_PROPS
-        data["LOGO"] = ns.source / "PC" / "icons" / "logox128.png"
         nuspec = NUSPEC_TEMPLATE.format_map(data)
         yield "python.nuspec", ("python.nuspec", nuspec.encode("utf-8"))
+        yield "python.png", ns.source / "PC" / "icons" / "logox128.png"
diff --git a/Tools/nuget/make_pkg.proj b/Tools/nuget/make_pkg.proj
index b387b8eef5423c..710ef3dcb5c01d 100644
--- a/Tools/nuget/make_pkg.proj
+++ b/Tools/nuget/make_pkg.proj
@@ -33,7 +33,7 @@
         
         <PackageArguments Condition="$(Packages) != ''">"$(IntermediateOutputPath)pkg\pip.exe" -B -m pip install -U $(Packages)</PackageArguments>
         
-        <NugetPackCommand>"$(Nuget)" pack "$(MSBuildThisFileDirectory)\$(OutputName).nuspec" -BasePath "$(IntermediateOutputPath)pkg"</NugetPackCommand>
+        <NugetPackCommand>"$(Nuget)" pack "$(IntermediateOutputPath)pkg\python.nuspec" -BasePath "$(IntermediateOutputPath)pkg"</NugetPackCommand>
         <NugetPackSymbolsCommand Condition="Exists('$(MSBuildThisFileDirectory)\$(OutputName).symbols.nuspec')">"$(Nuget)" pack "$(MSBuildThisFileDirectory)\$(OutputName).symbols.nuspec" -BasePath "$(BuildPath.TrimEnd(`\`))"</NugetPackSymbolsCommand>
         <NugetArguments>$(NugetArguments) -OutputDirectory "$(OutputPath.Trim(`\`))"</NugetArguments>
         <NugetArguments>$(NugetArguments) -Version "$(NuspecVersion)"</NugetArguments>