diff --git a/.azure-pipelines/ci.yml b/.azure-pipelines/ci.yml
index 25cc726504b376..d0efa77f93052b 100644
--- a/.azure-pipelines/ci.yml
+++ b/.azure-pipelines/ci.yml
@@ -57,7 +57,7 @@ jobs:
   variables:
     testRunTitle: '$(build.sourceBranchName)-linux'
     testRunPlatform: linux
-    openssl_version: 1.1.1m
+    openssl_version: 1.1.1n
 
   steps:
   - template: ./posix-steps.yml
@@ -83,7 +83,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.1m
+    openssl_version: 1.1.1n
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.azure-pipelines/pr.yml b/.azure-pipelines/pr.yml
index e2aae324f211be..a4f32460c7ea02 100644
--- a/.azure-pipelines/pr.yml
+++ b/.azure-pipelines/pr.yml
@@ -57,7 +57,7 @@ jobs:
   variables:
     testRunTitle: '$(system.pullRequest.TargetBranch)-linux'
     testRunPlatform: linux
-    openssl_version: 1.1.1m
+    openssl_version: 1.1.1n
 
   steps:
   - template: ./posix-steps.yml
@@ -83,7 +83,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.1m
+    openssl_version: 1.1.1n
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 6f1b16537f5060..596f4d88e26e9f 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -165,7 +165,7 @@ jobs:
     needs: check_source
     if: needs.check_source.outputs.run_tests == 'true'
     env:
-      OPENSSL_VER: 1.1.1m
+      OPENSSL_VER: 1.1.1n
       PYTHONSTRICTEXTENSIONBUILD: 1
     steps:
     - uses: actions/checkout@v2
@@ -207,7 +207,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        openssl_ver: [1.0.2u, 1.1.0l, 1.1.1m, 3.0.1]
+        openssl_ver: [1.0.2u, 1.1.0l, 1.1.1n, 3.0.2]
     env:
       OPENSSL_VER: ${{ matrix.openssl_ver }}
       MULTISSL_DIR: ${{ github.workspace }}/multissl
diff --git a/Mac/BuildScript/build-installer.py b/Mac/BuildScript/build-installer.py
index 47a01056f2e5c4..9909679e0713a3 100755
--- a/Mac/BuildScript/build-installer.py
+++ b/Mac/BuildScript/build-installer.py
@@ -244,9 +244,9 @@ def library_recipes():
 
     result.extend([
           dict(
-              name="OpenSSL 1.1.1m",
-              url="https://www.openssl.org/source/openssl-1.1.1m.tar.gz",
-              checksum='8ec70f665c145c3103f6e330f538a9db',
+              name="OpenSSL 1.1.1n",
+              url="https://www.openssl.org/source/openssl-1.1.1n.tar.gz",
+              checksum='2aad5635f9bb338bc2c6b7d19cbc9676',
               buildrecipe=build_universal_openssl,
               configure=None,
               install=None,
diff --git a/Misc/NEWS.d/next/Build/2022-03-15-09-28-55.bpo-47024.t7-dcu.rst b/Misc/NEWS.d/next/Build/2022-03-15-09-28-55.bpo-47024.t7-dcu.rst
new file mode 100644
index 00000000000000..1035cbab1ba616
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2022-03-15-09-28-55.bpo-47024.t7-dcu.rst
@@ -0,0 +1 @@
+Update OpenSSL to 1.1.1n for macOS installers and all Windows builds.
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index 462e0db361d098..7129898c6bc62f 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -53,7 +53,7 @@ echo.Fetching external libraries...
 set libraries=
 set libraries=%libraries%                                       bzip2-1.0.8
 if NOT "%IncludeLibffiSrc%"=="false" set libraries=%libraries%  libffi-3.3.0
-if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1m
+if NOT "%IncludeSSLSrc%"=="false" set libraries=%libraries%     openssl-1.1.1n
 set libraries=%libraries%                                       sqlite-3.37.2.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tcl-core-8.6.12.0
 if NOT "%IncludeTkinterSrc%"=="false" set libraries=%libraries% tk-8.6.12.0
@@ -77,7 +77,7 @@ echo.Fetching external binaries...
 
 set binaries=
 if NOT "%IncludeLibffi%"=="false"  set binaries=%binaries% libffi-3.3.0
-if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1m
+if NOT "%IncludeSSL%"=="false"     set binaries=%binaries% openssl-bin-1.1.1n
 if NOT "%IncludeTkinter%"=="false" set binaries=%binaries% tcltk-8.6.12.0
 if NOT "%IncludeSSLSrc%"=="false"  set binaries=%binaries% nasm-2.11.06
 
diff --git a/PCbuild/python.props b/PCbuild/python.props
index eddb65879d3ab4..7a11cfafedf5e7 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -63,8 +63,8 @@
     <libffiDir>$(ExternalsDir)libffi-3.3.0\</libffiDir>
     <libffiOutDir>$(ExternalsDir)libffi-3.3.0\$(ArchName)\</libffiOutDir>
     <libffiIncludeDir>$(libffiOutDir)include</libffiIncludeDir>
-    <opensslDir>$(ExternalsDir)openssl-1.1.1m\</opensslDir>
-    <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1m\$(ArchName)\</opensslOutDir>
+    <opensslDir>$(ExternalsDir)openssl-1.1.1n\</opensslDir>
+    <opensslOutDir>$(ExternalsDir)openssl-bin-1.1.1n\$(ArchName)\</opensslOutDir>
     <opensslIncludeDir>$(opensslOutDir)include</opensslIncludeDir>
     <nasmDir>$(ExternalsDir)\nasm-2.11.06\</nasmDir>
     <zlibDir>$(ExternalsDir)\zlib-1.2.11\</zlibDir>
diff --git a/Tools/ssl/multissltests.py b/Tools/ssl/multissltests.py
index 437efb22914b84..14c4918acc2735 100755
--- a/Tools/ssl/multissltests.py
+++ b/Tools/ssl/multissltests.py
@@ -49,8 +49,8 @@
 ]
 
 OPENSSL_RECENT_VERSIONS = [
-    "1.1.1m",
-    "3.0.1"
+    "1.1.1n",
+    "3.0.2"
 ]
 
 LIBRESSL_OLD_VERSIONS = [