diff --git a/dev-libs/libsodium/libsodium-1.0.18_p20220618.ebuild b/dev-libs/libsodium/libsodium-1.0.18_p20220618.ebuild
index 74d3824a82caf..e98b55fa65ca1 100644
--- a/dev-libs/libsodium/libsodium-1.0.18_p20220618.ebuild
+++ b/dev-libs/libsodium/libsodium-1.0.18_p20220618.ebuild
@@ -1,4 +1,4 @@
-# Copyright 1999-2022 Gentoo Authors
+# Copyright 1999-2023 Gentoo Authors
 # Distributed under the terms of the GNU General Public License v2
 
 EAPI=8
@@ -31,7 +31,7 @@ fi
 
 LICENSE="ISC"
 SLOT="0/23"
-KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 IUSE="+asm minimal static-libs +urandom"
 
 CPU_USE=( cpu_flags_x86_{aes,sse4_1} )
diff --git a/dev-python/asttokens/asttokens-2.2.1.ebuild b/dev-python/asttokens/asttokens-2.2.1.ebuild
index e72d38a19163e..2a1d475261831 100644
--- a/dev-python/asttokens/asttokens-2.2.1.ebuild
+++ b/dev-python/asttokens/asttokens-2.2.1.ebuild
@@ -20,7 +20,7 @@ SRC_URI="
 
 LICENSE="Apache-2.0"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	dev-python/six[${PYTHON_USEDEP}]
diff --git a/dev-python/backcall/backcall-0.2.0-r1.ebuild b/dev-python/backcall/backcall-0.2.0-r1.ebuild
index a2a882bb382ce..83481a615348c 100644
--- a/dev-python/backcall/backcall-0.2.0-r1.ebuild
+++ b/dev-python/backcall/backcall-0.2.0-r1.ebuild
@@ -13,6 +13,6 @@ HOMEPAGE="https://pypi.org/project/backcall/"
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~amd64-linux ~x86-linux"
+KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~amd64-linux ~x86-linux ~arm64-macos ~x64-macos"
 
 distutils_enable_tests pytest
diff --git a/dev-python/comm/comm-0.1.4.ebuild b/dev-python/comm/comm-0.1.4.ebuild
index d7f404401a5b9..c656e0b0741cd 100644
--- a/dev-python/comm/comm-0.1.4.ebuild
+++ b/dev-python/comm/comm-0.1.4.ebuild
@@ -21,7 +21,7 @@ SRC_URI="
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86"
+KEYWORDS="~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	>=dev-python/traitlets-4[${PYTHON_USEDEP}]
diff --git a/dev-python/executing/executing-1.2.0.ebuild b/dev-python/executing/executing-1.2.0.ebuild
index ce710a680b92d..5079c38a00f88 100644
--- a/dev-python/executing/executing-1.2.0.ebuild
+++ b/dev-python/executing/executing-1.2.0.ebuild
@@ -20,7 +20,7 @@ SRC_URI="
 
 LICENSE="MIT"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 BDEPEND="
 	dev-python/setuptools-scm[${PYTHON_USEDEP}]
diff --git a/dev-python/ipykernel/ipykernel-6.25.1.ebuild b/dev-python/ipykernel/ipykernel-6.25.1-r1.ebuild
similarity index 95%
rename from dev-python/ipykernel/ipykernel-6.25.1.ebuild
rename to dev-python/ipykernel/ipykernel-6.25.1-r1.ebuild
index 37ffb104142bb..bac003cd898d0 100644
--- a/dev-python/ipykernel/ipykernel-6.25.1.ebuild
+++ b/dev-python/ipykernel/ipykernel-6.25.1-r1.ebuild
@@ -17,11 +17,11 @@ HOMEPAGE="
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86"
+KEYWORDS="~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	>=dev-python/comm-0.1.1[${PYTHON_USEDEP}]
-	>=dev-python/debugpy-1.6.5[${PYTHON_USEDEP}]
+	!elibc_Darwin? ( >=dev-python/debugpy-1.6.5[${PYTHON_USEDEP}] )
 	>=dev-python/ipython-7.23.1[${PYTHON_USEDEP}]
 	>=dev-python/jupyter-client-8[${PYTHON_USEDEP}]
 	>=dev-python/jupyter-core-4.12[${PYTHON_USEDEP}]
diff --git a/dev-python/ipython/ipython-8.14.0.ebuild b/dev-python/ipython/ipython-8.14.0.ebuild
index d5d6ce1849502..078e82f3a81f6 100644
--- a/dev-python/ipython/ipython-8.14.0.ebuild
+++ b/dev-python/ipython/ipython-8.14.0.ebuild
@@ -18,7 +18,7 @@ HOMEPAGE="
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 IUSE="doc examples notebook nbconvert qt5 +smp test"
 RESTRICT="!test? ( test )"
 
diff --git a/dev-python/jedi/jedi-0.19.0.ebuild b/dev-python/jedi/jedi-0.19.0.ebuild
index 62299e208df76..e59be45a211be 100644
--- a/dev-python/jedi/jedi-0.19.0.ebuild
+++ b/dev-python/jedi/jedi-0.19.0.ebuild
@@ -30,7 +30,7 @@ LICENSE="
 	test? ( Apache-2.0 )
 "
 SLOT="0"
-KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86"
+KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	<dev-python/parso-0.9[${PYTHON_USEDEP}]
diff --git a/dev-python/jupyter-client/jupyter-client-8.3.0.ebuild b/dev-python/jupyter-client/jupyter-client-8.3.0.ebuild
index 185bdd906119a..33b3a44b6cbfc 100644
--- a/dev-python/jupyter-client/jupyter-client-8.3.0.ebuild
+++ b/dev-python/jupyter-client/jupyter-client-8.3.0.ebuild
@@ -18,7 +18,7 @@ HOMEPAGE="
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	>=dev-python/jupyter-core-5.1[${PYTHON_USEDEP}]
diff --git a/dev-python/jupyter-core/jupyter-core-5.3.1.ebuild b/dev-python/jupyter-core/jupyter-core-5.3.1.ebuild
index ebf39ed57a8be..1f8618452473a 100644
--- a/dev-python/jupyter-core/jupyter-core-5.3.1.ebuild
+++ b/dev-python/jupyter-core/jupyter-core-5.3.1.ebuild
@@ -17,7 +17,7 @@ HOMEPAGE="
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	>=dev-python/platformdirs-2.5[${PYTHON_USEDEP}]
diff --git a/dev-python/matplotlib-inline/matplotlib-inline-0.1.6.ebuild b/dev-python/matplotlib-inline/matplotlib-inline-0.1.6.ebuild
index 8c018782fd1f0..8f5fe6dcea764 100644
--- a/dev-python/matplotlib-inline/matplotlib-inline-0.1.6.ebuild
+++ b/dev-python/matplotlib-inline/matplotlib-inline-0.1.6.ebuild
@@ -17,7 +17,7 @@ SRC_URI="
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	dev-python/matplotlib[${PYTHON_USEDEP}]
diff --git a/dev-python/nest-asyncio/nest-asyncio-1.5.7.ebuild b/dev-python/nest-asyncio/nest-asyncio-1.5.7.ebuild
index 42f6ac1eea82b..d8eafbe56995b 100644
--- a/dev-python/nest-asyncio/nest-asyncio-1.5.7.ebuild
+++ b/dev-python/nest-asyncio/nest-asyncio-1.5.7.ebuild
@@ -16,6 +16,6 @@ HOMEPAGE="
 
 LICENSE="BSD-2"
 SLOT="0"
-KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~m68k ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86"
+KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~m68k ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~arm64-macos ~x64-macos"
 
 distutils_enable_tests pytest
diff --git a/dev-python/parso/parso-0.8.3-r1.ebuild b/dev-python/parso/parso-0.8.3-r1.ebuild
index 0bfdc9d8a1eb0..1e3d469f7c670 100644
--- a/dev-python/parso/parso-0.8.3-r1.ebuild
+++ b/dev-python/parso/parso-0.8.3-r1.ebuild
@@ -20,7 +20,7 @@ SRC_URI="
 
 LICENSE="MIT"
 SLOT="0"
-KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 distutils_enable_sphinx docs
 distutils_enable_tests pytest
diff --git a/dev-python/pickleshare/pickleshare-0.7.5.ebuild b/dev-python/pickleshare/pickleshare-0.7.5.ebuild
index b06730508ac36..18d1dd467c34a 100644
--- a/dev-python/pickleshare/pickleshare-0.7.5.ebuild
+++ b/dev-python/pickleshare/pickleshare-0.7.5.ebuild
@@ -10,7 +10,7 @@ HOMEPAGE="https://github.com/pickleshare/pickleshare"
 
 LICENSE="MIT"
 SLOT="0"
-KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	>=dev-python/path-6.2[${PYTHON_USEDEP}]"
diff --git a/dev-python/prompt-toolkit/prompt-toolkit-3.0.39.ebuild b/dev-python/prompt-toolkit/prompt-toolkit-3.0.39.ebuild
index 26d942bdec3c5..4c44596a1cbe4 100644
--- a/dev-python/prompt-toolkit/prompt-toolkit-3.0.39.ebuild
+++ b/dev-python/prompt-toolkit/prompt-toolkit-3.0.39.ebuild
@@ -16,7 +16,7 @@ HOMEPAGE="
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	dev-python/wcwidth[${PYTHON_USEDEP}]
diff --git a/dev-python/pure_eval/pure_eval-0.2.2.ebuild b/dev-python/pure_eval/pure_eval-0.2.2.ebuild
index 4b88c6675a5c6..f6b8830721975 100644
--- a/dev-python/pure_eval/pure_eval-0.2.2.ebuild
+++ b/dev-python/pure_eval/pure_eval-0.2.2.ebuild
@@ -12,7 +12,7 @@ HOMEPAGE="https://github.com/alexmojaki/pure_eval"
 
 LICENSE="MIT"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 BDEPEND="dev-python/wheel[${PYTHON_USEDEP}]"
 
diff --git a/dev-python/pyzmq/pyzmq-25.1.1.ebuild b/dev-python/pyzmq/pyzmq-25.1.1.ebuild
index ecdc730d9117a..8e9fe7aa8a243 100644
--- a/dev-python/pyzmq/pyzmq-25.1.1.ebuild
+++ b/dev-python/pyzmq/pyzmq-25.1.1.ebuild
@@ -23,7 +23,7 @@ SRC_URI="
 
 LICENSE="LGPL-3"
 SLOT="0"
-KEYWORDS="~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~m68k ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~amd64-linux ~x86-linux"
+KEYWORDS="~amd64 ~arm ~arm64 ~hppa ~ia64 ~loong ~m68k ~mips ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~amd64-linux ~x86-linux ~arm64-macos ~x64-macos"
 IUSE="drafts"
 
 # There are additional test failures if zeromq has the draft api enabled, but pyzmq has it disabled.
diff --git a/dev-python/stack_data/stack_data-0.6.2.ebuild b/dev-python/stack_data/stack_data-0.6.2.ebuild
index 08739e4bc1bf9..7714a2d638383 100644
--- a/dev-python/stack_data/stack_data-0.6.2.ebuild
+++ b/dev-python/stack_data/stack_data-0.6.2.ebuild
@@ -16,7 +16,7 @@ HOMEPAGE="
 
 LICENSE="MIT"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 RDEPEND="
 	>=dev-python/asttokens-2.1.0[${PYTHON_USEDEP}]
diff --git a/dev-python/traitlets/traitlets-5.9.0.ebuild b/dev-python/traitlets/traitlets-5.9.0.ebuild
index b0e0ab3aee782..90d5b0e2bb996 100644
--- a/dev-python/traitlets/traitlets-5.9.0.ebuild
+++ b/dev-python/traitlets/traitlets-5.9.0.ebuild
@@ -16,7 +16,7 @@ HOMEPAGE="
 
 LICENSE="BSD"
 SLOT="0"
-KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ~mips ppc ppc64 ~riscv ~s390 sparc x86"
+KEYWORDS="amd64 arm arm64 hppa ~ia64 ~loong ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~arm64-macos ~x64-macos"
 
 BDEPEND="
 	test? (
diff --git a/dev-python/twisted/twisted-22.10.0-r3.ebuild b/dev-python/twisted/twisted-22.10.0-r3.ebuild
index 6e6c04351cec3..e611173baef2f 100644
--- a/dev-python/twisted/twisted-22.10.0-r3.ebuild
+++ b/dev-python/twisted/twisted-22.10.0-r3.ebuild
@@ -20,7 +20,7 @@ S=${WORKDIR}/${PN}-${P}
 
 LICENSE="MIT"
 SLOT="0"
-KEYWORDS="~alpha ~amd64 ~arm arm64 ~hppa ~ia64 ~loong ~m68k ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86"
+KEYWORDS="~alpha ~amd64 ~arm arm64 ~hppa ~ia64 ~loong ~m68k ~ppc ~ppc64 ~riscv ~s390 ~sparc ~x86 ~arm64-macos ~x64-macos"
 IUSE="conch http2 serial ssl test"
 RESTRICT="!test? ( test )"
 
diff --git a/dev-python/wcwidth/wcwidth-0.2.6.ebuild b/dev-python/wcwidth/wcwidth-0.2.6.ebuild
index 3360f9a63125f..4a576f125eb20 100644
--- a/dev-python/wcwidth/wcwidth-0.2.6.ebuild
+++ b/dev-python/wcwidth/wcwidth-0.2.6.ebuild
@@ -20,7 +20,7 @@ SRC_URI="
 
 SLOT="0"
 LICENSE="MIT"
-KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~amd64-linux ~x86-linux"
+KEYWORDS="~alpha amd64 arm arm64 hppa ~ia64 ~loong ~m68k ~mips ppc ppc64 ~riscv ~s390 sparc x86 ~amd64-linux ~x86-linux ~arm64-macos ~x64-macos"
 
 distutils_enable_tests pytest