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 3d2fa10525..ae87a22823 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
@@ -1,3 +1,4 @@
 DIST flit_core-3.12.0-py3-none-any.whl 45594 BLAKE2B 7c6cb6eb03d45bbba27f27b3728881b57fe82dd38e03f884d3b7c46116eb2b9dd76f92bdaf7f594ef8ccbe12ec8f9a56424ff9e9fc7a839c4818a113fdf0c3d3 SHA512 790c12b1f43201e365fb3f8f2f0a54e1a578876799dfdf8bfeea679a25ea096bf62946d006618c1458ae6e37ce6d00998f37e9aba426d5ab80d32ef2d75da4e0
-DIST pip-25.2.gh.tar.gz 9121715 BLAKE2B 3bfe61d6d0d6f3a79c3fd801f5cb40b203fd12085d925ae7cde53adca3c5ee523fdfd9449546e1bc8ca719b3e8766cfef3162919e13a77f7adc0d20a951d11c7 SHA512 5cc65c9091fdda7905e26ce32ddaa3a1c2fd287d69fd3da67c814ba7e8e5be59301d8327c06cdca78c1b95f4a5b5f75c87f36a549022408cc0e8f9411c0db11e
 DIST pip-25.3.gh.tar.gz 9115712 BLAKE2B 87d848c497163a45ee3de8f6f75c80b5051b07062c5a15450ae98b59a6cebc6bf03ca8525d57929493f2cfeb28d5623401eba69f0bdfc734389efbb84eafdf53 SHA512 f50db092213ec3bb819d3da5669f73d119b5ec7f7ac5e8a587a17c27eafa32bc17a057df09389c526a3769ef3577f5553187d54ceffa89aed63f4b4498ff044e
+DIST pip-26.0.1.gh.tar.gz 9227871 BLAKE2B 96a2fab2de472b3cde570f3bcbd6bc5e5c48ef2f0808ca9b2b6c0f57a611f723cd0f5d592b6b5f553fb57a6909459f57b4130f2451cd95c3b18678e02215e0c9 SHA512 3786df7522ea65bc20fb9885ce5c2ddc60200a536a1f754a8d7dc278115c73258863e4c51ac7e9a60dda0b70263730dc194f70e1e8f8d00178a8b3c724333bf0
+DIST pip-26.0.gh.tar.gz 9226836 BLAKE2B fe24bd8fca7fa2b64ed865a880a430c420a9e73e35a9f1f2405473d4778467f48a8bc0607c1423760ff23706d3e11ddfeb20cd5a7f6522530a679994278ee1d8 SHA512 62a62b2db4e7a6c795cf01ab553b94068f0d1c62470c1f5c2b3164344a84fa68f7854eec99d93b9f56193c61276d95d8af21a3cb6b78f0db4f013d9997e78199
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-26.0.1.ebuild
similarity index 88%
rename from sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-25.2.ebuild
rename to sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-26.0.1.ebuild
index 795aa03abe..3dac603960 100644
--- 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-26.0.1.ebuild
@@ -1,14 +1,16 @@
-# Copyright 1999-2025 Gentoo Authors
+# Copyright 1999-2026 Gentoo Authors
 # Distributed under the terms of the GNU General Public License v2
 
 EAPI=8
 
-DISTUTILS_USE_PEP517=setuptools
+DISTUTILS_USE_PEP517=flit
 # PYTHON_COMPAT is used only for testing
 PYTHON_COMPAT=( pypy3_11 python3_{11..14} )
 PYTHON_REQ_USE="ssl(+),threads(+)"
 
-inherit distutils-r1
+inherit distutils-r1 pypi
+
+FLIT_CORE_PV=3.12.0
 
 MY_P=${P#ensurepip-}
 DESCRIPTION="Shared pip wheel for ensurepip Python module"
@@ -19,12 +21,15 @@ HOMEPAGE="
 "
 SRC_URI="
 	https://github.com/pypa/pip/archive/${PV}.tar.gz -> ${MY_P}.gh.tar.gz
+	test? (
+		$(pypi_wheel_url flit-core "${FLIT_CORE_PV}")
+	)
 "
 S=${WORKDIR}/${MY_P}
 
 LICENSE="MIT"
 SLOT="0"
-KEYWORDS="~alpha amd64 arm arm64 ~hppa ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 ~sparc x86 ~arm64-macos ~x64-macos ~x64-solaris"
+KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~hppa ~loong ~m68k ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~arm64-macos ~x64-macos ~x64-solaris"
 IUSE="test test-rust"
 RESTRICT="!test? ( test )"
 
@@ -78,7 +83,7 @@ python_prepare_all() {
 	local PATCHES=(
 		# remove coverage & pytest-subket wheel expectation from test suite
 		# (from dev-python/pip)
-		"${FILESDIR}/pip-25.2-test-wheels.patch"
+		"${FILESDIR}/pip-26.0-test-wheels.patch"
 	)
 
 	distutils-r1_python_prepare_all
@@ -86,6 +91,7 @@ python_prepare_all() {
 	if use test; then
 		local wheels=(
 			"${BROOT}"/usr/lib/python/ensurepip/{setuptools,wheel}-*.whl
+			"${DISTDIR}/$(pypi_wheel_name flit-core "${FLIT_CORE_PV}")"
 		)
 		mkdir tests/data/common_wheels/ || die
 		cp "${wheels[@]}" tests/data/common_wheels/ || die
@@ -151,6 +157,10 @@ python_test() {
 				# unexpected tempfiles?
 				tests/functional/test_install_config.py::test_do_not_prompt_for_authentication
 				tests/functional/test_install_config.py::test_prompt_for_authentication
+				# wrong path
+				tests/functional/test_install.py::test_install_editable_with_prefix_setup_py
+				# wrong exception assumptions
+				tests/unit/test_utils_datetime.py::test_parse_iso_datetime_invalid
 			)
 			;;
 	esac
diff --git a/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-26.0.ebuild b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-26.0.ebuild
new file mode 100644
index 0000000000..3dac603960
--- /dev/null
+++ b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/ensurepip-pip-26.0.ebuild
@@ -0,0 +1,191 @@
+# Copyright 1999-2026 Gentoo Authors
+# Distributed under the terms of the GNU General Public License v2
+
+EAPI=8
+
+DISTUTILS_USE_PEP517=flit
+# PYTHON_COMPAT is used only for testing
+PYTHON_COMPAT=( pypy3_11 python3_{11..14} )
+PYTHON_REQ_USE="ssl(+),threads(+)"
+
+inherit distutils-r1 pypi
+
+FLIT_CORE_PV=3.12.0
+
+MY_P=${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
+	test? (
+		$(pypi_wheel_url flit-core "${FLIT_CORE_PV}")
+	)
+"
+S=${WORKDIR}/${MY_P}
+
+LICENSE="MIT"
+SLOT="0"
+KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~hppa ~loong ~m68k ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~arm64-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-26.0-test-wheels.patch"
+	)
+
+	distutils-r1_python_prepare_all
+
+	if use test; then
+		local wheels=(
+			"${BROOT}"/usr/lib/python/ensurepip/{setuptools,wheel}-*.whl
+			"${DISTDIR}/$(pypi_wheel_name flit-core "${FLIT_CORE_PV}")"
+		)
+		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 ${EPYTHON} in
+		pypy3*)
+			EPYTEST_DESELECT+=(
+				# unexpected tempfiles?
+				tests/functional/test_install_config.py::test_do_not_prompt_for_authentication
+				tests/functional/test_install_config.py::test_prompt_for_authentication
+				# wrong path
+				tests/functional/test_install.py::test_install_editable_with_prefix_setup_py
+				# wrong exception assumptions
+				tests/unit/test_utils_datetime.py::test_parse_iso_datetime_invalid
+			)
+			;;
+	esac
+
+	if ! has_version "dev-python/cryptography[${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-26.0-test-wheels.patch b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/files/pip-26.0-test-wheels.patch
new file mode 100644
index 0000000000..55fb04f8f6
--- /dev/null
+++ b/sdk_container/src/third_party/portage-stable/dev-python/ensurepip-pip/files/pip-26.0-test-wheels.patch
@@ -0,0 +1,74 @@
+From f8f2b7760bfc8d64607b3bf2cdc9867fcce8276a 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 1b65e9d57..69b6f38c9 100644
+--- a/tests/conftest.py
++++ b/tests/conftest.py
+@@ -440,25 +440,6 @@ def setuptools_install(
+     return _common_wheel_editable_install(tmpdir_factory, common_wheels, "setuptools")
+ 
+ 
+-@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:
+@@ -474,8 +455,6 @@ def virtualenv_template(
+     pip_src: Path,
+     pip_editable_parts: tuple[Path, ...],
+     setuptools_install: Path,
+-    coverage_install: Path,
+-    socket_install: Path,
+ ) -> VirtualEnvironment:
+     venv_type: VirtualEnvironmentType
+     if request.config.getoption("--use-venv"):
+@@ -489,10 +468,6 @@ def virtualenv_template(
+ 
+     # Install setuptools, pytest-subket, and pip.
+     install_pth_link(venv, "setuptools", setuptools_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
+ 
+@@ -505,14 +480,6 @@ def virtualenv_template(
+     # detects changed files.
+     venv.site.joinpath("easy-install.pth").touch()
+ 
+-    if request.config.getoption("--cov"):
+-        # 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...