diff --git a/.azure-pipelines/ci.yml b/.azure-pipelines/ci.yml
index 9b638ddd004..50dc50a6549 100644
--- a/.azure-pipelines/ci.yml
+++ b/.azure-pipelines/ci.yml
@@ -61,7 +61,7 @@ jobs:
   variables:
     testRunTitle: '$(build.sourceBranchName)-linux'
     testRunPlatform: linux
-    openssl_version: 1.1.1f
+    openssl_version: 1.1.1g
 
   steps:
   - template: ./posix-steps.yml
@@ -118,7 +118,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.1f
+    openssl_version: 1.1.1g
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.azure-pipelines/pr.yml b/.azure-pipelines/pr.yml
index 65f23eb62ee..228f9db4f8e 100644
--- a/.azure-pipelines/pr.yml
+++ b/.azure-pipelines/pr.yml
@@ -61,7 +61,7 @@ jobs:
   variables:
     testRunTitle: '$(system.pullRequest.TargetBranch)-linux'
     testRunPlatform: linux
-    openssl_version: 1.1.1f
+    openssl_version: 1.1.1g
 
   steps:
   - template: ./posix-steps.yml
@@ -118,7 +118,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.1f
+    openssl_version: 1.1.1g
 
   steps:
   - template: ./posix-steps.yml
diff --git a/Misc/NEWS.d/next/Windows/2020-06-12-13-13-44.bpo-40164.SPrSn5.rst b/Misc/NEWS.d/next/Windows/2020-06-12-13-13-44.bpo-40164.SPrSn5.rst
new file mode 100644
index 00000000000..6390de717d7
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2020-06-12-13-13-44.bpo-40164.SPrSn5.rst
@@ -0,0 +1 @@
+Updates Windows OpenSSL to 1.1.1g
\ No newline at end of file
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index fa27cdf369d..4171fd740c7 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -53,7 +53,7 @@ echo.Fetching external libraries...
 set libraries=
 set libraries=%libraries%                                       bzip2-1.0.6
 if NOT "%IncludeLibffiSrc%"=="false" set libraries=%libraries%  libffi
-if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1f
+if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1g
 set libraries=%libraries%                                       sqlite-3.31.1.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tcl-core-8.6.9.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tk-8.6.9.0
@@ -77,7 +77,7 @@ echo.Fetching external binaries...
 
 set binaries=
 if NOT "%IncludeLibffi%"=="false"  set binaries=%binaries% libffi
-if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1f
+if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1g
 if NOT "%IncludeTkinter%"=="false" set binaries=%binaries% tcltk-8.6.9.0
 if NOT "%IncludeSSLSrc%"=="false"  set binaries=%binaries% nasm-2.11.06
 
diff --git a/PCbuild/python.props b/PCbuild/python.props
index d1d16d61be8..6388d1b6426 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -62,8 +62,8 @@
     <libffiDir>$(ExternalsDir)libffi\</libffiDir>
     <libffiOutDir>$(ExternalsDir)libffi\$(ArchName)\</libffiOutDir>
     <libffiIncludeDir>$(libffiOutDir)include</libffiIncludeDir>
-    <opensslDir>$(ExternalsDir)openssl-1.1.1f\</opensslDir>
-    <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1f\$(ArchName)\</opensslOutDir>
+    <opensslDir>$(ExternalsDir)openssl-1.1.1g\</opensslDir>
+    <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1g\$(ArchName)\</opensslOutDir>
     <opensslIncludeDir>$(opensslOutDir)include</opensslIncludeDir>
     <nasmDir>$(ExternalsDir)\nasm-2.11.06\</nasmDir>
     <zlibDir>$(ExternalsDir)\zlib-1.2.11\</zlibDir>