diff --git a/scripts/test_ports/cmake-user/portfile.cmake b/scripts/test_ports/cmake-user/portfile.cmake
index 3999a49d64..d5fc746976 100644
--- a/scripts/test_ports/cmake-user/portfile.cmake
+++ b/scripts/test_ports/cmake-user/portfile.cmake
@@ -4,40 +4,50 @@ set(cmake_commands "")
 if("cmake-current" IN_LIST FEATURES)
     list(APPEND cmake_commands "${CMAKE_COMMAND}")
 endif()
-if("cmake-3-7" IN_LIST FEATURES)
-    set(cmake_version 3.7.2)
+if("cmake-3-16" IN_LIST FEATURES)
+    # For convenient updates, use 
+    # vcpkg install ... --cmake-args=-DVCPKG_CMAKE_USER_UPDATE=1
+    set(cmake_version 3.16.3)
+    set(legacy_cmake_archive NOTFOUND)
     string(REGEX REPLACE "([^.]*[.][^.]*).*" "\\1" cmake_major_minor "${cmake_version}")
-    if(VCPKG_HOST_IS_WINDOWS)
-        set(name "cmake-${cmake_version}-win32-x86")
+    if(VCPKG_HOST_IS_WINDOWS OR VCPKG_CMAKE_USER_UPDATE)
+        set(name "cmake-${cmake_version}-win64-x64")
         vcpkg_download_distfile(legacy_cmake_archive
             FILENAME "${name}.zip"
             URLS "https://github.com/Kitware/CMake/releases/download/v${cmake_version}/${name}.zip"
                  "https://cmake.org/files/v${cmake_major_minor}/${name}.zip"
-            SHA512 c359a22e2e688da1513db195280d6e8987bc8d570a0c543f1b1dfc8572fe4fd6c23d951ec5d5eae640fcca3bef3ae469083511474796ade8c6319d8bc4e4b38d
+            SHA512 724d22f3736f0f3503ceb6b49ebec64cd569c4c16ad4fae8ac38918b09ee67e3eaa8072e30546f14f4c13bb94c5639ec940ea1b4695c94225b2a597bb4da1ede
         )
         set(cmake_bin_dir "/bin")
-    elseif(VCPKG_HOST_IS_OSX)
+    endif()
+    if(VCPKG_HOST_IS_OSX OR VCPKG_CMAKE_USER_UPDATE)
         set(name "cmake-${cmake_version}-Darwin-x86_64")
         vcpkg_download_distfile(legacy_cmake_archive
             FILENAME "${name}.tar.gz"
             URLS "https://github.com/Kitware/CMake/releases/download/v${cmake_version}/${name}.tar.gz"
                  "https://cmake.org/files/v${cmake_major_minor}/${name}.tar.gz"
-            SHA512 8e41608f4dd998020acf2bd1b0dab4aec37b3ea9e228f2c4a457cd1c0339d94db38a0548b4b07a9e3605f9beb11a3f6737a72813586c4ad5f730d74038a14c2b
+            SHA512 3e59e2406f4e088b60922fbf23e92e1be3bb34c00f919625210fd93c059b5e6785afa40d3a501f36b281cde29de592f2ccffade6fa3980d0cf31dc845483184f
         )
         set(cmake_bin_dir "/CMake.app/Contents/bin")
-    elseif(VCPKG_HOST_IS_LINUX)
+    endif()
+    if(VCPKG_HOST_IS_LINUX OR VCPKG_CMAKE_USER_UPDATE)
         set(name "cmake-${cmake_version}-Linux-x86_64")
         vcpkg_download_distfile(legacy_cmake_archive
             FILENAME "${name}.tar.gz"
             URLS "https://github.com/Kitware/CMake/releases/download/v${cmake_version}/${name}.tar.gz"
                  "https://cmake.org/files/v${cmake_major_minor}/${name}.tar.gz"
-            SHA512 459909fcfb9c74993c3d4ab9db4e31ea940515b670db44d039de611d813099895e695467cc8da24824315486e38e2f3e246aa92d6236c51103822ec8a39e3168
+            SHA512 03be16ad06fcabe40a36d0a510fdb58f5612108aed70cef7f68879d82b9e04ad62a9d0c30f3406df618ec219c74fc27b4be533d970bc60ac22333951d6cabe1a
         )
         set(cmake_bin_dir "/bin")
-    else()
-        message(FATAL_ERROR "Unable to test feature 'cmake-3-7' for '${HOST_TRIPLET}' host.")
     endif()
-
+    if(NOT legacy_cmake_archive)
+        message(FATAL_ERROR "Unable to test feature 'cmake-3-16' for '${HOST_TRIPLET}' host.")
+    endif()
+    if(VCPKG_CMAKE_USER_UPDATE)
+        message(STATUS "All downloads are up-to-date.")
+        message(FATAL_ERROR "Stopping due to VCPKG_CMAKE_USER_UPDATE being enabled.")
+    endif()
+    
     vcpkg_extract_source_archive(legacy_cmake
         ARCHIVE "${legacy_cmake_archive}"
         SOURCE_BASE "${cmake_version}"
@@ -46,11 +56,7 @@ if("cmake-3-7" IN_LIST FEATURES)
     list(APPEND cmake_commands "${legacy_cmake}${cmake_bin_dir}/cmake")
 endif()
 
-if(DEFINED ENV{VCPKG_FORCE_SYSTEM_BINARIES})
-    set(NINJA "ninja")
-else()
-    vcpkg_find_acquire_program(NINJA)
-endif()
+vcpkg_find_acquire_program(NINJA)
 
 function(get_packages out_packages cmake_version)
     set(packages "")
diff --git a/scripts/test_ports/cmake-user/vcpkg.json b/scripts/test_ports/cmake-user/vcpkg.json
index 1197b1183a..241a18bcb5 100644
--- a/scripts/test_ports/cmake-user/vcpkg.json
+++ b/scripts/test_ports/cmake-user/vcpkg.json
@@ -1,36 +1,20 @@
 {
   "name": "cmake-user",
-  "version-date": "2022-11-12",
+  "version-string": "ci",
   "description": "Test port to verify the vcpkg toolchain in cmake user projects",
   "license": "MIT",
   "default-features": [
-    "ci"
+    {
+      "name": "cmake-3-16",
+      "platform": "x64 & (windows | linux | osx) & !uwp"
+    },
+    "cmake-current",
+    "find-package",
+    "pkg-check-modules"
   ],
   "features": {
-    "ci": {
-      "description": "The CI set of features to test",
-      "dependencies": [
-        {
-          "name": "cmake-user",
-          "default-features": false,
-          "features": [
-            "cmake-current",
-            "find-package",
-            "pkg-check-modules"
-          ]
-        },
-        {
-          "name": "cmake-user",
-          "default-features": false,
-          "features": [
-            "cmake-3-7"
-          ],
-          "platform": "x64 & (windows | linux | osx) & !uwp"
-        }
-      ]
-    },
-    "cmake-3-7": {
-      "description": "Run the tests with CMake 3.7"
+    "cmake-3-16": {
+      "description": "Run the tests with CMake 3.16"
     },
     "cmake-current": {
       "description": "Run the tests with vcpkg's current version of CMake"
@@ -58,14 +42,11 @@
         },
         {
           "$package": "Fontconfig",
-          "$since": "3.14",
           "name": "fontconfig",
           "platform": "!mingw & !uwp"
         },
         {
-          "$comment": "CMake 3.13 for debug postfix support",
           "$package": "GLUT",
-          "$since": "3.13",
           "name": "freeglut",
           "platform": "!uwp & !osx"
         },
@@ -75,9 +56,7 @@
           "default-features": false
         },
         {
-          "$comment": "CMake 3.9 for find_dependency forwarding extra arguments",
           "$package": "GDAL",
-          "$since": "3.9",
           "name": "gdal",
           "default-features": false,
           "platform": "!uwp"
@@ -107,7 +86,6 @@
         },
         {
           "$package": "Iconv",
-          "$since": "3.11",
           "name": "libiconv"
         },
         {
@@ -129,16 +107,12 @@
           "platform": "!uwp & !mingw"
         },
         {
-          "$comment": "CMake 3.11 because it needs Iconv",
           "$package": "LibXml2",
-          "$since": "3.11",
           "name": "libxml2",
           "default-features": false
         },
         {
-          "$comment": "CMake 3.11 because it needs Iconv",
           "$package": "LibXslt",
-          "$since": "3.11",
           "name": "libxslt",
           "default-features": false,
           "platform": "!uwp & !mingw"
@@ -159,7 +133,6 @@
         },
         {
           "$package": "SQLite3",
-          "$since": "3.14",
           "name": "sqlite3",
           "default-features": false
         },