diff --git a/lang/python/pillow/Makefile b/lang/python/pillow/Makefile
index ad86947233d3e..e5c6e98f9d88c 100644
--- a/lang/python/pillow/Makefile
+++ b/lang/python/pillow/Makefile
@@ -7,12 +7,12 @@
 include $(TOPDIR)/rules.mk
 
 PKG_NAME:=pillow
-PKG_VERSION:=12.2.0
-PKG_RELEASE:=2
+PKG_VERSION:=12.3.0
+PKG_RELEASE:=1
 
 PYPI_NAME:=Pillow
 PYPI_SOURCE_NAME:=pillow
-PKG_HASH:=a830b1a40919539d07806aa58e1b114df53ddd43213d9c8b75847eee6c0182b5
+PKG_HASH:=3b8182a766685eaa002637e28b4ec8d6b18819a0c71f579bf0dbaa5830297cce
 
 PKG_BUILD_DEPENDS:=python-setuptools/host
 
diff --git a/lang/python/pipx/Makefile b/lang/python/pipx/Makefile
index eb6e0e4590b6a..199edd78de156 100644
--- a/lang/python/pipx/Makefile
+++ b/lang/python/pipx/Makefile
@@ -8,11 +8,11 @@
 include $(TOPDIR)/rules.mk
 
 PKG_NAME:=pipx
-PKG_VERSION:=1.13.0
+PKG_VERSION:=1.16.6
 PKG_RELEASE:=1
 
 PYPI_NAME:=pipx
-PKG_HASH:=d754c19d070893aab5d1ddb3d622ef57ec082b79f53c2664183165dbd2868c0e
+PKG_HASH:=1a2ace67be16262a3bc8d1d6eedc5d6b63119b2b9e4eadc1b280d8e9c25fd722
 
 PKG_LICENSE:=MIT
 PKG_LICENSE_FILES:=LICENSE
@@ -36,6 +36,7 @@ define Package/pipx
     +python3-urllib \
     +python3-venv \
     +python3-argcomplete \
+    +python3-filelock \
     +python3-packaging \
     +python3-platformdirs \
     +python3-userpath
diff --git a/lang/python/pipx/patches/001-drop-docutils-manpage-build.patch b/lang/python/pipx/patches/001-drop-docutils-manpage-build.patch
new file mode 100644
index 0000000000000..4af62eb95b9d6
--- /dev/null
+++ b/lang/python/pipx/patches/001-drop-docutils-manpage-build.patch
@@ -0,0 +1,36 @@
+From d1724588f0eacf71513e111ece880265231e6bb4 Mon Sep 17 00:00:00 2001
+From: Alexandru Ardelean <alex@shruggie.ro>
+Date: Tue, 11 Aug 2026 12:00:00 +0300
+Subject: [PATCH] Drop the docutils man-page build hook
+
+pipx's custom hatch build hook (hatch_build.py) unconditionally imports
+docutils to render docs/man/pipx.1.rst into a man page during the wheel
+build, pulling docutils>=0.21 into build-system.requires. OpenWrt does not
+ship the man page and has no docutils host tool, so disable the custom hook
+and drop the requirement; the CLI wheel then builds without docutils.
+
+Signed-off-by: Alexandru Ardelean <alex@shruggie.ro>
+---
+ pyproject.toml | 3 ---
+ 1 file changed, 3 deletions(-)
+
+--- a/pyproject.toml
++++ b/pyproject.toml
+@@ -1,7 +1,6 @@
+ [build-system]
+ build-backend = "hatchling.build"
+ requires = [
+-  "docutils>=0.21",
+   "hatch-vcs>=0.4",
+   "hatchling>=1.27",
+ ]
+@@ -113,9 +112,7 @@ zipapp = [
+ 
+ [tool.hatch]
+ version.source = "vcs"
+-build.hooks.custom = {}
+ build.hooks.vcs.version-file = "src/pipx/version.py"
+-build.targets.wheel.shared-data = { "build/man" = "share/man/man1" }
+ build.targets.sdist.include = [
+   "/*.md",
+   "/docs/man",
diff --git a/lang/python/pipx/test.sh b/lang/python/pipx/test.sh
new file mode 100755
index 0000000000000..37fe35c855558
--- /dev/null
+++ b/lang/python/pipx/test.sh
@@ -0,0 +1,8 @@
+#!/bin/sh
+
+[ "$1" = pipx ] || exit 0
+
+# 'pipx environment' resolves and prints pipx's path configuration with no
+# network access, proving the CLI entry point runs end-to-end.
+pipx environment >/dev/null 2>&1 || { echo "FAIL: 'pipx environment' errored"; exit 1; }
+pipx environment --value PIPX_HOME >/dev/null 2>&1 || { echo "FAIL: 'pipx environment --value' errored"; exit 1; }
diff --git a/lang/python/python-filelock/Makefile b/lang/python/python-filelock/Makefile
new file mode 100644
index 0000000000000..3e3564413ee83
--- /dev/null
+++ b/lang/python/python-filelock/Makefile
@@ -0,0 +1,42 @@
+#
+# This is free software, licensed under the GNU General Public License v2.
+# See /LICENSE for more information.
+#
+
+include $(TOPDIR)/rules.mk
+
+PKG_NAME:=python-filelock
+PKG_VERSION:=3.32.2
+PKG_RELEASE:=1
+
+PYPI_NAME:=filelock
+PKG_HASH:=c33351e1f49cae33414acbc6d56784e6ecee82514ec90795da1161fc4836b5b8
+
+PKG_LICENSE:=MIT
+PKG_LICENSE_FILES:=LICENSE
+PKG_MAINTAINER:=Alexandru Ardelean <ardeleanalex@gmail.com>
+
+PKG_BUILD_DEPENDS:=python-hatchling/host python-hatch-vcs/host
+
+include ../pypi.mk
+include $(INCLUDE_DIR)/package.mk
+include ../python3-package.mk
+
+define Package/python3-filelock
+  SECTION:=lang
+  CATEGORY:=Languages
+  SUBMENU:=Python
+  TITLE:=A platform independent file lock
+  URL:=https://github.com/tox-dev/filelock
+  DEPENDS:=+python3-light +python3-asyncio +python3-logging +python3-uuid
+endef
+
+define Package/python3-filelock/description
+A platform independent file lock that supports the with-statement and
+provides a simple way to synchronise access to a resource across
+processes and threads.
+endef
+
+$(eval $(call Py3Package,python3-filelock))
+$(eval $(call BuildPackage,python3-filelock))
+$(eval $(call BuildPackage,python3-filelock-src))
diff --git a/lang/python/python-filelock/test.sh b/lang/python/python-filelock/test.sh
new file mode 100755
index 0000000000000..fb38e58a6fed5
--- /dev/null
+++ b/lang/python/python-filelock/test.sh
@@ -0,0 +1,21 @@
+#!/bin/sh
+
+[ "$1" = python3-filelock ] || exit 0
+
+python3 - "$2" << 'EOF'
+import os
+import sys
+import tempfile
+
+import filelock
+
+# Assert the packaged version and exercise a real lock acquire/release cycle
+# through the fcntl backend, which is the code path used on the target.
+assert filelock.__version__ == sys.argv[1], (filelock.__version__, sys.argv[1])
+
+lockpath = os.path.join(tempfile.gettempdir(), "test-python3-filelock.lock")
+lock = filelock.FileLock(lockpath)
+with lock:
+    assert lock.is_locked
+assert not lock.is_locked
+EOF