diff --git a/ports/openssl/unix/portfile.cmake b/ports/openssl/unix/portfile.cmake
index 414da82d8f16f7..78c0ea2f8a4601 100644
--- a/ports/openssl/unix/portfile.cmake
+++ b/ports/openssl/unix/portfile.cmake
@@ -115,7 +115,9 @@ vcpkg_fixup_pkgconfig()
 file(MAKE_DIRECTORY "${CURRENT_PACKAGES_DIR}/tools/${PORT}")
 file(RENAME "${CURRENT_PACKAGES_DIR}/bin/c_rehash" "${CURRENT_PACKAGES_DIR}/tools/${PORT}/c_rehash")
 file(REMOVE "${CURRENT_PACKAGES_DIR}/debug/bin/c_rehash")
-vcpkg_copy_tools(TOOL_NAMES openssl AUTO_CLEAN)
+if (NOT VCPKG_CROSSCOMPILING)
+  vcpkg_copy_tools(TOOL_NAMES openssl AUTO_CLEAN)
+endif()
 
 file(TOUCH "${CURRENT_PACKAGES_DIR}/etc/ssl/certs/.keep")
 file(TOUCH "${CURRENT_PACKAGES_DIR}/etc/ssl/private/.keep")
diff --git a/ports/openssl/vcpkg.json b/ports/openssl/vcpkg.json
index 790c240aea6eb1..acb8fcaf6a6aea 100644
--- a/ports/openssl/vcpkg.json
+++ b/ports/openssl/vcpkg.json
@@ -1,7 +1,7 @@
 {
   "name": "openssl",
   "version": "3.0.8",
-  "port-version": 1,
+  "port-version": 2,
   "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",
diff --git a/versions/baseline.json b/versions/baseline.json
index b2196cb145117a..86ccf1931f34e9 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -5762,7 +5762,7 @@
     },
     "openssl": {
       "baseline": "3.0.8",
-      "port-version": 1
+      "port-version": 2
     },
     "openssl-unix": {
       "baseline": "deprecated",
diff --git a/versions/o-/openssl.json b/versions/o-/openssl.json
index 4d0005e41a989a..26268a60060c36 100644
--- a/versions/o-/openssl.json
+++ b/versions/o-/openssl.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "2a8d35c58ab2dacda462495d5d4a0ea92e574e39",
+      "version": "3.0.8",
+      "port-version": 2
+    },
     {
       "git-tree": "17ce011827417025d6a29924ace0a474f1689c65",
       "version": "3.0.8",