diff --git a/ports/pybind11/vcpkg.json b/ports/pybind11/vcpkg.json
index 3c6faa3c71..e8dbe72752 100644
--- a/ports/pybind11/vcpkg.json
+++ b/ports/pybind11/vcpkg.json
@@ -1,8 +1,10 @@
 {
   "name": "pybind11",
   "version-semver": "2.8.1",
+  "port-version": 1,
   "description": "pybind11 is a lightweight header-only library that exposes C++ types in Python and vice versa, mainly to create Python bindings of existing C++ code",
   "homepage": "https://github.com/pybind/pybind11",
+  "supports": "!(arm & windows)",
   "dependencies": [
     "python3",
     {
diff --git a/ports/python3/portfile.cmake b/ports/python3/portfile.cmake
index 758cb31720..77f8a82a83 100644
--- a/ports/python3/portfile.cmake
+++ b/ports/python3/portfile.cmake
@@ -149,7 +149,8 @@ if(VCPKG_TARGET_IS_WINDOWS OR VCPKG_TARGET_IS_UWP)
     file(GLOB PYTHON_INSTALLERS "${CURRENT_PACKAGES_DIR}/tools/${PORT}/wininst-*.exe")
     file(REMOVE ${PYTHON_LIBS} ${PYTHON_INSTALLERS})
 
-    if(PYTHON_ALLOW_EXTENSIONS)
+    # The generated python executable must match the host arch
+    if(PYTHON_ALLOW_EXTENSIONS AND NOT VCPKG_CROSSCOMPILING)
         message(STATUS "Bootstrapping pip")
         vcpkg_execute_required_process(COMMAND python -m ensurepip
             WORKING_DIRECTORY "${CURRENT_PACKAGES_DIR}/tools/${PORT}"
diff --git a/ports/python3/vcpkg.json b/ports/python3/vcpkg.json
index 2364e9fbc4..1d1b70a8e9 100644
--- a/ports/python3/vcpkg.json
+++ b/ports/python3/vcpkg.json
@@ -1,10 +1,10 @@
 {
   "name": "python3",
   "version-semver": "3.10.1",
-  "port-version": 1,
+  "port-version": 2,
   "description": "The Python programming language",
   "homepage": "https://github.com/python/cpython",
-  "supports": "!(arm | uwp)",
+  "supports": "!uwp",
   "dependencies": [
     {
       "name": "bzip2",
@@ -31,6 +31,10 @@
       "name": "openssl",
       "platform": "!(windows & static)"
     },
+    {
+      "name": "python3",
+      "host": true
+    },
     {
       "name": "sqlite3",
       "platform": "!(windows & static)"
diff --git a/versions/baseline.json b/versions/baseline.json
index b3c0fae288..9ce2849be5 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -5466,7 +5466,7 @@
     },
     "pybind11": {
       "baseline": "2.8.1",
-      "port-version": 0
+      "port-version": 1
     },
     "pystring": {
       "baseline": "1.1.3",
@@ -5478,7 +5478,7 @@
     },
     "python3": {
       "baseline": "3.10.1",
-      "port-version": 1
+      "port-version": 2
     },
     "qca": {
       "baseline": "2.3.4",
diff --git a/versions/p-/pybind11.json b/versions/p-/pybind11.json
index ee5ae11d7d..83ddc0af64 100644
--- a/versions/p-/pybind11.json
+++ b/versions/p-/pybind11.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "16618fe9543461ee68ba815f511afacbbcfd8330",
+      "version-semver": "2.8.1",
+      "port-version": 1
+    },
     {
       "git-tree": "893da2421e31681611515d8416a8f1a3b4496b5e",
       "version-semver": "2.8.1",
diff --git a/versions/p-/python3.json b/versions/p-/python3.json
index 517b8343bb..6d83a28832 100644
--- a/versions/p-/python3.json
+++ b/versions/p-/python3.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "198663bdc6b156d4423eb6ebf085c803f83babf8",
+      "version-semver": "3.10.1",
+      "port-version": 2
+    },
     {
       "git-tree": "5fe3685d04e62103465074dbe416e3158a6017a8",
       "version-semver": "3.10.1",