diff --git a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/Manifest b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/Manifest
index 3622d339cc..86f564765d 100644
--- a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/Manifest
+++ b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/Manifest
@@ -1,2 +1,2 @@
-DIST pip-25.1.1-py3-none-any.whl 1825227 BLAKE2B 13170fa08dd26edced5e5fe8d89b38f5b3b63882489d2a951a7238f950a332ce0df11109482840595984bca187960d8fe2b7aeabfcbdaf94e5586631cc1de4e3 SHA512 e0c56f04a306cba9e13ed87f7460ad5a3bda7d6c37e05098082c58acb1f7493c8061e48df279f2c476e75d12df12d0f1a74d82e00e6fc2badffe484d281c56fc
 DIST pip-25.1.1.gh.tar.gz 9219969 BLAKE2B eb443451deeb71888c2fc56ac5c8cb2d0515ec0efff975fab98cfa65d1fc5e66948243b3acebf1f4b0446e46082abb9fd350816579a4f5af1292c160490ce930 SHA512 ce61c9861265139b3c5ea9be9dc246097cd75c21687cf8301f80a377d02420c4524f0d6307d2ca0232ff8715b1105343bcfdb9cac6b69503780ab2c4645558dc
+DIST pip-25.2.gh.tar.gz 9121715 BLAKE2B 3bfe61d6d0d6f3a79c3fd801f5cb40b203fd12085d925ae7cde53adca3c5ee523fdfd9449546e1bc8ca719b3e8766cfef3162919e13a77f7adc0d20a951d11c7 SHA512 5cc65c9091fdda7905e26ce32ddaa3a1c2fd287d69fd3da67c814ba7e8e5be59301d8327c06cdca78c1b95f4a5b5f75c87f36a549022408cc0e8f9411c0db11e
diff --git a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.1.1-r1.ebuild b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.1.1-r1.ebuild
index bf8abb5972..6aa83df377 100644
--- a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.1.1-r1.ebuild
+++ b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.1.1-r1.ebuild
@@ -24,7 +24,7 @@ S=${WORKDIR}/${MY_P}
 
 LICENSE="MIT"
 SLOT="0"
-KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~hppa ~loong ~m68k ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~amd64-linux ~x86-linux ~arm64-macos ~ppc-macos ~x64-macos ~x64-solaris"
+KEYWORDS="~alpha amd64 arm arm64 hppa ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~amd64-linux ~x86-linux ~arm64-macos ~ppc-macos ~x64-macos ~x64-solaris"
 IUSE="test test-rust"
 RESTRICT="!test? ( test )"
 
diff --git a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.1.1.ebuild b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.1.1.ebuild
deleted file mode 100644
index 23904e1f43..0000000000
--- a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.1.1.ebuild
+++ /dev/null
@@ -1,20 +0,0 @@
-# Copyright 2022-2025 Gentoo Authors
-# Distributed under the terms of the GNU General Public License v2
-
-EAPI=8
-
-inherit pypi
-
-DESCRIPTION="Shared pip wheel for ensurepip Python module"
-HOMEPAGE="https://pypi.org/project/pip/"
-SRC_URI="$(pypi_wheel_url "${PN#ensurepip-}")"
-S=${DISTDIR}
-
-LICENSE="Apache-2.0 BSD BSD-2 ISC LGPL-2.1+ MIT MPL-2.0 PSF-2"
-SLOT="0"
-KEYWORDS="~alpha amd64 arm arm64 hppa ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~amd64-linux ~x86-linux ~arm64-macos ~ppc-macos ~x64-macos ~x64-solaris"
-
-src_install() {
-	insinto /usr/lib/python/ensurepip
-	doins "${A}"
-}
diff --git a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.2.ebuild b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.2.ebuild
new file mode 100644
index 0000000000..93cadffb58
--- /dev/null
+++ b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.2.ebuild
@@ -0,0 +1,181 @@
+# Copyright 1999-2025 Gentoo Authors
+# Distributed under the terms of the GNU General Public License v2
+
+EAPI=8
+
+DISTUTILS_USE_PEP517=setuptools
+# PYTHON_COMPAT is used only for testing
+PYTHON_COMPAT=( pypy3_11 python3_{11..14} )
+PYTHON_REQ_USE="ssl(+),threads(+)"
+
+inherit distutils-r1
+
+MY_P=${P#ensurepip-}
+DESCRIPTION="Shared pip wheel for ensurepip Python module"
+HOMEPAGE="
+	https://pip.pypa.io/en/stable/
+	https://pypi.org/project/pip/
+	https://github.com/pypa/pip/
+"
+SRC_URI="
+	https://github.com/pypa/pip/archive/${PV}.tar.gz -> ${MY_P}.gh.tar.gz
+"
+S=${WORKDIR}/${MY_P}
+
+LICENSE="MIT"
+SLOT="0"
+KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~hppa ~loong ~m68k ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~amd64-linux ~x86-linux ~arm64-macos ~ppc-macos ~x64-macos ~x64-solaris"
+IUSE="test test-rust"
+RESTRICT="!test? ( test )"
+
+BDEPEND="
+	${RDEPEND}
+	test? (
+		<dev-python/ensurepip-setuptools-80
+		dev-python/ensurepip-wheel
+		dev-python/freezegun[${PYTHON_USEDEP}]
+		dev-python/pretend[${PYTHON_USEDEP}]
+		dev-python/scripttest[${PYTHON_USEDEP}]
+		dev-python/virtualenv[${PYTHON_USEDEP}]
+		dev-python/werkzeug[${PYTHON_USEDEP}]
+		dev-python/wheel[${PYTHON_USEDEP}]
+		test-rust? (
+			dev-python/cryptography[${PYTHON_USEDEP}]
+		)
+		dev-vcs/git
+	)
+"
+
+EPYTEST_PLUGINS=()
+EPYTEST_RERUNS=5
+EPYTEST_XDIST=1
+distutils_enable_tests pytest
+
+declare -A VENDOR_LICENSES=(
+	[cachecontrol]=Apache-2.0
+	[certifi]=MPL-2.0
+	[dependency_groups]=MIT
+	[distlib]=PSF-2
+	[distro]=Apache-2.0
+	[idna]=BSD
+	[msgpack]=Apache-2.0
+	[packaging]="|| ( Apache-2.0 MIT )"
+	[pkg_resources]=MIT
+	[platformdirs]=MIT
+	[pygments]=BSD-2
+	[pyproject_hooks]=MIT
+	[requests]=Apache-2.0
+	[resolvelib]=ISC
+	[rich]=MIT
+	[tomli]=MIT
+	[tomli_w]=MIT
+	[truststore]=MIT
+	[urllib3]=MIT
+)
+LICENSE+=" ${VENDOR_LICENSES[*]}"
+
+python_prepare_all() {
+	local PATCHES=(
+		# remove coverage & pytest-subket wheel expectation from test suite
+		# (from dev-python/pip)
+		"${FILESDIR}/pip-25.2-test-wheels.patch"
+	)
+
+	distutils-r1_python_prepare_all
+
+	if use test; then
+		local wheels=(
+			"${BROOT}"/usr/lib/python/ensurepip/{setuptools,wheel}-*.whl
+		)
+		mkdir tests/data/common_wheels/ || die
+		cp "${wheels[@]}" tests/data/common_wheels/ || die
+	fi
+
+	# Verify that we've covered licenses for all vendored packages
+	cd src/pip/_vendor || die
+	local packages=( */ )
+	local pkg missing=()
+	for pkg in "${packages[@]%/}"; do
+		if [[ ! -v "VENDOR_LICENSES[${pkg}]" ]]; then
+			missing+=( "${pkg}" )
+		else
+			unset "VENDOR_LICENSES[${pkg}]"
+		fi
+	done
+
+	if [[ ${missing[@]} || ${VENDOR_LICENSES[@]} ]]; then
+		[[ ${missing[@]} ]] &&
+			eerror "License missing for packages: ${missing[*]}"
+		[[ ${VENDOR_LICENSES[@]} ]] &&
+			eerror "Vendored packages removed: ${!VENDOR_LICENSES[*]}"
+		die "VENDOR_LICENSES outdated"
+	fi
+
+	local upstream_count=$(wc -l < vendor.txt || die)
+	if [[ ${#packages[@]} -ne ${upstream_count} ]]; then
+		eerror "VENDOR_LICENSES: ${#packages[@]}"
+		eerror "vendor.txt:      ${upstream_count}"
+		die "Not all vendored packages matched"
+	fi
+}
+
+python_test() {
+	local EPYTEST_DESELECT=(
+		tests/functional/test_inspect.py::test_inspect_basic
+		# Internet
+		tests/functional/test_config_settings.py::test_backend_sees_config_via_sdist
+		tests/functional/test_install.py::test_double_install_fail
+		tests/functional/test_install.py::test_install_sdist_links
+		tests/functional/test_install_config.py::test_prompt_for_keyring_if_needed
+		tests/functional/test_lock.py::test_lock_archive
+		tests/functional/test_lock.py::test_lock_vcs
+		# broken by system site-packages use
+		tests/functional/test_freeze.py::test_freeze_with_setuptools
+		tests/functional/test_pip_runner_script.py::test_runner_work_in_environments_with_no_pip
+		tests/functional/test_uninstall.py::test_basic_uninstall_distutils
+		tests/unit/test_base_command.py::test_base_command_global_tempdir_cleanup
+		tests/unit/test_base_command.py::test_base_command_local_tempdir_cleanup
+		tests/unit/test_base_command.py::test_base_command_provides_tempdir_helpers
+	)
+	local EPYTEST_IGNORE=(
+		# from upstream options
+		src/pip/_vendor
+		tests/tests_cache
+		# requires proxy.py
+		tests/functional/test_proxy.py
+	)
+
+	case ${EPYTHON} in
+		pypy3*)
+			EPYTEST_DESELECT+=(
+				# unexpected tempfiles?
+				tests/functional/test_install_config.py::test_do_not_prompt_for_authentication
+				tests/functional/test_install_config.py::test_prompt_for_authentication
+			)
+			;;
+	esac
+
+	if ! has_version "dev-python/cryptography[${PYTHON_USEDEP}]"; then
+		EPYTEST_DESELECT+=(
+			tests/functional/test_install.py::test_install_sends_client_cert
+			tests/functional/test_install_config.py::test_do_not_prompt_for_authentication
+			tests/functional/test_install_config.py::test_prompt_for_authentication
+			tests/functional/test_install_config.py::test_prompt_for_keyring_if_needed
+		)
+	fi
+
+	local -x PIP_DISABLE_PIP_VERSION_CHECK=1
+	# rerunfailures because test suite breaks if packages are installed
+	# in parallel
+	epytest -m "not network" -o addopts= -o tmp_path_retention_policy=all \
+		--use-venv
+}
+
+src_install() {
+	if [[ ${DISTUTILS_WHEEL_PATH} != *py3-none-any.whl ]]; then
+		die "Non-pure wheel produced?! ${DISTUTILS_WHEEL_PATH}"
+	fi
+	# TODO: compress it?
+	insinto /usr/lib/python/ensurepip
+	doins "${DISTUTILS_WHEEL_PATH}"
+}
diff --git a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/files/pip-25.2-test-wheels.patch b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/files/pip-25.2-test-wheels.patch
new file mode 100644
index 0000000000..c99af85681
--- /dev/null
+++ b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/files/pip-25.2-test-wheels.patch
@@ -0,0 +1,74 @@
+From f172db76c62cf8e00fb547828c43cd8bf78a31ef Mon Sep 17 00:00:00 2001
+From: =?UTF-8?q?Micha=C5=82=20G=C3=B3rny?= <mgorny@gentoo.org>
+Date: Thu, 31 Jul 2025 05:10:08 +0200
+Subject: [PATCH] Disable coverage & socket plugins inside test venvs
+
+---
+ tests/conftest.py | 33 ---------------------------------
+ 1 file changed, 33 deletions(-)
+
+diff --git a/tests/conftest.py b/tests/conftest.py
+index c98b87117..f4ef35a7e 100644
+--- a/tests/conftest.py
++++ b/tests/conftest.py
+@@ -444,25 +444,6 @@ def wheel_install(tmpdir_factory: pytest.TempPathFactory, common_wheels: Path) -
+     return _common_wheel_editable_install(tmpdir_factory, common_wheels, "wheel")
+ 
+ 
+-@pytest.fixture(scope="session")
+-def coverage_install(
+-    tmpdir_factory: pytest.TempPathFactory, common_wheels: Path
+-) -> Path:
+-    return _common_wheel_editable_install(tmpdir_factory, common_wheels, "coverage")
+-
+-
+-@pytest.fixture(scope="session")
+-def socket_install(tmpdir_factory: pytest.TempPathFactory, common_wheels: Path) -> Path:
+-    lib_dir = _common_wheel_editable_install(
+-        tmpdir_factory, common_wheels, "pytest_subket"
+-    )
+-    # pytest-subket is only included so it can intercept and block unexpected
+-    # network requests. It should NOT be visible to the pip under test.
+-    dist_info = next(lib_dir.glob("*.dist-info"))
+-    shutil.rmtree(dist_info)
+-    return lib_dir
+-
+-
+ def install_pth_link(
+     venv: VirtualEnvironment, project_name: str, lib_dir: Path
+ ) -> None:
+@@ -479,8 +460,6 @@ def virtualenv_template(
+     pip_editable_parts: tuple[Path, ...],
+     setuptools_install: Path,
+     wheel_install: Path,
+-    coverage_install: Path,
+-    socket_install: Path,
+ ) -> VirtualEnvironment:
+     venv_type: VirtualEnvironmentType
+     if request.config.getoption("--use-venv"):
+@@ -494,11 +473,7 @@ def virtualenv_template(
+ 
+     # Install setuptools, wheel, pytest-subket, and pip.
+     install_pth_link(venv, "setuptools", setuptools_install)
+     install_pth_link(venv, "wheel", wheel_install)
+-    install_pth_link(venv, "pytest_subket", socket_install)
+-    # Also copy pytest-subket's .pth file so it can intercept socket calls.
+-    with open(venv.site / "pytest_socket.pth", "w") as f:
+-        f.write(socket_install.joinpath("pytest_socket.pth").read_text())
+ 
+     pth, dist_info = pip_editable_parts
+ 
+@@ -511,13 +485,6 @@ def virtualenv_template(
+     # detects changed files.
+     venv.site.joinpath("easy-install.pth").touch()
+ 
+-    # Install coverage and pth file for executing it in any spawned processes
+-    # in this virtual environment.
+-    install_pth_link(venv, "coverage", coverage_install)
+-    # zz prefix ensures the file is after easy-install.pth.
+-    with open(venv.site / "zz-coverage-helper.pth", "a") as f:
+-        f.write("import coverage; coverage.process_startup()")
+-
+     # Drop (non-relocatable) launchers.
+     for exe in os.listdir(venv.bin):
+         if not exe.startswith(("python", "libpy")):  # Don't remove libpypy-c.so...