diff --git a/ports/openssl/portfile.cmake b/ports/openssl/portfile.cmake
index 445bce149dce82..82d1b2575d4b4b 100644
--- a/ports/openssl/portfile.cmake
+++ b/ports/openssl/portfile.cmake
@@ -21,5 +21,5 @@ else()
     include("${CMAKE_CURRENT_LIST_DIR}/unix/portfile.cmake")
 endif()
 
-file(INSTALL "${CMAKE_CURRENT_LIST_DIR}/vcpkg-cmake-wrapper.cmake" DESTINATION "${CURRENT_PACKAGES_DIR}/share/${PORT}")
+configure_file("${CMAKE_CURRENT_LIST_DIR}/vcpkg-cmake-wrapper.cmake" "${CURRENT_PACKAGES_DIR}/share/${PORT}/vcpkg-cmake-wrapper.cmake" @ONLY)
 file(INSTALL "${CMAKE_CURRENT_LIST_DIR}/usage" DESTINATION "${CURRENT_PACKAGES_DIR}/share/${PORT}")
diff --git a/ports/openssl/unix/portfile.cmake b/ports/openssl/unix/portfile.cmake
index 912234925079d8..7917b38bebf652 100644
--- a/ports/openssl/unix/portfile.cmake
+++ b/ports/openssl/unix/portfile.cmake
@@ -44,6 +44,4 @@ endforeach()
 file(INSTALL ${RESOLVED_HEADERS} DESTINATION ${CURRENT_PACKAGES_DIR}/include/openssl)
 file(INSTALL ${MASTER_COPY_SOURCE_PATH}/LICENSE DESTINATION ${CURRENT_PACKAGES_DIR}/share/${PORT} RENAME copyright)
 
-if(VCPKG_LIBRARY_LINKAGE STREQUAL "static")
-    file(COPY ${CMAKE_CURRENT_LIST_DIR}/vcpkg-cmake-wrapper.cmake DESTINATION ${CURRENT_PACKAGES_DIR}/share/openssl)
-endif()
+string(COMPARE EQUAL "${VCPKG_LIBRARY_LINKAGE}" "static" OPENSSL_USE_UNIX_CMAKE_WRAPPER)
diff --git a/ports/openssl/unix/vcpkg-cmake-wrapper.cmake b/ports/openssl/unix/vcpkg-cmake-wrapper.cmake
deleted file mode 100644
index 43e84cb022a797..00000000000000
--- a/ports/openssl/unix/vcpkg-cmake-wrapper.cmake
+++ /dev/null
@@ -1,18 +0,0 @@
-_find_package(${ARGS})
-if(OPENSSL_FOUND)
-    find_library(OPENSSL_DL_LIBRARY NAMES dl)
-    if(OPENSSL_DL_LIBRARY)
-        list(APPEND OPENSSL_LIBRARIES "dl")
-        if(TARGET OpenSSL::Crypto)
-            set_property(TARGET OpenSSL::Crypto APPEND PROPERTY INTERFACE_LINK_LIBRARIES "dl")
-        endif()
-    endif()
-    find_package(Threads REQUIRED)
-    list(APPEND OPENSSL_LIBRARIES ${CMAKE_THREAD_LIBS_INIT})
-    if(TARGET OpenSSL::Crypto)
-        set_property(TARGET OpenSSL::Crypto APPEND PROPERTY INTERFACE_LINK_LIBRARIES "Threads::Threads")
-    endif()
-    if(TARGET OpenSSL::SSL)
-        set_property(TARGET OpenSSL::SSL APPEND PROPERTY INTERFACE_LINK_LIBRARIES "Threads::Threads")
-    endif()
-endif()
diff --git a/ports/openssl/vcpkg-cmake-wrapper.cmake b/ports/openssl/vcpkg-cmake-wrapper.cmake
index 6ef468ee6c6c25..0ff5788880e519 100644
--- a/ports/openssl/vcpkg-cmake-wrapper.cmake
+++ b/ports/openssl/vcpkg-cmake-wrapper.cmake
@@ -32,4 +32,34 @@ set(CMAKE_SYSTEM_IGNORE_PATH
 
 _find_package(${ARGS})
 
+if(OPENSSL_FOUND)
+    if("@OPENSSL_USE_WINDOWS_CMAKE_WRAPPER@")
+        list(APPEND OPENSSL_LIBRARIES crypt32.lib ws2_32.lib)
+        if(TARGET OpenSSL::Crypto)
+            set_property(TARGET OpenSSL::Crypto APPEND PROPERTY INTERFACE_LINK_LIBRARIES "crypt32.lib;ws2_32.lib")
+        endif()
+        if(TARGET OpenSSL::SSL)
+            set_property(TARGET OpenSSL::SSL APPEND PROPERTY INTERFACE_LINK_LIBRARIES "crypt32.lib;ws2_32.lib")
+        endif()
+    endif()
+
+    if("@OPENSSL_USE_UNIX_CMAKE_WRAPPER@")
+        find_library(OPENSSL_DL_LIBRARY NAMES dl)
+        if(OPENSSL_DL_LIBRARY)
+            list(APPEND OPENSSL_LIBRARIES "dl")
+            if(TARGET OpenSSL::Crypto)
+                set_property(TARGET OpenSSL::Crypto APPEND PROPERTY INTERFACE_LINK_LIBRARIES "dl")
+            endif()
+        endif()
+        find_package(Threads REQUIRED)
+        list(APPEND OPENSSL_LIBRARIES ${CMAKE_THREAD_LIBS_INIT})
+        if(TARGET OpenSSL::Crypto)
+            set_property(TARGET OpenSSL::Crypto APPEND PROPERTY INTERFACE_LINK_LIBRARIES "Threads::Threads")
+        endif()
+        if(TARGET OpenSSL::SSL)
+            set_property(TARGET OpenSSL::SSL APPEND PROPERTY INTERFACE_LINK_LIBRARIES "Threads::Threads")
+        endif()
+    endif()
+endif()
+
 set(OPENSSL_ROOT_DIR ${OPENSSL_ROOT_DIR_BAK})
diff --git a/ports/openssl/vcpkg.json b/ports/openssl/vcpkg.json
index 6dc21f4930b45f..9c4ec7f1e1117e 100644
--- a/ports/openssl/vcpkg.json
+++ b/ports/openssl/vcpkg.json
@@ -1,7 +1,7 @@
 {
   "name": "openssl",
   "version-string": "1.1.1k",
-  "port-version": 7,
+  "port-version": 8,
   "description": "OpenSSL is an open source project that provides a robust, commercial-grade, and full-featured toolkit for the Transport Layer Security (TLS) and Secure Sockets Layer (SSL) protocols. It is also a general-purpose cryptography library.",
   "homepage": "https://www.openssl.org"
 }
diff --git a/ports/openssl/windows/portfile.cmake b/ports/openssl/windows/portfile.cmake
index 3065abddc6f04f..633676b20988af 100644
--- a/ports/openssl/windows/portfile.cmake
+++ b/ports/openssl/windows/portfile.cmake
@@ -172,6 +172,4 @@ vcpkg_replace_string("${CURRENT_PACKAGES_DIR}/include/openssl/rand.h"
 vcpkg_copy_pdbs()
 
 file(INSTALL "${SOURCE_PATH}/LICENSE" DESTINATION "${CURRENT_PACKAGES_DIR}/share/${PORT}" RENAME copyright)
-if(VCPKG_LIBRARY_LINKAGE STREQUAL "static")
-    file(COPY "${CMAKE_CURRENT_LIST_DIR}/vcpkg-cmake-wrapper.cmake" DESTINATION "${CURRENT_PACKAGES_DIR}/share/openssl")
-endif()
+string(COMPARE EQUAL "${VCPKG_LIBRARY_LINKAGE}" "static" OPENSSL_USE_WINDOWS_CMAKE_WRAPPER)
diff --git a/ports/openssl/windows/vcpkg-cmake-wrapper.cmake b/ports/openssl/windows/vcpkg-cmake-wrapper.cmake
deleted file mode 100644
index 715448d25c170f..00000000000000
--- a/ports/openssl/windows/vcpkg-cmake-wrapper.cmake
+++ /dev/null
@@ -1,10 +0,0 @@
-_find_package(${ARGS})
-if(OPENSSL_FOUND)
-    list(APPEND OPENSSL_LIBRARIES Crypt32.lib ws2_32.lib)
-    if(TARGET OpenSSL::Crypto)
-        set_property(TARGET OpenSSL::Crypto APPEND PROPERTY INTERFACE_LINK_LIBRARIES "Crypt32.lib;ws2_32.lib")
-    endif()
-    if(TARGET OpenSSL::SSL)
-        set_property(TARGET OpenSSL::SSL APPEND PROPERTY INTERFACE_LINK_LIBRARIES "Crypt32.lib;ws2_32.lib")
-    endif()
-endif()
diff --git a/versions/baseline.json b/versions/baseline.json
index fd3faebe10ef89..eb3db466fb913d 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -4634,7 +4634,7 @@
     },
     "openssl": {
       "baseline": "1.1.1k",
-      "port-version": 7
+      "port-version": 8
     },
     "openssl-unix": {
       "baseline": "1.1.1h",
diff --git a/versions/o-/openssl.json b/versions/o-/openssl.json
index 474c91547d727b..eda47147ee0995 100644
--- a/versions/o-/openssl.json
+++ b/versions/o-/openssl.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "229509357a3a0dd7d286c771f344a821e3af752d",
+      "version-string": "1.1.1k",
+      "port-version": 8
+    },
     {
       "git-tree": "affa6f8de25994a485d4310cb56ddbc0df9ac705",
       "version-string": "1.1.1k",