diff --git a/Misc/NEWS.d/next/Windows/2020-05-01-20-57-57.bpo-40458.Eb0ueI.rst b/Misc/NEWS.d/next/Windows/2020-05-01-20-57-57.bpo-40458.Eb0ueI.rst
new file mode 100644
index 00000000000..4dc1ff480df
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2020-05-01-20-57-57.bpo-40458.Eb0ueI.rst
@@ -0,0 +1 @@
+Increase reserved stack space to prevent overflow crash on Windows.
diff --git a/PCbuild/python_uwp.vcxproj b/PCbuild/python_uwp.vcxproj
index 5ff120a0da3..fb27e9e7122 100644
--- a/PCbuild/python_uwp.vcxproj
+++ b/PCbuild/python_uwp.vcxproj
@@ -95,6 +95,7 @@
     <Link>
       <AdditionalDependencies>windowsapp.lib;%(AdditionalDependencies)</AdditionalDependencies>
       <SubSystem>Console</SubSystem>
+      <StackReserveSize>2000000</StackReserveSize>
     </Link>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="$(Configuration) != 'Debug'">
diff --git a/PCbuild/pythonw_uwp.vcxproj b/PCbuild/pythonw_uwp.vcxproj
index 828d0d1ccac..e21e46a1b72 100644
--- a/PCbuild/pythonw_uwp.vcxproj
+++ b/PCbuild/pythonw_uwp.vcxproj
@@ -95,6 +95,7 @@
     <Link>
       <AdditionalDependencies>windowsapp.lib;%(AdditionalDependencies)</AdditionalDependencies>
       <SubSystem>Windows</SubSystem>
+      <StackReserveSize>2000000</StackReserveSize>
     </Link>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="$(Configuration) != 'Debug'">