diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 27e1c1b..02efbf6 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -33,8 +33,13 @@ jobs:
 
   build-and-test-windows:
     #if: false  # Temporarily disable
-    name: Build And Test Windows
-    runs-on: windows-latest
+    name: Build And Test Windows ${{ matrix.os-version }} ${{ matrix.crypto }}
+    runs-on: windows-${{ matrix.os-version }}
+    strategy:
+      fail-fast: false
+      matrix:
+        os-version: [2019, 2022]
+        crypto: [OpenSSL, BCrypt]
     env:
       VCPKG_ROOT: ${{ github.workspace }}/vcpkg
     steps:
@@ -65,7 +70,7 @@ jobs:
         run: |
           mkdir build
           cd build
-          cmake -S .. -G Ninja -DBUILD_TESTS=ON -DBUILD_EXAMPLES=ON -DBUILD_TOOLS=ON -DCMAKE_TOOLCHAIN_FILE=${{env.VCPKG_ROOT}}/scripts/buildsystems/vcpkg.cmake
+          cmake -S .. -G Ninja -DBUILD_TESTS=ON -DBUILD_EXAMPLES=ON -DBUILD_TOOLS=ON -DCMAKE_TOOLCHAIN_FILE=${{env.VCPKG_ROOT}}/scripts/buildsystems/vcpkg.cmake -DUSE_CRYPTO=${{matrix.crypto}}
         shell: cmd
 
       # Mark all directories as safe so checkouts performed in CMakeLists.txt don't cause "unsafe repository" errors.
diff --git a/CMakeLists.txt b/CMakeLists.txt
index 61f3159..d1489cb 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -84,15 +84,17 @@ if (WIN32)
 	string(REPLACE "/EHsc" "" CMAKE_CXX_FLAGS "${CMAKE_CXX_FLAGS}")
 	string(REPLACE "/GR" "" CMAKE_CXX_FLAGS "${CMAKE_CXX_FLAGS}")
 
-	#
-	# Check whether BCrypt can be used with this SDK version
-	#
-	cmake_push_check_state()
-		set(CMAKE_REQUIRED_LIBRARIES bcrypt)
-		check_symbol_exists(BCryptEncrypt windows.h BCRYPT_AVAILABLE)
-	cmake_pop_check_state()
-	if (NOT BCRYPT_AVAILABLE AND USE_CRYPTO STREQUAL "BCrypt")
-		message(FATAL_ERROR "You're on Windows but BCrypt seems to be unavailable, you will need OpenSSL")
+	if (USE_CRYPTO STREQUAL "BCrypt")
+		#
+		# Check whether BCrypt can be used with this SDK version
+		#
+		cmake_push_check_state()
+			set(CMAKE_REQUIRED_LIBRARIES bcrypt)
+			check_symbol_exists(BCryptEncrypt windows.h BCRYPT_AVAILABLE)
+		cmake_pop_check_state()
+		if (NOT BCRYPT_AVAILABLE)
+			message(FATAL_ERROR "You're on Windows but BCrypt seems to be unavailable, you will need OpenSSL")
+		endif()
 	endif()
 endif()