diff --git a/ports/libressl/pkgconfig.diff b/ports/libressl/pkgconfig.diff
new file mode 100644
index 000000000..71381cdc5
--- /dev/null
+++ b/ports/libressl/pkgconfig.diff
@@ -0,0 +1,13 @@
+diff --git a/CMakeLists.txt b/CMakeLists.txt
+index 2172a48..e7458fd 100644
+--- a/CMakeLists.txt
++++ b/CMakeLists.txt
+@@ -529,7 +529,7 @@ if(ENABLE_LIBRESSL_INSTALL)
+ endif()
+ 
+ if(ENABLE_LIBRESSL_INSTALL)
+-	if(NOT MSVC)
++	if(1)
+ 		# Create pkgconfig files.
+ 		set(prefix      ${CMAKE_INSTALL_PREFIX})
+ 		set(exec_prefix \${prefix})
diff --git a/ports/libressl/portfile.cmake b/ports/libressl/portfile.cmake
index 1d9c74e39..3aa0716aa 100644
--- a/ports/libressl/portfile.cmake
+++ b/ports/libressl/portfile.cmake
@@ -15,6 +15,7 @@ vcpkg_extract_source_archive(
     ARCHIVE "${LIBRESSL_SOURCE_ARCHIVE}"
     PATCHES
         0002-suppress-msvc-warnings.patch
+        pkgconfig.diff
 )
 
 vcpkg_check_features(OUT_FEATURE_OPTIONS FEATURE_OPTIONS
@@ -26,35 +27,30 @@ vcpkg_cmake_configure(
     SOURCE_PATH "${SOURCE_PATH}"
     OPTIONS
         ${FEATURE_OPTIONS}
+        -DLIBRESSL_INSTALL_CMAKEDIR=share/${PORT}
         -DLIBRESSL_TESTS=OFF
     OPTIONS_DEBUG
         -DLIBRESSL_APPS=OFF
 )
 
 vcpkg_cmake_install()
+vcpkg_copy_pdbs()
+vcpkg_fixup_pkgconfig()
+vcpkg_cmake_config_fixup()
+
+# libressl as openssl replacement
+configure_file("${CURRENT_PORT_DIR}/vcpkg-cmake-wrapper.cmake.in" "${CURRENT_PACKAGES_DIR}/share/openssl/vcpkg-cmake-wrapper.cmake" @ONLY)
 
 if("tools" IN_LIST FEATURES)
     vcpkg_copy_tools(TOOL_NAMES ocspcheck openssl DESTINATION "${CURRENT_PACKAGES_DIR}/tools/openssl" AUTO_CLEAN)
 endif()
 
-if(VCPKG_LIBRARY_LINKAGE STREQUAL "static")
-    file(REMOVE_RECURSE
-        "${CURRENT_PACKAGES_DIR}/bin"
-        "${CURRENT_PACKAGES_DIR}/debug/bin"
-    )
-endif()
 file(REMOVE_RECURSE
     "${CURRENT_PACKAGES_DIR}/etc/ssl/certs"
     "${CURRENT_PACKAGES_DIR}/debug/etc/ssl/certs"
-    "${CURRENT_PACKAGES_DIR}/share/man"
     "${CURRENT_PACKAGES_DIR}/debug/include"
     "${CURRENT_PACKAGES_DIR}/debug/share"
+    "${CURRENT_PACKAGES_DIR}/share/man"
 )
 
-vcpkg_copy_pdbs()
-
 vcpkg_install_copyright(FILE_LIST "${SOURCE_PATH}/COPYING")
-
-vcpkg_fixup_pkgconfig()
-vcpkg_cmake_config_fixup(CONFIG_PATH "lib/cmake/LibreSSL")
-file(REMOVE_RECURSE "${CURRENT_PACKAGES_DIR}/debug/share")
diff --git a/ports/libressl/vcpkg-cmake-wrapper.cmake.in b/ports/libressl/vcpkg-cmake-wrapper.cmake.in
new file mode 100644
index 000000000..70be9cc3e
--- /dev/null
+++ b/ports/libressl/vcpkg-cmake-wrapper.cmake.in
@@ -0,0 +1,75 @@
+cmake_policy(PUSH)
+cmake_policy(SET CMP0012 NEW)
+cmake_policy(SET CMP0054 NEW)
+cmake_policy(SET CMP0057 NEW)
+
+# opensslv.h: OPENSSL_VERSION_NUMBER 0x20000000L, "These will never change"
+set(OPENSSL_VERSION_MAJOR 2)
+set(OPENSSL_VERSION_MINOR 0)
+set(OPENSSL_VERSION_FIX 0)
+
+if(OPENSSL_USE_STATIC_LIBS)
+    if("@VCPKG_LIBRARY_LINKAGE@" STREQUAL "dynamic")
+        message(WARNING "OPENSSL_USE_STATIC_LIBS is set, but vcpkg port openssl was built with dynamic linkage")
+    endif()
+    set(OPENSSL_USE_STATIC_LIBS_BAK "${OPENSSL_USE_STATIC_LIBS}")
+    set(OPENSSL_USE_STATIC_LIBS FALSE)
+endif()
+
+if(DEFINED OPENSSL_ROOT_DIR)
+    set(OPENSSL_ROOT_DIR_BAK "${OPENSSL_ROOT_DIR}")
+endif()
+get_filename_component(OPENSSL_ROOT_DIR "${CMAKE_CURRENT_LIST_DIR}" DIRECTORY)
+get_filename_component(OPENSSL_ROOT_DIR "${OPENSSL_ROOT_DIR}" DIRECTORY)
+find_path(OPENSSL_INCLUDE_DIR NAMES openssl/ssl.h PATH "${OPENSSL_ROOT_DIR}/include" NO_DEFAULT_PATH)
+if(MSVC)
+    find_library(LIB_EAY_DEBUG NAMES crypto PATHS "${OPENSSL_ROOT_DIR}/debug/lib" NO_DEFAULT_PATH)
+    find_library(LIB_EAY_RELEASE NAMES crypto PATHS "${OPENSSL_ROOT_DIR}/lib" NO_DEFAULT_PATH)
+    find_library(SSL_EAY_DEBUG NAMES ssl PATHS "${OPENSSL_ROOT_DIR}/debug/lib" NO_DEFAULT_PATH)
+    find_library(SSL_EAY_RELEASE NAMES ssl PATHS "${OPENSSL_ROOT_DIR}/lib" NO_DEFAULT_PATH)
+elseif(WIN32)
+    find_library(LIB_EAY NAMES libcrypto crypto NAMES_PER_DIR)
+    find_library(SSL_EAY NAMES libssl ssl NAMES_PER_DIR)
+else()
+    find_library(OPENSSL_CRYPTO_LIBRARY NAMES crypto)
+    find_library(OPENSSL_SSL_LIBRARY NAMES ssl)
+endif()
+
+_find_package(${ARGS})
+
+unset(OPENSSL_ROOT_DIR)
+if(DEFINED OPENSSL_ROOT_DIR_BAK)
+    set(OPENSSL_ROOT_DIR "${OPENSSL_ROOT_DIR_BAK}")
+    unset(OPENSSL_ROOT_DIR_BAK)
+endif()
+
+if(DEFINED OPENSSL_USE_STATIC_LIBS_BAK)
+    set(OPENSSL_USE_STATIC_LIBS "${OPENSSL_USE_STATIC_LIBS_BAK}")
+    unset(OPENSSL_USE_STATIC_LIBS_BAK)
+endif()
+
+if(OPENSSL_FOUND AND "@VCPKG_LIBRARY_LINKAGE@" STREQUAL "static")
+    if(WIN32)
+        list(APPEND OPENSSL_LIBRARIES ws2_32 ntdll bcrypt)
+        if(TARGET OpenSSL::Crypto)
+            set_property(TARGET OpenSSL::Crypto APPEND PROPERTY INTERFACE_LINK_LIBRARIES "ws2_32;ntdll;bcrypt")
+        endif()
+        if(TARGET OpenSSL::SSL)
+            set_property(TARGET OpenSSL::SSL APPEND PROPERTY INTERFACE_LINK_LIBRARIES "ws2_32;ntdll;bcrypt")
+        endif()
+    else()
+        if("REQUIRED" IN_LIST ARGS)
+           find_package(Threads REQUIRED)
+        else()
+           find_package(Threads)
+        endif()
+        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()
+cmake_policy(POP)
diff --git a/ports/libressl/vcpkg.json b/ports/libressl/vcpkg.json
index 497e5effb..00effcc9d 100644
--- a/ports/libressl/vcpkg.json
+++ b/ports/libressl/vcpkg.json
@@ -1,8 +1,13 @@
 {
   "name": "libressl",
   "version": "3.9.2",
-  "port-version": 1,
-  "description": "LibreSSL is a version of the TLS/crypto stack forked from OpenSSL in 2014, with goals of modernizing the codebase, improving security, and applying best practice development processes.",
+  "port-version": 2,
+  "description": [
+    "LibreSSL is a TLS/crypto stack.",
+    "It was forked from OpenSSL in 2014 by the OpenBSD project, with goals of modernizing the codebase, improving security, and applying best practice development processes.",
+    "LibreSSL provides much of the OpenSSL 1.1 API. Incompatibilities between the projects exist and are unavoidable since both evolve with different goals and priorities."
+  ],
+  "homepage": "https://www.libressl.org",
   "license": "ISC",
   "dependencies": [
     {
diff --git a/scripts/test_ports/vcpkg-ci-libressl/portfile.cmake b/scripts/test_ports/vcpkg-ci-libressl/portfile.cmake
index bc785962c..dd2570612 100644
--- a/scripts/test_ports/vcpkg-ci-libressl/portfile.cmake
+++ b/scripts/test_ports/vcpkg-ci-libressl/portfile.cmake
@@ -1,4 +1,10 @@
 set(VCPKG_POLICY_EMPTY_PACKAGE enabled)
 
-vcpkg_cmake_configure(SOURCE_PATH "${CURRENT_PORT_DIR}/project")
+vcpkg_find_acquire_program(PKGCONFIG)
+
+vcpkg_cmake_configure(
+    SOURCE_PATH "${CURRENT_PORT_DIR}/project"
+    OPTIONS
+        "-DPKG_CONFIG_EXECUTABLE=${PKGCONFIG}"
+)
 vcpkg_cmake_build()
diff --git a/scripts/test_ports/vcpkg-ci-libressl/project/CMakeLists.txt b/scripts/test_ports/vcpkg-ci-libressl/project/CMakeLists.txt
index ba70f6b1c..33f6bad32 100644
--- a/scripts/test_ports/vcpkg-ci-libressl/project/CMakeLists.txt
+++ b/scripts/test_ports/vcpkg-ci-libressl/project/CMakeLists.txt
@@ -1,5 +1,20 @@
 cmake_minimum_required(VERSION 3.7)
-project(libressl-test CXX)
+project(libressl-test C)
+
+find_package(PkgConfig REQUIRED)
+
+# libressl provides cmake config
+find_package(LibreSSL CONFIG REQUIRED)
+message(STATUS "LibreSSL CONFIG: ${LibreSSL_DIR}")
+string(FIND "${LibreSSL_DIR}" "${VCPKG_INSTALLED_DIR}/${VCPKG_TARGET_TRIPLET}" index)
+if(NOT index STREQUAL "0")
+    message(SEND_ERROR "LibreSSL CONFIG is not from vcpkg.")
+endif()
+
+pkg_check_modules(libtls IMPORTED_TARGET REQUIRED libtls)
+if(NOT libtls_VERSION STREQUAL LibreSSL_VERSION)
+    message(SEND_ERROR "Unexpected libtls_VERSION '${libtls_VERSION}' (expected: '${LibreSSL_VERSION}')")
+endif()
 
 # libressl promises openssl compatibility
 # NB: The port doesn't provide a wrapper, so there is no support
@@ -23,11 +38,26 @@ foreach(target IN ITEMS OpenSSL::SSL OpenSSL::Crypto)
         message(SEND_ERROR "No location for ${target} binary")
     endif()
 endforeach()
+if(NOT OPENSSL_VERSION STREQUAL "2.0.0")
+    message(SEND_ERROR "Unexpected OPENSSL_VERSION '${OPENSSL_VERSION}' (expected: '2.0.0')")
+endif()
 
-# libressl provides cmake config
-find_package(LibreSSL CONFIG REQUIRED)
-message(STATUS "LibreSSL CONFIG: ${LibreSSL_DIR}")
-string(FIND "${LibreSSL_DIR}" "${VCPKG_INSTALLED_DIR}/${VCPKG_TARGET_TRIPLET}" index)
-if(NOT index STREQUAL "0")
-    message(SEND_ERROR "LibreSSL CONFIG is not from vcpkg.")
+pkg_check_modules(openssl IMPORTED_TARGET REQUIRED openssl)
+# NB: openssl.pc carries libressl version (3.x), but doesn't provide 3.x OpenSSL API.
+if(NOT openssl_VERSION STREQUAL LibreSSL_VERSION)
+    message(SEND_ERROR "Unexpected openssl_VERSION '${openssl_VERSION}' (expected: '${LibreSSL_VERSION}')")
 endif()
+
+# compile and link tests
+
+add_executable(openssl_cmake openssl.c)
+target_link_libraries(openssl_cmake OpenSSL::SSL)
+
+add_executable(openssl_pkgconfig openssl.c)
+target_link_libraries(openssl_pkgconfig PkgConfig::openssl)
+
+add_executable(libressl_cmake libressl.c)
+target_link_libraries(libressl_cmake LibreSSL::TLS)
+
+add_executable(libressl_pkgconfig libressl.c)
+target_link_libraries(libressl_pkgconfig PkgConfig::libtls)
diff --git a/scripts/test_ports/vcpkg-ci-libressl/project/libressl.c b/scripts/test_ports/vcpkg-ci-libressl/project/libressl.c
new file mode 100644
index 000000000..2814d3c46
--- /dev/null
+++ b/scripts/test_ports/vcpkg-ci-libressl/project/libressl.c
@@ -0,0 +1,6 @@
+#include <tls.h>
+
+int main()
+{
+  return tls_init();
+}
diff --git a/scripts/test_ports/vcpkg-ci-libressl/project/openssl.c b/scripts/test_ports/vcpkg-ci-libressl/project/openssl.c
new file mode 100644
index 000000000..880991a88
--- /dev/null
+++ b/scripts/test_ports/vcpkg-ci-libressl/project/openssl.c
@@ -0,0 +1,10 @@
+#include <openssl/ssl.h>
+
+#if OPENSSL_VERSION_NUMBER != 0x20000000L
+#  error Unexpected version
+#endif
+
+int main()
+{
+  return SSL_library_init();
+}
diff --git a/versions/baseline.json b/versions/baseline.json
index af08aecac..490b39b4c 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -4998,7 +4998,7 @@
     },
     "libressl": {
       "baseline": "3.9.2",
-      "port-version": 1
+      "port-version": 2
     },
     "librsvg": {
       "baseline": "2.40.20",
diff --git a/versions/l-/libressl.json b/versions/l-/libressl.json
index ba5ecdb46..2e4e1ec45 100644
--- a/versions/l-/libressl.json
+++ b/versions/l-/libressl.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "a4db7a421fd0fe40d7c56014e8b6cf4e5a9c2525",
+      "version": "3.9.2",
+      "port-version": 2
+    },
     {
       "git-tree": "f9e56b0af8f93ed5c5adc5e2ba1696e5c16420be",
       "version": "3.9.2",