diff --git a/ports/python2/CONTROL b/ports/python2/CONTROL
deleted file mode 100644
index 6d6c32a4daaba1..00000000000000
--- a/ports/python2/CONTROL
+++ /dev/null
@@ -1,3 +0,0 @@
-Source: python2
-Version: 2.7.18
-Description: The Python programming language as an embeddable library
diff --git a/ports/python2/portfile.cmake b/ports/python2/portfile.cmake
index f111a9eb7b0ecc..fdbf8f415b97a6 100644
--- a/ports/python2/portfile.cmake
+++ b/ports/python2/portfile.cmake
@@ -13,6 +13,14 @@ set(PYTHON_VERSION_PATCH  18)
 set(PYTHON_VERSION        ${PYTHON_VERSION_MAJOR}.${PYTHON_VERSION_MINOR}.${PYTHON_VERSION_PATCH})
 
 set(_PYTHON_PATCHES "")
+if (VCPKG_TARGET_IS_WINDOWS)
+    list(APPEND _PYTHON_PATCHES
+        ${CMAKE_CURRENT_LIST_DIR}/001-build-msvc.patch
+        ${CMAKE_CURRENT_LIST_DIR}/002-build-msvc.patch
+        ${CMAKE_CURRENT_LIST_DIR}/003-build-msvc.patch
+    )
+endif()
+
 if (VCPKG_LIBRARY_LINKAGE STREQUAL static)
     list(APPEND _PYTHON_PATCHES
         ${CMAKE_CURRENT_LIST_DIR}/004-static-library-msvc.patch
@@ -23,6 +31,12 @@ if (VCPKG_CRT_LINKAGE STREQUAL static)
     list(APPEND _PYTHON_PATCHES ${CMAKE_CURRENT_LIST_DIR}/005-static-crt-msvc.patch)
 endif()
 
+if (VCPKG_TARGET_IS_WINDOWS)
+    list(APPEND _PYTHON_PATCHES
+        ${CMAKE_CURRENT_LIST_DIR}/007-fix-build-path.patch
+    )
+endif()
+
 
 vcpkg_download_distfile(ARCHIVE
     URLS https://www.python.org/ftp/python/${PYTHON_VERSION}/Python-${PYTHON_VERSION}.tar.xz
@@ -33,43 +47,48 @@ vcpkg_download_distfile(ARCHIVE
 vcpkg_extract_source_archive_ex(
     OUT_SOURCE_PATH SOURCE_PATH
     ARCHIVE ${ARCHIVE}
-    PATCHES
-    PATCHES
-        ${CMAKE_CURRENT_LIST_DIR}/001-build-msvc.patch
-        ${CMAKE_CURRENT_LIST_DIR}/002-build-msvc.patch
-        ${CMAKE_CURRENT_LIST_DIR}/003-build-msvc.patch
-        ${_PYTHON_PATCHES}
-        ${CMAKE_CURRENT_LIST_DIR}/007-fix-build-path.patch
+    PATCHES ${_PYTHON_PATCHES}
 )
 
-if (VCPKG_TARGET_ARCHITECTURE MATCHES "x86")
-    set(BUILD_ARCH "Win32")
-    set(OUT_DIR "win32")
-elseif (VCPKG_TARGET_ARCHITECTURE MATCHES "x64")
-    set(BUILD_ARCH "x64")
-    set(OUT_DIR "amd64")
-else()
-    message(FATAL_ERROR "Unsupported architecture: ${VCPKG_TARGET_ARCHITECTURE}")
-endif()
-
-vcpkg_build_msbuild(
-    PROJECT_PATH ${SOURCE_PATH}/PCBuild/pythoncore.vcxproj
-    PLATFORM ${BUILD_ARCH})
-
-file(GLOB HEADERS ${SOURCE_PATH}/Include/*.h)
-file(COPY ${HEADERS} ${SOURCE_PATH}/PC/pyconfig.h DESTINATION ${CURRENT_PACKAGES_DIR}/include/python${PYTHON_VERSION_MAJOR}.${PYTHON_VERSION_MINOR})
-
-file(COPY ${SOURCE_PATH}/Lib DESTINATION ${CURRENT_PACKAGES_DIR}/share/python${PYTHON_VERSION_MAJOR})
+if (VCPKG_TARGET_IS_WINDOWS)
+    if (VCPKG_TARGET_ARCHITECTURE MATCHES "x86")
+        set(BUILD_ARCH "Win32")
+        set(OUT_DIR "win32")
+    elseif (VCPKG_TARGET_ARCHITECTURE MATCHES "x64")
+        set(BUILD_ARCH "x64")
+        set(OUT_DIR "amd64")
+    else()
+        message(FATAL_ERROR "Unsupported architecture: ${VCPKG_TARGET_ARCHITECTURE}")
+    endif()
+    
+    vcpkg_build_msbuild(
+        PROJECT_PATH ${SOURCE_PATH}/PCBuild/pythoncore.vcxproj
+        PLATFORM ${BUILD_ARCH}
+    )
 
-file(COPY ${SOURCE_PATH}/PCBuild/${OUT_DIR}/python${PYTHON_VERSION_MAJOR}${PYTHON_VERSION_MINOR}.lib DESTINATION ${CURRENT_PACKAGES_DIR}/lib)
-file(COPY ${SOURCE_PATH}/PCBuild/${OUT_DIR}/python${PYTHON_VERSION_MAJOR}${PYTHON_VERSION_MINOR}_d.lib DESTINATION ${CURRENT_PACKAGES_DIR}/debug/lib)
-if (VCPKG_LIBRARY_LINKAGE STREQUAL dynamic)
-    file(COPY ${SOURCE_PATH}/PCBuild/${OUT_DIR}/python${PYTHON_VERSION_MAJOR}${PYTHON_VERSION_MINOR}.dll DESTINATION ${CURRENT_PACKAGES_DIR}/bin)
-    file(COPY ${SOURCE_PATH}/PCBuild/${OUT_DIR}/python${PYTHON_VERSION_MAJOR}${PYTHON_VERSION_MINOR}_d.dll DESTINATION ${CURRENT_PACKAGES_DIR}/debug/bin)
+    vcpkg_copy_pdbs()
+    
+    file(GLOB HEADERS ${SOURCE_PATH}/Include/*.h)
+    file(COPY ${HEADERS} ${SOURCE_PATH}/PC/pyconfig.h DESTINATION ${CURRENT_PACKAGES_DIR}/include/python${PYTHON_VERSION_MAJOR}.${PYTHON_VERSION_MINOR})
+    
+    file(COPY ${SOURCE_PATH}/Lib DESTINATION ${CURRENT_PACKAGES_DIR}/share/python${PYTHON_VERSION_MAJOR})
+    
+    file(COPY ${SOURCE_PATH}/PCBuild/${OUT_DIR}/python${PYTHON_VERSION_MAJOR}${PYTHON_VERSION_MINOR}.lib DESTINATION ${CURRENT_PACKAGES_DIR}/lib)
+    file(COPY ${SOURCE_PATH}/PCBuild/${OUT_DIR}/python${PYTHON_VERSION_MAJOR}${PYTHON_VERSION_MINOR}_d.lib DESTINATION ${CURRENT_PACKAGES_DIR}/debug/lib)
+    if (VCPKG_LIBRARY_LINKAGE STREQUAL dynamic)
+        file(COPY ${SOURCE_PATH}/PCBuild/${OUT_DIR}/python${PYTHON_VERSION_MAJOR}${PYTHON_VERSION_MINOR}.dll DESTINATION ${CURRENT_PACKAGES_DIR}/bin)
+        file(COPY ${SOURCE_PATH}/PCBuild/${OUT_DIR}/python${PYTHON_VERSION_MAJOR}${PYTHON_VERSION_MINOR}_d.dll DESTINATION ${CURRENT_PACKAGES_DIR}/debug/bin)
+    endif()
+else()
+    vcpkg_configure_make(
+        SOURCE_PATH ${SOURCE_PATH}
+    )
+    
+    vcpkg_install_make()
+    
+    file(REMOVE_RECURSE "${CURRENT_PACKAGES_DIR}/debug/include" "${CURRENT_PACKAGES_DIR}/debug/share")
 endif()
 
 # Handle copyright
 file(COPY ${SOURCE_PATH}/LICENSE DESTINATION ${CURRENT_PACKAGES_DIR}/share/python${PYTHON_VERSION_MAJOR})
 file(RENAME ${CURRENT_PACKAGES_DIR}/share/python${PYTHON_VERSION_MAJOR}/LICENSE ${CURRENT_PACKAGES_DIR}/share/python${PYTHON_VERSION_MAJOR}/copyright)
-
-vcpkg_copy_pdbs()
diff --git a/ports/python2/vcpkg.json b/ports/python2/vcpkg.json
new file mode 100644
index 00000000000000..9780104ac1d9d5
--- /dev/null
+++ b/ports/python2/vcpkg.json
@@ -0,0 +1,7 @@
+{
+  "name": "python2",
+  "version": "2.7.18",
+  "port-version": 1,
+  "description": "The Python programming language as an embeddable library",
+  "homepage": "https://www.python.org"
+}
diff --git a/scripts/ci.baseline.txt b/scripts/ci.baseline.txt
index 5822206e2ca370..ee79031808fec9 100644
--- a/scripts/ci.baseline.txt
+++ b/scripts/ci.baseline.txt
@@ -1277,8 +1277,6 @@ protobuf-c:arm64-windows=fail
 protobuf-c:arm-uwp=fail
 python2:arm64-windows=fail
 python2:arm-uwp=fail
-python2:x64-linux=fail
-python2:x64-osx=fail
 python2:x64-uwp=fail
 qhull:x64-uwp=fail
 qhull:arm-uwp=fail
diff --git a/versions/baseline.json b/versions/baseline.json
index d6ee10fef55bde..61bf32547ec807 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -5006,7 +5006,7 @@
     },
     "python2": {
       "baseline": "2.7.18",
-      "port-version": 0
+      "port-version": 1
     },
     "python3": {
       "baseline": "3.9.5",
diff --git a/versions/p-/python2.json b/versions/p-/python2.json
index e282743223d366..95fa120883919c 100644
--- a/versions/p-/python2.json
+++ b/versions/p-/python2.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "052ef22af59535134ca2944cfd8e7e7d3ea24d67",
+      "version": "2.7.18",
+      "port-version": 1
+    },
     {
       "git-tree": "b187917ff4190f5989d395a9abe3bdae93e0ee95",
       "version-string": "2.7.18",