diff --git a/Misc/NEWS b/Misc/NEWS
index d3ef4d34ec6..e503547e643 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -162,6 +162,11 @@ Build
 - Issue #25825: Update references to the $(LIBPL) installation path on AIX.
   This path was changed in 3.2a4.
 
+Windows
+-------
+
+- Issue #27756: Adds new icons for Python files and processes on Windows.
+  Designs by Cherry Wang.
 
 What's New in Python 3.6.0 alpha 4
 ==================================
diff --git a/PC/icons/launcher.icns b/PC/icons/launcher.icns
new file mode 100644
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diff --git a/PC/icons/launcher.ico b/PC/icons/launcher.ico
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index 00000000000..c4e3c693dcb
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diff --git a/PC/icons/launcher.svg b/PC/icons/launcher.svg
new file mode 100644
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--- /dev/null
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diff --git a/PC/icons/py.icns b/PC/icons/py.icns
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diff --git a/PC/icons/py.ico b/PC/icons/py.ico
new file mode 100644
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diff --git a/PC/icons/py.svg b/PC/icons/py.svg
new file mode 100644
index 00000000000..0924e83fbc7
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+++ b/PC/icons/py.svg
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diff --git a/PC/icons/pyc.icns b/PC/icons/pyc.icns
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diff --git a/PC/icons/pyc.ico b/PC/icons/pyc.ico
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diff --git a/PC/icons/pyc.svg b/PC/icons/pyc.svg
new file mode 100644
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--- /dev/null
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diff --git a/PC/icons/pyd.icns b/PC/icons/pyd.icns
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+++ b/PC/icons/setup.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 32 32"><style>.icon-canvas-transparent{opacity:0;fill:#f6f6f6}.icon-visualstudio-online{fill:#007acc}.icon-disabled-grey{fill:#848484}.icon-white{fill:#fff}.st0{fill:#f0eff1}.st1{fill:#424242}.st2{fill:url(#path1948_1_)}.st3{fill:url(#path1950_1_)}</style><path class="icon-canvas-transparent" d="M32 32H0V0h32v32z" id="canvas"/><g id="iconBg"><path class="st0" d="M18 8v10H1V8h17zm-1.191 15.572a1.004 1.004 0 0 0-.903-.572H2.907c-.385 0-.74.225-.903.572L.886 25.928A.748.748 0 0 0 1.563 27H17.25a.748.748 0 0 0 .677-1.072l-1.118-2.356z"/><path class="icon-disabled-grey" d="M17.927 25.929l-1.118-2.356a1.003 1.003 0 0 0-.903-.573H2.907c-.385 0-.74.225-.903.572L.886 25.928A.748.748 0 0 0 1.563 27H17.25a.747.747 0 0 0 .633-.349.746.746 0 0 0 .044-.722zM1.959 26l.949-2h12.998l.949 2H1.959zM6 22v-1h3v-2h1v2h3v1H6z"/><path class="st1" d="M0 7v12h19V7H0zm18 11H1V8h17v10z"/></g><g id="iconFg"><path class="icon-white" d="M12 6V0H7v6H2.755L9.5 13.495 16.245 6z"/><path class="icon-visualstudio-online" d="M8 4h3v3h3l-4.5 5L5 7h3V4zm3-2H8v1h3V2zm0-2H8v1h3V0z"/></g><g id="colorImportance"><path class="icon-white" d="M31.596 24.063C31.246 25.116 30.595 27 28.349 27H27v1.313c0 .905-.368 2.537-2.997 3.298-.903.261-1.727.389-2.565.389-.83 0-1.597-.128-2.493-.392C17.029 31.045 16 29.844 16 28.313V27h-1.296c-1.698 0-2.944-1.141-3.417-3.11-.469-1.944-.469-3.02 0-4.967.451-1.881 1.961-2.923 3.845-2.923H16v-1.697c0-2.005.834-2.845 3.054-3.238.728-.128 1.474-.065 2.296-.065h.003c.921 0 1.735-.07 2.537.064 1.816.303 3.11 1.585 3.11 3.24V16h1.349c1.142 0 2.636.356 3.27 2.912.515 2.072.509 3.559-.023 5.151z"/><linearGradient id="path1948_1_" gradientUnits="userSpaceOnUse" x1="522.205" y1="-288.668" x2="540.902" y2="-304.754" gradientTransform="matrix(.5625 0 0 -.568 -282.272 -151.69)"><stop offset="0" stop-color="#5a9fd4"/><stop offset="1" stop-color="#306998"/></linearGradient><path id="path1948_9_" class="st2" d="M21.354 11.725c-.786.004-1.537.071-2.197.188-1.946.344-2.299 1.063-2.299 2.39v1.753h4.598v.584h-6.324c-1.336 0-2.507.803-2.873 2.331-.422 1.751-.441 2.844 0 4.673.327 1.361 1.108 2.331 2.444 2.331h1.581v-2.101c0-1.518 1.313-2.857 2.873-2.857h4.593c1.279 0 2.299-1.053 2.299-2.337v-4.379c0-1.246-1.051-2.182-2.299-2.39-.79-.13-1.61-.189-2.396-.186zm-2.486 1.41c.475 0 .863.394.863.879a.87.87 0 0 1-.863.874.868.868 0 0 1-.863-.874c0-.485.386-.879.863-.879z"/><linearGradient id="path1950_1_" gradientUnits="userSpaceOnUse" x1="548.13" y1="-314.489" x2="541.454" y2="-305.043" gradientTransform="matrix(.5625 0 0 -.568 -282.272 -151.69)"><stop offset="0" stop-color="#ffd43b"/><stop offset="1" stop-color="#ffe873"/></linearGradient><path id="path1950_9_" class="st3" d="M26.623 16.64v2.042c0 1.583-1.342 2.915-2.873 2.915h-4.593c-1.258 0-2.299 1.077-2.299 2.337v4.379c0 1.246 1.084 1.979 2.299 2.337 1.456.428 2.851.505 4.593 0 1.158-.335 2.299-1.01 2.299-2.337V26.56h-4.593v-.584H28.348c1.336 0 1.834-.932 2.299-2.331.48-1.44.46-2.826 0-4.673-.33-1.33-.961-2.331-2.299-2.331h-1.725zm-2.584 11.089c.477 0 .863.391.863.874a.871.871 0 0 1-.863.879.872.872 0 0 1-.863-.879.87.87 0 0 1 .863-.874z"/></g></svg>
\ No newline at end of file
diff --git a/PC/launcher.ico b/PC/launcher.ico
deleted file mode 100644
index dad7d572ce7..00000000000
Binary files a/PC/launcher.ico and /dev/null differ
diff --git a/PC/py.ico b/PC/py.ico
deleted file mode 100644
index 3357aef1488..00000000000
Binary files a/PC/py.ico and /dev/null differ
diff --git a/PC/pyc.ico b/PC/pyc.ico
deleted file mode 100644
index f7bd2b1cc23..00000000000
Binary files a/PC/pyc.ico and /dev/null differ
diff --git a/PC/pycon.ico b/PC/pycon.ico
deleted file mode 100644
index 1ab629eff26..00000000000
Binary files a/PC/pycon.ico and /dev/null differ
diff --git a/PC/pylauncher.rc b/PC/pylauncher.rc
index a8db0a842f8..3da3445f5fc 100644
--- a/PC/pylauncher.rc
+++ b/PC/pylauncher.rc
@@ -7,9 +7,13 @@
 #include <winuser.h>
 1 RT_MANIFEST "python.manifest"
 
-1 ICON DISCARDABLE "launcher.ico" 
-2 ICON DISCARDABLE "py.ico" 
-3 ICON DISCARDABLE "pyc.ico" 
+1 ICON DISCARDABLE "icons\launcher.ico" 
+2 ICON DISCARDABLE "icons\py.ico" 
+3 ICON DISCARDABLE "icons\pyc.ico" 
+4 ICON DISCARDABLE "icons\pyd.ico" 
+5 ICON DISCARDABLE "icons\python.ico"
+6 ICON DISCARDABLE "icons\pythonw.ico"
+7 ICON DISCARDABLE "icons\setup.ico" 
 
 /////////////////////////////////////////////////////////////////////////////
 //
diff --git a/PC/python_exe.rc b/PC/python_exe.rc
index 91785a1e064..ae0b029b807 100644
--- a/PC/python_exe.rc
+++ b/PC/python_exe.rc
@@ -7,7 +7,7 @@
 #include <winuser.h>
 1 RT_MANIFEST "python.manifest"
 
-1 ICON DISCARDABLE "pycon.ico" 
+1 ICON DISCARDABLE "icons\python.ico" 
 
 
 /////////////////////////////////////////////////////////////////////////////
diff --git a/PC/pythonw_exe.rc b/PC/pythonw_exe.rc
new file mode 100644
index 00000000000..88bf3592e18
--- /dev/null
+++ b/PC/pythonw_exe.rc
@@ -0,0 +1,49 @@
+// Resource script for Python console EXEs.
+
+#include "python_ver_rc.h"
+
+// Include the manifest file that indicates we support all
+// current versions of Windows.
+#include <winuser.h>
+1 RT_MANIFEST "python.manifest"
+
+1 ICON DISCARDABLE "icons\pythonw.ico" 
+
+
+/////////////////////////////////////////////////////////////////////////////
+//
+// Version
+//
+
+VS_VERSION_INFO VERSIONINFO
+ FILEVERSION PYVERSION64
+ PRODUCTVERSION PYVERSION64
+ FILEFLAGSMASK 0x3fL
+#ifdef _DEBUG
+ FILEFLAGS VS_FF_DEBUG
+#else
+ FILEFLAGS 0x0L
+#endif
+ FILEOS VOS__WINDOWS32
+ FILETYPE VFT_APP
+ FILESUBTYPE 0x0L
+BEGIN
+    BLOCK "StringFileInfo"
+    BEGIN
+        BLOCK "000004b0"
+        BEGIN
+            VALUE "CompanyName", PYTHON_COMPANY "\0"
+            VALUE "FileDescription", "Python\0"
+            VALUE "FileVersion", PYTHON_VERSION
+            VALUE "InternalName", "Python Application\0"
+            VALUE "LegalCopyright", PYTHON_COPYRIGHT "\0"
+            VALUE "OriginalFilename", "pythonw" PYTHON_DEBUG_EXT ".exe\0"
+            VALUE "ProductName", "Python\0"
+            VALUE "ProductVersion", PYTHON_VERSION
+        END
+    END
+    BLOCK "VarFileInfo"
+    BEGIN
+        VALUE "Translation", 0x0, 1200
+    END
+END
diff --git a/PCbuild/pythonw.vcxproj b/PCbuild/pythonw.vcxproj
index caed1e8dcfa..e40f66c856b 100644
--- a/PCbuild/pythonw.vcxproj
+++ b/PCbuild/pythonw.vcxproj
@@ -62,7 +62,7 @@
     </Link>
   </ItemDefinitionGroup>
   <ItemGroup>
-    <ResourceCompile Include="..\PC\python_exe.rc" />
+    <ResourceCompile Include="..\PC\pythonw_exe.rc" />
   </ItemGroup>
   <ItemGroup>
     <ClCompile Include="..\PC\WinMain.c" />
diff --git a/Tools/msi/bundle/bundle.ico b/Tools/msi/bundle/bundle.ico
deleted file mode 100644
index 1ab629eff26..00000000000
Binary files a/Tools/msi/bundle/bundle.ico and /dev/null differ
diff --git a/Tools/msi/bundle/bundle.wxs b/Tools/msi/bundle/bundle.wxs
index 38307e063cb..c89e6ee4c7d 100644
--- a/Tools/msi/bundle/bundle.wxs
+++ b/Tools/msi/bundle/bundle.wxs
@@ -4,7 +4,7 @@
   <Bundle Name="!(loc.FullProductName)"
           UpgradeCode="$(var.CoreUpgradeCode)"
           Version="$(var.Version)"
-          IconSourceFile="bundle.ico"
+          IconSourceFile="..\..\..\PC\icons\setup.ico"
           Manufacturer="!(loc.Manufacturer)"
           AboutUrl="http://www.python.org/"
           DisableModify="button"
diff --git a/Tools/msi/common.wxs b/Tools/msi/common.wxs
index dd41ce88fbb..a97ee92f9f8 100644
--- a/Tools/msi/common.wxs
+++ b/Tools/msi/common.wxs
@@ -44,7 +44,7 @@
     
     <Fragment>
         <!-- Include an icon for the Programs and Features dialog -->
-        <Icon Id="ARPIcon" SourceFile="!(bindpath.src)PC\pycon.ico" />
+        <Icon Id="ARPIcon" SourceFile="!(bindpath.src)PC\icons\setup.ico" />
         <Property Id="ARPPRODUCTICON" Value="ARPIcon" />
         <Property Id="ARPNOMODIFY" Value="1" />
         <Property Id="DISABLEADVTSHORTCUTS" Value="1" />
diff --git a/Tools/msi/exe/exe_files.wxs b/Tools/msi/exe/exe_files.wxs
index c157f40d329..01385874fa9 100644
--- a/Tools/msi/exe/exe_files.wxs
+++ b/Tools/msi/exe/exe_files.wxs
@@ -69,10 +69,13 @@
     <Fragment>
         <ComponentGroup Id="exe_icons">
             <Component Id="py.ico" Directory="DLLs" Guid="*">
-                <File Name="py.ico" Source="!(bindpath.src)PC\py.ico" KeyPath="yes" />
+                <File Name="py.ico" Source="!(bindpath.src)PC\icons\py.ico" KeyPath="yes" />
             </Component>
             <Component Id="pyc.ico" Directory="DLLs" Guid="*">
-                <File Name="pyc.ico" Source="!(bindpath.src)PC\pyc.ico" KeyPath="yes" />
+                <File Name="pyc.ico" Source="!(bindpath.src)PC\icons\pyc.ico" KeyPath="yes" />
+            </Component>
+            <Component Id="pyd.ico" Directory="DLLs" Guid="*">
+                <File Name="pyd.ico" Source="!(bindpath.src)PC\icons\pyd.ico" KeyPath="yes" />
             </Component>
         </ComponentGroup>
     </Fragment>
diff --git a/Tools/msi/launcher/launcher_en-US.wxl b/Tools/msi/launcher/launcher_en-US.wxl
index e4c1aaa9fa2..a7e3827c528 100644
--- a/Tools/msi/launcher/launcher_en-US.wxl
+++ b/Tools/msi/launcher/launcher_en-US.wxl
@@ -11,6 +11,7 @@
     <String Id="PythonFileDescription">Python File</String>
     <String Id="PythonNoConFileDescription">Python File (no console)</String>
     <String Id="PythonCompiledFileDescription">Compiled Python File</String>
+    <String Id="PythonExtensionDescription">Python Extension Module</String>
     <String Id="PythonArchiveFileDescription">Python Zip Application File</String>
     <String Id="PythonNoConArchiveFileDescription">Python Zip Application File (no console)</String>
 </WixLocalization>
diff --git a/Tools/msi/launcher/launcher_reg.wxs b/Tools/msi/launcher/launcher_reg.wxs
index 981961ab0d8..dace97ee58b 100644
--- a/Tools/msi/launcher/launcher_reg.wxs
+++ b/Tools/msi/launcher/launcher_reg.wxs
@@ -27,14 +27,18 @@
                 </ProgId>
                 <RegistryValue Root="HKCR" Key="Python.CompiledFile\shellex\DropHandler" Value="{BEA218D2-6950-497B-9434-61683EC065FE}" Type="string" />
 
-                <ProgId Id="Python.ArchiveFile" Description="!(loc.PythonArchiveFileDescription)" Advertise="no" Icon="py.exe" IconIndex="1">
+                <ProgId Id="Python.Extension" Description="!(loc.PythonExtensionDescription)" Advertise="no" Icon="py.exe" IconIndex="3">
+                    <Extension Id="pyd" />
+                </ProgId>
+
+                <ProgId Id="Python.ArchiveFile" Description="!(loc.PythonArchiveFileDescription)" Advertise="no" Icon="py.exe" IconIndex="5">
                     <Extension Id="pyz" ContentType="application/x-zip-compressed">
                         <Verb Id="open" TargetFile="py.exe" Argument="&quot;%L&quot; %*" />
                     </Extension>
                 </ProgId>
                 <RegistryValue Root="HKCR" Key="Python.ArchiveFile\shellex\DropHandler" Value="{BEA218D2-6950-497B-9434-61683EC065FE}" Type="string" />
                 
-                <ProgId Id="Python.NoConArchiveFile" Description="!(loc.PythonNoConArchiveFileDescription)" Advertise="no" Icon="py.exe" IconIndex="1">
+                <ProgId Id="Python.NoConArchiveFile" Description="!(loc.PythonNoConArchiveFileDescription)" Advertise="no" Icon="py.exe" IconIndex="5">
                     <Extension Id="pyzw" ContentType="application/x-zip-compressed">
                         <Verb Id="open" TargetFile="pyw.exe" Argument="&quot;%L&quot; %*" />
                     </Extension>