diff --git a/ports/libressl/portfile.cmake b/ports/libressl/portfile.cmake
index d957d8783e0cda..b8604ebfda33ad 100644
--- a/ports/libressl/portfile.cmake
+++ b/ports/libressl/portfile.cmake
@@ -4,20 +4,20 @@ if(EXISTS "${CURRENT_INSTALLED_DIR}/include/openssl/ssl.h")
   return()
 endif()
 
-set(LIBRESSL_VERSION 3.3.4)
-set(LIBRESSL_HASH 11defdde8169d3653c24e149e698ffc5a8ead5ac0808111d1986cb11ef72e9912c463d4891d4635877021e73a8a045dbdbe5e83ec785a59150f170d2ca2031de)
+set(LIBRESSL_VERSION 3.4.2)
+set(LIBRESSL_HASH ae91a840b29330681dc2a4f55a9bd760e6fe1bdfb3399017aae3a16bd21b413e97cbb8ba504400f0a1f42757f6128b3fa763d06bae4fc9f2b9dbeea867a57ad2)
 
 vcpkg_download_distfile(
     LIBRESSL_SOURCE_ARCHIVE
-    URLS https://ftp.openbsd.org/pub/OpenBSD/LibreSSL/${PORT}-${LIBRESSL_VERSION}.tar.gz https://ftp.fau.de/openbsd/LibreSSL/${PORT}-${LIBRESSL_VERSION}.tar.gz
-    FILENAME ${PORT}-${LIBRESSL_VERSION}.tar.gz
-    SHA512 ${LIBRESSL_HASH}
+    URLS "https://ftp.openbsd.org/pub/OpenBSD/LibreSSL/${PORT}-${LIBRESSL_VERSION}.tar.gz" "https://ftp.fau.de/openbsd/LibreSSL/${PORT}-${LIBRESSL_VERSION}.tar.gz"
+    FILENAME "${PORT}-${LIBRESSL_VERSION}.tar.gz"
+    SHA512 "${LIBRESSL_HASH}"
 )
 
 vcpkg_extract_source_archive_ex(
     OUT_SOURCE_PATH SOURCE_PATH
     ARCHIVE "${LIBRESSL_SOURCE_ARCHIVE}"
-    REF ${LIBRESSL_VERSION}
+    REF "${LIBRESSL_VERSION}"
     PATCHES
         0001-enable-ocspcheck-on-msvc.patch
         0002-suppress-msvc-warnings.patch
@@ -65,6 +65,6 @@ if(VCPKG_TARGET_IS_WINDOWS OR VCPKG_TARGET_IS_UWP)
     file(GLOB_RECURSE LIBS "${CURRENT_PACKAGES_DIR}/*.lib")
     foreach(LIB ${LIBS})
         string(REGEX REPLACE "(.+)-[0-9]+\\.lib" "\\1.lib" LINK "${LIB}")
-        execute_process(COMMAND "${CMAKE_COMMAND}" -E create_symlink "${LIB}" "${LINK}")
+        file(CREATE_LINK "${LIB}" "${LINK}")
     endforeach()
 endif()
diff --git a/ports/libressl/vcpkg.json b/ports/libressl/vcpkg.json
index f6afd1026741c1..3b784e025024b5 100644
--- a/ports/libressl/vcpkg.json
+++ b/ports/libressl/vcpkg.json
@@ -1,7 +1,6 @@
 {
   "name": "libressl",
-  "version": "3.3.4",
-  "port-version": 1,
+  "version": "3.4.2",
   "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.",
   "supports": "!(uwp | arm)",
   "dependencies": [
diff --git a/versions/baseline.json b/versions/baseline.json
index 1286dcf59dd1b6..666052049cb817 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -3877,8 +3877,8 @@
       "port-version": 0
     },
     "libressl": {
-      "baseline": "3.3.4",
-      "port-version": 1
+      "baseline": "3.4.2",
+      "port-version": 0
     },
     "librsvg": {
       "baseline": "2.40.20",
diff --git a/versions/l-/libressl.json b/versions/l-/libressl.json
index d750caba6b26c7..7312a9eda54fc2 100644
--- a/versions/l-/libressl.json
+++ b/versions/l-/libressl.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "09613175bb9f051a273b68c0520ad4017d8fabd9",
+      "version": "3.4.2",
+      "port-version": 0
+    },
     {
       "git-tree": "1541c15439fdf9199c6796b51cd59fa644b7d9e4",
       "version": "3.3.4",