diff --git a/ports/openssl/vcpkg.json b/ports/openssl/vcpkg.json
index 008c3fa130..a0619265e1 100644
--- a/ports/openssl/vcpkg.json
+++ b/ports/openssl/vcpkg.json
@@ -1,6 +1,7 @@
 {
   "name": "openssl",
   "version": "3.0.3",
+  "port-version": 1,
   "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",
   "license": "Apache-2.0",
@@ -8,6 +9,15 @@
     {
       "name": "vcpkg-cmake",
       "host": true
+    },
+    {
+      "name": "vcpkg-cmake-config",
+      "host": true
+    },
+    {
+      "name": "vcpkg-cmake-get-vars",
+      "host": true,
+      "platform": "windows & !mingw & !uwp"
     }
   ]
 }
diff --git a/ports/openssl/windows/flags.patch b/ports/openssl/windows/flags.patch
new file mode 100644
index 0000000000..90f0e89107
--- /dev/null
+++ b/ports/openssl/windows/flags.patch
@@ -0,0 +1,22 @@
+diff --git a/Configure b/Configure
+index faf57b1..690a9b8 100644
+--- a/Configure
++++ b/Configure
+@@ -556,7 +556,7 @@ my $list_separator_re =
+ # (we supported those before the change to "make variable" support.
+ my %user = (
+     AR          => env('AR'),
+-    ARFLAGS     => [],
++    ARFLAGS     => [ env('ARFLAGS') || () ],
+     AS          => undef,
+     ASFLAGS     => [],
+     CC          => env('CC'),
+@@ -569,7 +569,7 @@ my %user = (
+     CPPINCLUDES => [],  # Alternative for -I
+     CROSS_COMPILE => env('CROSS_COMPILE'),
+     HASHBANGPERL=> env('HASHBANGPERL') || env('PERL'),
+-    LD          => undef,
++    LD          => env('LD'),
+     LDFLAGS     => [ env('LDFLAGS') || () ],  # -L, -Wl,
+     LDLIBS      => [ env('LDLIBS') || () ],  # -l
+     MT          => undef,
diff --git a/ports/openssl/windows/portfile.cmake b/ports/openssl/windows/portfile.cmake
index 5cd4873002..f4f346e184 100644
--- a/ports/openssl/windows/portfile.cmake
+++ b/ports/openssl/windows/portfile.cmake
@@ -1,6 +1,7 @@
 vcpkg_extract_source_archive_ex(
     OUT_SOURCE_PATH SOURCE_PATH
     ARCHIVE ${ARCHIVE}
+    PATCHES "${CMAKE_CURRENT_LIST_DIR}/flags.patch"
 )
 
 vcpkg_find_acquire_program(NASM)
@@ -10,16 +11,29 @@ vcpkg_add_to_path(PREPEND "${NASM_EXE_PATH}")
 vcpkg_find_acquire_program(JOM)
 
 set(OPENSSL_SHARED no-shared)
-if(VCPKG_LIBRARY_LINKAGE STREQUAL dynamic)
+if(VCPKG_LIBRARY_LINKAGE STREQUAL "dynamic")
     set(OPENSSL_SHARED shared)
 endif()
 
+vcpkg_cmake_get_vars(cmake_vars_file)
+include("${cmake_vars_file}")
+
+set(ENV{CC} "${VCPKG_DETECTED_CMAKE_C_COMPILER}")
+set(ENV{CXX} "${VCPKG_DETECTED_CMAKE_CXX_COMPILER}")
+set(ENV{AR} "${VCPKG_DETECTED_CMAKE_AR}")
+set(ENV{LD} "${VCPKG_DETECTED_CMAKE_LINKER}")
+
+# OpenSSL's buildsystem hardcodes certain PDB manipulations, so we cannot use Z7
+string(REGEX REPLACE "(^| )-Z7($| )" " " VCPKG_COMBINED_C_FLAGS_RELEASE "${VCPKG_COMBINED_C_FLAGS_RELEASE}")
+string(REGEX REPLACE "(^| )-Z7($| )" " " VCPKG_COMBINED_C_FLAGS_DEBUG "${VCPKG_COMBINED_C_FLAGS_DEBUG}")
+string(REGEX REPLACE "(^| )-Z7($| )" " " VCPKG_COMBINED_CXX_FLAGS_RELEASE "${VCPKG_COMBINED_CXX_FLAGS_RELEASE}")
+string(REGEX REPLACE "(^| )-Z7($| )" " " VCPKG_COMBINED_CXX_FLAGS_DEBUG "${VCPKG_COMBINED_CXX_FLAGS_DEBUG}")
+
 set(CONFIGURE_OPTIONS
     enable-static-engine
     enable-capieng
     no-ssl2
     no-tests
-    -utf-8
     ${OPENSSL_SHARED}
 )
 
@@ -51,7 +65,6 @@ file(REMOVE_RECURSE "${CURRENT_BUILDTREES_DIR}/${TARGET_TRIPLET}-rel"
                     "${CURRENT_BUILDTREES_DIR}/${TARGET_TRIPLET}-dbg")
 
 if(NOT DEFINED VCPKG_BUILD_TYPE OR VCPKG_BUILD_TYPE STREQUAL "release")
-
     # Copy openssl sources.
     message(STATUS "Copying openssl release source files...")
     file(GLOB OPENSSL_SOURCE_FILES ${SOURCE_PATH}/*)
@@ -63,6 +76,11 @@ if(NOT DEFINED VCPKG_BUILD_TYPE OR VCPKG_BUILD_TYPE STREQUAL "release")
 
     set(OPENSSLDIR_RELEASE ${CURRENT_PACKAGES_DIR})
 
+    set(ENV{CFLAGS} "${VCPKG_COMBINED_C_FLAGS_RELEASE}")
+    set(ENV{CXXFLAGS} "${VCPKG_COMBINED_CXX_FLAGS_RELEASE}")
+    set(ENV{LDFLAGS} "${VCPKG_COMBINED_SHARED_LINKER_FLAGS_RELEASE}")
+    set(ENV{ARFLAGS} "${VCPKG_COMBINED_STATIC_LINKER_FLAGS_RELEASE}")
+
     message(STATUS "Configure ${TARGET_TRIPLET}-rel")
     vcpkg_execute_required_process(
         COMMAND ${CONFIGURE_COMMAND} ${OPENSSL_ARCH} "--prefix=${OPENSSLDIR_RELEASE}" "--openssldir=${OPENSSLDIR_RELEASE}" -FS
@@ -102,6 +120,11 @@ if(NOT DEFINED VCPKG_BUILD_TYPE OR VCPKG_BUILD_TYPE STREQUAL "debug")
 
     set(OPENSSLDIR_DEBUG ${CURRENT_PACKAGES_DIR}/debug)
 
+    set(ENV{CFLAGS} "${VCPKG_COMBINED_C_FLAGS_DEBUG}")
+    set(ENV{CXXFLAGS} "${VCPKG_COMBINED_CXX_FLAGS_DEBUG}")
+    set(ENV{LDFLAGS} "${VCPKG_COMBINED_SHARED_LINKER_FLAGS_DEBUG}")
+    set(ENV{ARFLAGS} "${VCPKG_COMBINED_STATIC_LINKER_FLAGS_DEBUG}")
+
     message(STATUS "Configure ${TARGET_TRIPLET}-dbg")
     vcpkg_execute_required_process(
         COMMAND ${CONFIGURE_COMMAND} debug-${OPENSSL_ARCH} "--prefix=${OPENSSLDIR_DEBUG}" "--openssldir=${OPENSSLDIR_DEBUG}" -FS
diff --git a/versions/baseline.json b/versions/baseline.json
index 3a15b5e832..5c78dcc9f7 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -5178,7 +5178,7 @@
     },
     "openssl": {
       "baseline": "3.0.3",
-      "port-version": 0
+      "port-version": 1
     },
     "openssl-unix": {
       "baseline": "1.1.1h",
diff --git a/versions/o-/openssl.json b/versions/o-/openssl.json
index 14d19fb958..93f7b62b5c 100644
--- a/versions/o-/openssl.json
+++ b/versions/o-/openssl.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "1ac5c972c2c6c9af050334b2f7a41de1253c6a5e",
+      "version": "3.0.3",
+      "port-version": 1
+    },
     {
       "git-tree": "973408910bc03c5a350f502080548a0d1ac68352",
       "version": "3.0.3",