diff --git a/ports/openssl/portfile.cmake b/ports/openssl/portfile.cmake
index ff65db49b1..4a51777ab1 100644
--- a/ports/openssl/portfile.cmake
+++ b/ports/openssl/portfile.cmake
@@ -3,7 +3,16 @@ if(EXISTS "${CURRENT_INSTALLED_DIR}/share/libressl/copyright"
     message(FATAL_ERROR "Can't build openssl if libressl/boringssl is installed. Please remove libressl/boringssl, and try install openssl again if you need it.")
 endif()
 
+if (VCPKG_TARGET_IS_LINUX)
+    message(WARNING
+[[openssl currently requires the following library from the system package manager:
+    linux-headers
+It can be installed on alpine systems via apk add linux-headers.]]
+    )
+endif()
+
 set(OPENSSL_VERSION 3.0.2)
+
 vcpkg_download_distfile(
     ARCHIVE
     URLS "https://www.openssl.org/source/openssl-${OPENSSL_VERSION}.tar.gz"
diff --git a/ports/openssl/vcpkg.json b/ports/openssl/vcpkg.json
index 8f6c3067f8..dd48bdec52 100644
--- a/ports/openssl/vcpkg.json
+++ b/ports/openssl/vcpkg.json
@@ -1,9 +1,10 @@
 {
   "name": "openssl",
   "version": "3.0.2",
+  "port-version": 1,
   "description": "OpenSSL is an open source project that provides a robust, commercial-grade, and full-featured toolkit for the Transport Layer Security (TLS) and Secure Sockets Layer (SSL) protocols. It is also a general-purpose cryptography library.",
   "homepage": "https://www.openssl.org",
-  "license": "OpenSSL",
+  "license": "Apache-2.0",
   "dependencies": [
     {
       "name": "vcpkg-cmake",
diff --git a/ports/openssl/windows/portfile.cmake b/ports/openssl/windows/portfile.cmake
index e5356959af..2e85ec5f00 100644
--- a/ports/openssl/windows/portfile.cmake
+++ b/ports/openssl/windows/portfile.cmake
@@ -122,9 +122,9 @@ if(NOT DEFINED VCPKG_BUILD_TYPE OR VCPKG_BUILD_TYPE STREQUAL "debug")
         COMMAND "${JOM}" -j 1 -f "${OPENSSL_MAKEFILE}" install_sw install_ssldirs
         WORKING_DIRECTORY ${SOURCE_PATH_DEBUG}
         LOGNAME build-${TARGET_TRIPLET}-dbg-1)
-        
+
         message(STATUS "Build ${TARGET_TRIPLET}-dbg done")
-        
+
         file(RENAME "${CURRENT_PACKAGES_DIR}/debug/lib/ossl-modules/legacy.pdb" "${CURRENT_PACKAGES_DIR}/debug/bin/legacy.pdb")
         file(RENAME "${CURRENT_PACKAGES_DIR}/lib/ossl-modules/legacy.pdb" "${CURRENT_PACKAGES_DIR}/bin/legacy.pdb")
 endif()
@@ -139,8 +139,11 @@ file(REMOVE_RECURSE "${CURRENT_PACKAGES_DIR}/debug/lib/engines-3")
 file(REMOVE_RECURSE "${CURRENT_PACKAGES_DIR}/debug/private")
 file(REMOVE_RECURSE "${CURRENT_PACKAGES_DIR}/debug/include")
 
-file(RENAME "${CURRENT_PACKAGES_DIR}/debug/lib/ossl-modules/legacy.dll" "${CURRENT_PACKAGES_DIR}/debug/bin/legacy.dll")
+if(NOT VCPKG_BUILD_TYPE)
+    file(RENAME "${CURRENT_PACKAGES_DIR}/debug/lib/ossl-modules/legacy.dll" "${CURRENT_PACKAGES_DIR}/debug/bin/legacy.dll")
+endif()
 file(RENAME "${CURRENT_PACKAGES_DIR}/lib/ossl-modules/legacy.dll" "${CURRENT_PACKAGES_DIR}/bin/legacy.dll")
+
 file(REMOVE_RECURSE "${CURRENT_PACKAGES_DIR}/debug/lib/ossl-modules")
 file(REMOVE_RECURSE "${CURRENT_PACKAGES_DIR}/lib/ossl-modules")
 
diff --git a/versions/baseline.json b/versions/baseline.json
index 5d31b8fedf..63f37ea59c 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -5142,7 +5142,7 @@
     },
     "openssl": {
       "baseline": "3.0.2",
-      "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 1ea6e851f5..113320c810 100644
--- a/versions/o-/openssl.json
+++ b/versions/o-/openssl.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "3505d3717ae864160fdb273eb2ec9d614eb6711e",
+      "version": "3.0.2",
+      "port-version": 1
+    },
     {
       "git-tree": "2ba2e59ee4f32c11e30aeccc0ecabc09b69c5d22",
       "version": "3.0.2",