diff --git a/sdk_container/src/third_party/portage-stable/dev-python/pip/Manifest b/sdk_container/src/third_party/portage-stable/dev-python/pip/Manifest
index 5b892dfc3c..91bf1f520d 100644
--- a/sdk_container/src/third_party/portage-stable/dev-python/pip/Manifest
+++ b/sdk_container/src/third_party/portage-stable/dev-python/pip/Manifest
@@ -1,3 +1,4 @@
 DIST pip-24.1.gh.tar.gz 9188658 BLAKE2B 4a43ff0199d811dd30461e376f655a447f3f706a48dd97fe1d0ccf630f558e72209ccd06d98949a1541cd6b2942a816db23ce8aaa7fbbf9aef429502fb91ab92 SHA512 c60ab329fe91202ff64b5f0f90209085fbf8db0f0a05f0703f952ad69e39e2e3edb5dadc006a3f317cdd4ba4fb5abe56dfbd22792249a2d139702eec272186d1
 DIST pip-25.0.1.gh.tar.gz 9224526 BLAKE2B db729b8c75d8e15c6fed1dbc9e08adc4e82114f2bbd953859ec03c7948e521629afd8cea6adb08110b987d6adf48fd600a59a3bcc27774db61ea92675ad90d42 SHA512 a6850c8567082bbf98483a45e523c4de12132136d2b0aa388ac619c02ffd0c8f6aea7d727f7d84167dadec5f1e56dd478b2233b0caa5d9b3e5cadc9e1f3dc12c
+DIST pip-25.1.1.gh.tar.gz 9219969 BLAKE2B eb443451deeb71888c2fc56ac5c8cb2d0515ec0efff975fab98cfa65d1fc5e66948243b3acebf1f4b0446e46082abb9fd350816579a4f5af1292c160490ce930 SHA512 ce61c9861265139b3c5ea9be9dc246097cd75c21687cf8301f80a377d02420c4524f0d6307d2ca0232ff8715b1105343bcfdb9cac6b69503780ab2c4645558dc
 DIST pip-25.1.gh.tar.gz 9220205 BLAKE2B 3e719b180dd4f039a1bf15cdd2686fdc270e842e4b9ab416306bf9ea40c037541df05af78239fe067dfa3edc27b7370ea04c1d9cec43cc6cfd2f9e8f347f41ee SHA512 d6b93aeabe6a4e046caf85c028fca380936ab65cb3c5028a7fa7dbc61cef2cf7d0c46c499fe548dc0af8f7bc30f7ecace8f257b20a60c0cc905b531f193b5a9d
diff --git a/sdk_container/src/third_party/portage-stable/dev-python/pip/files/pip-25.1-tomli-dep.patch b/sdk_container/src/third_party/portage-stable/dev-python/pip/files/pip-25.1-tomli-dep.patch
new file mode 100644
index 0000000000..780d9a84ad
--- /dev/null
+++ b/sdk_container/src/third_party/portage-stable/dev-python/pip/files/pip-25.1-tomli-dep.patch
@@ -0,0 +1,76 @@
+From 23d20ea18ab4e43a4a4cb2b721d818a8dcd62542 Mon Sep 17 00:00:00 2001
+From: Eli Schwartz <eschwartz93@gmail.com>
+Date: Mon, 28 Apr 2025 11:42:02 -0400
+Subject: [PATCH] Fix new dependency-groups feature to use the stdlib tomllib
+ where possible
+
+Previously, commit 88c9f31ad8a5ffe0bb31ab500b8ddd1b9ff6a5dd modified pip
+to use the stdlib on versions of python where this module is in the
+stdlib. As justified there:
+
+Although a tomli copy is vendored, doing this conditional import allows:
+- automatically upgrading the code, when the time comes to drop py3.10
+  support
+
+- slightly simplifying debundling support, as it's no longer necessary
+  to depend on a tomli(-wheel)? package on sufficiently newer versions
+  of python.
+
+https://github.com/pypa/pip/pull/13065 added a new feature, including a
+vendored "dependency_groups" library that likewise supports using the
+stdlib tomllib via `dependency_groups/_toml_compat.py`. But the code in
+pip itself to use dependency_groups manually loads pyproject.toml and
+passes it to dependency_groups, and fails to use the same compatibility
+dispatch as both the pre-existing pip code and dependency_groups itself.
+
+Add back the conditional logic.
+---
+ news/13356.vendor.rst                         |  1 +
+ src/pip/_internal/req/req_dependency_group.py | 11 ++++++++---
+ tests/unit/test_req_dependency_group.py       |  2 +-
+ 3 files changed, 10 insertions(+), 4 deletions(-)
+ create mode 100644 news/13356.vendor.rst
+
+diff --git a/src/pip/_internal/req/req_dependency_group.py b/src/pip/_internal/req/req_dependency_group.py
+index 8f124de5b81..e81dd45522a 100644
+--- a/src/pip/_internal/req/req_dependency_group.py
++++ b/src/pip/_internal/req/req_dependency_group.py
+@@ -1,6 +1,11 @@
++import sys
+ from typing import Any, Dict, Iterable, Iterator, List, Tuple
+ 
+-from pip._vendor import tomli
++if sys.version_info >= (3, 11):
++    import tomllib
++else:
++    from pip._vendor import tomli as tomllib
++
+ from pip._vendor.dependency_groups import DependencyGroupResolver
+ 
+ from pip._internal.exceptions import InstallationError
+@@ -65,10 +70,10 @@ def _load_pyproject(path: str) -> Dict[str, Any]:
+     """
+     try:
+         with open(path, "rb") as fp:
+-            return tomli.load(fp)
++            return tomllib.load(fp)
+     except FileNotFoundError:
+         raise InstallationError(f"{path} not found. Cannot resolve '--group' option.")
+-    except tomli.TOMLDecodeError as e:
++    except tomllib.TOMLDecodeError as e:
+         raise InstallationError(f"Error parsing {path}: {e}") from e
+     except OSError as e:
+         raise InstallationError(f"Error reading {path}: {e}") from e
+diff --git a/tests/unit/test_req_dependency_group.py b/tests/unit/test_req_dependency_group.py
+index b596f6fc5d7..1b180f8d7f8 100644
+--- a/tests/unit/test_req_dependency_group.py
++++ b/tests/unit/test_req_dependency_group.py
+@@ -120,7 +120,7 @@ def epipe_toml_load(*args: Any, **kwargs: Any) -> None:
+         raise OSError(errno.EPIPE, "Broken pipe")
+ 
+     monkeypatch.setattr(
+-        "pip._internal.req.req_dependency_group.tomli.load", epipe_toml_load
++        "pip._internal.req.req_dependency_group.tomllib.load", epipe_toml_load
+     )
+ 
+     with pytest.raises(InstallationError, match=r"Error reading pyproject\.toml"):
diff --git a/sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1.ebuild b/sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1-r1.ebuild
similarity index 98%
rename from sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1.ebuild
rename to sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1-r1.ebuild
index 0ae9fd71e7..f85c41d9f5 100644
--- a/sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1.ebuild
+++ b/sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1-r1.ebuild
@@ -53,7 +53,7 @@ BDEPEND="
 	test? (
 		$(python_gen_cond_dep '
 			dev-python/ensurepip-setuptools
-			<dev-python/ensurepip-wheel-0.46
+			dev-python/ensurepip-wheel
 			dev-python/freezegun[${PYTHON_USEDEP}]
 			dev-python/pretend[${PYTHON_USEDEP}]
 			dev-python/pytest-rerunfailures[${PYTHON_USEDEP}]
@@ -78,6 +78,8 @@ python_prepare_all() {
 		"${FILESDIR}/pip-23.1-no-coverage.patch"
 		# prepare to unbundle dependencies
 		"${FILESDIR}/pip-25.0.1-unbundle.patch"
+		# https://github.com/pypa/pip/pull/13356
+		"${FILESDIR}/${P}-tomli-dep.patch"
 	)
 
 	distutils-r1_python_prepare_all
diff --git a/sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1.1.ebuild b/sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1.1.ebuild
new file mode 100644
index 0000000000..e669ddb4d7
--- /dev/null
+++ b/sdk_container/src/third_party/portage-stable/dev-python/pip/pip-25.1.1.ebuild
@@ -0,0 +1,181 @@
+# Copyright 1999-2025 Gentoo Authors
+# Distributed under the terms of the GNU General Public License v2
+
+EAPI=8
+
+# please bump dev-python/ensurepip-pip along with this package!
+
+DISTUTILS_USE_PEP517=setuptools
+PYTHON_TESTED=( pypy3_11 python3_{11..13} )
+PYTHON_COMPAT=( "${PYTHON_TESTED[@]}" )
+PYTHON_REQ_USE="ssl(+),threads(+)"
+
+inherit distutils-r1 shell-completion
+
+DESCRIPTION="The PyPA recommended tool for installing Python packages"
+HOMEPAGE="
+	https://pip.pypa.io/en/stable/
+	https://pypi.org/project/pip/
+	https://github.com/pypa/pip/
+"
+SRC_URI="
+	https://github.com/pypa/pip/archive/${PV}.tar.gz -> ${P}.gh.tar.gz
+"
+
+LICENSE="MIT"
+SLOT="0"
+KEYWORDS="~amd64 ~mips ~ppc ~riscv ~x86"
+IUSE="test-rust"
+
+# see src/pip/_vendor/vendor.txt
+RDEPEND="
+	>=dev-python/cachecontrol-0.14.2[${PYTHON_USEDEP}]
+	>=dev-python/dependency-groups-1.3.0[${PYTHON_USEDEP}]
+	>=dev-python/distlib-0.3.9[${PYTHON_USEDEP}]
+	>=dev-python/distro-1.9.0[${PYTHON_USEDEP}]
+	>=dev-python/msgpack-1.1.0[${PYTHON_USEDEP}]
+	>=dev-python/packaging-25.0[${PYTHON_USEDEP}]
+	>=dev-python/platformdirs-4.3.7[${PYTHON_USEDEP}]
+	>=dev-python/pyproject-hooks-1.2.0[${PYTHON_USEDEP}]
+	>=dev-python/requests-2.32.3[${PYTHON_USEDEP}]
+	>=dev-python/rich-14.0.0[${PYTHON_USEDEP}]
+	>=dev-python/resolvelib-1.1.0[${PYTHON_USEDEP}]
+	>=dev-python/setuptools-70.3.0[${PYTHON_USEDEP}]
+	>=dev-python/tomli-w-1.2.0[${PYTHON_USEDEP}]
+	>=dev-python/truststore-0.10.1[${PYTHON_USEDEP}]
+	>=dev-python/typing-extensions-4.13.2[${PYTHON_USEDEP}]
+"
+BDEPEND="
+	${RDEPEND}
+	test? (
+		$(python_gen_cond_dep '
+			dev-python/ensurepip-setuptools
+			dev-python/ensurepip-wheel
+			dev-python/freezegun[${PYTHON_USEDEP}]
+			dev-python/pretend[${PYTHON_USEDEP}]
+			dev-python/pytest-rerunfailures[${PYTHON_USEDEP}]
+			dev-python/pytest-xdist[${PYTHON_USEDEP}]
+			dev-python/scripttest[${PYTHON_USEDEP}]
+			<dev-python/setuptools-80[${PYTHON_USEDEP}]
+			dev-python/virtualenv[${PYTHON_USEDEP}]
+			dev-python/werkzeug[${PYTHON_USEDEP}]
+			dev-python/wheel[${PYTHON_USEDEP}]
+			test-rust? (
+				dev-python/cryptography[${PYTHON_USEDEP}]
+			)
+			dev-vcs/git
+		' "${PYTHON_TESTED[@]}")
+	)
+"
+
+distutils_enable_tests pytest
+
+python_prepare_all() {
+	local PATCHES=(
+		"${FILESDIR}/pip-23.1-no-coverage.patch"
+		# prepare to unbundle dependencies
+		"${FILESDIR}/pip-25.0.1-unbundle.patch"
+	)
+
+	distutils-r1_python_prepare_all
+
+	# unbundle dependencies
+	rm -r src/pip/_vendor || die
+	find -name '*.py' -exec sed -i \
+		-e 's:from pip\._vendor import:import:g' \
+		-e 's:from pip\._vendor\.:from :g' \
+		{} + || die
+
+	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
+}
+
+python_configure() {
+	if use test && has_version "dev-python/pip[${PYTHON_USEDEP}]"; then
+		"${EPYTHON}" -m pip check ||
+			die "${EPYTHON} -m pip check failed, tests will fail"
+	fi
+}
+
+python_compile_all() {
+	# 'pip completion' command embeds full $0 into completion script, which confuses
+	# 'complete' and causes QA warning when running as "${PYTHON} -m pip".
+	# This trick sets correct $0 while still calling just installed pip.
+	local pipcmd='import sys; sys.argv[0] = "pip"; __file__ = ""; from pip._internal.cli.main import main; sys.exit(main())'
+	"${EPYTHON}" -c "${pipcmd}" completion --bash > completion.bash || die
+	"${EPYTHON}" -c "${pipcmd}" completion --zsh > completion.zsh || die
+}
+
+python_test() {
+	if ! has "${EPYTHON}" "${PYTHON_TESTED[@]/_/.}"; then
+		einfo "Skipping tests on ${EPYTHON}"
+		return 0
+	fi
+
+	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
+		# broken by unbundling
+		"tests/functional/test_debug.py::test_debug[vendored library versions:]"
+		tests/functional/test_debug.py::test_debug__library_versions
+		tests/functional/test_python_option.py::test_python_interpreter
+		tests/functional/test_uninstall.py::test_uninstall_non_local_distutils
+	)
+	local EPYTEST_IGNORE=(
+		# 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
+	local -x PYTEST_DISABLE_PLUGIN_AUTOLOAD=1
+	local EPYTEST_XDIST=1
+	# rerunfailures because test suite breaks if packages are installed
+	# in parallel
+	epytest -m "not network" -o tmp_path_retention_policy=all \
+		-p rerunfailures --reruns=5 --use-venv
+}
+
+python_install_all() {
+	local DOCS=( AUTHORS.txt docs/html/**/*.rst )
+	distutils-r1_python_install_all
+
+	newbashcomp completion.bash pip
+	newzshcomp completion.zsh _pip
+}