diff --git a/python/py-awscli2/Portfile b/python/py-awscli2/Portfile
index a9a434a55dcb7..0f343c80e06fa 100644
--- a/python/py-awscli2/Portfile
+++ b/python/py-awscli2/Portfile
@@ -6,7 +6,7 @@ PortGroup           select 1.0
 PortGroup           github 1.0
 
 name                py-awscli2
-github.setup        aws aws-cli 2.22.12
+github.setup        aws aws-cli 2.22.16
 revision            0
 
 categories          python devel
@@ -20,9 +20,9 @@ long_description    {*}${description}
 
 homepage            https://aws.amazon.com/cli/
 
-checksums           rmd160  670c9aa994ed90207310dade572a75547a564468 \
-                    sha256  65d72870ae72afa94cb8cb0ae73e4770b6e8312522872c9172307e03a1c94573 \
-                    size    15803467
+checksums           rmd160  cba86f8367ea42b845b5696ec0fc01e53a4f33db \
+                    sha256  b602955e03d4e7a9556cd87dafea52de3781c5665504186f32196841076e4ca4 \
+                    size    15829749
 
 python.versions     39 310 311 312
 python.pep517       yes
diff --git a/python/py-awscli2/files/patch-requirements.diff b/python/py-awscli2/files/patch-requirements.diff
index 43e09f63e4f82..d0457679ff8c4 100644
--- a/python/py-awscli2/files/patch-requirements.diff
+++ b/python/py-awscli2/files/patch-requirements.diff
@@ -1,19 +1,11 @@
 Keep awscrt pinned. This is the only user, and presumably
 Amazon has a good reason for not bumping the version yet.
 
-diff -ru aws-cli-2.11.0-orig/pyproject.toml aws-cli-2.11.0/pyproject.toml
---- aws-cli-2.11.0-orig/pyproject.toml	2023-03-02 19:00:36.000000000 -0500
-+++ aws-cli-2.11.0/pyproject.toml	2023-03-03 11:05:13.214881849 -0500
-@@ -1,6 +1,6 @@
- [build-system]
- requires = [
--"flit_core>=3.7.1,<3.9.1",
-+"flit_core",
- ]
- build-backend = "pep517"
- backend-path = ["backends"]
-@@ -28,21 +28,21 @@
-     "Programming Language :: Python :: 3.11",
+diff -ru aws-cli-2.22.16-orig/pyproject.toml aws-cli-2.22.16/pyproject.toml
+--- aws-cli-2.22.16-orig/pyproject.toml	2024-12-12 20:43:54.480484769 -0500
++++ aws-cli-2.22.16/pyproject.toml	2024-12-12 20:52:57.202110859 -0500
+@@ -30,25 +30,23 @@
+     'Programming Language :: Python :: 3.12',
  ]
  dependencies = [
 -    "colorama>=0.2.5,<0.4.7",
@@ -31,10 +23,14 @@ diff -ru aws-cli-2.11.0-orig/pyproject.toml aws-cli-2.11.0/pyproject.toml
 -    "ruamel.yaml.clib>=0.2.0,<=0.2.8",
 -    "prompt-toolkit>=3.0.24,<3.0.39",
 -    "distro>=1.5.0,<1.9.0",
--    "awscrt>=0.19.18,<=0.22.0",
+-    "awscrt==0.23.4",
 -    "python-dateutil>=2.1,<=2.9.0",
 -    "jmespath>=0.7.1,<1.1.0",
 -    "urllib3>=1.25.4,<1.27",
+-    # zipp>=3.21.0 dropped support for Python 3.8. In order to ensure
+-    # we have a consistent dependency closure across all Python
+-    # versions, we explicitly include zipp as a dependency.
+-    "zipp<3.21.0",
 +    "ruamel.yaml.clib",
 +    "prompt-toolkit",
 +    "distro",
@@ -42,6 +38,8 @@ diff -ru aws-cli-2.11.0-orig/pyproject.toml aws-cli-2.11.0/pyproject.toml
 +    "python-dateutil",
 +    "jmespath",
 +    "urllib3",
++    # MacPorts py-import-lib-metadata has the zipp dependency that
++    # was specified in here.
  ]
  dynamic = ["version"]
 
diff --git a/python/py-awscrt/Portfile b/python/py-awscrt/Portfile
index 939bc0b54eb85..fd4e7ffd0e60a 100644
--- a/python/py-awscrt/Portfile
+++ b/python/py-awscrt/Portfile
@@ -6,11 +6,10 @@ PortGroup           python 1.0
 name                py-awscrt
 # This is only used by awscli2. Bump when Amazon bumps
 # their pinned version in awscli2's setup.cfg.
-version             0.22.0
+version             0.23.4
 revision            0
 
 categories-append   devel
-platforms           darwin
 maintainers         {gmail.com:davidgilman1 @dgilman} openmaintainer
 license             Apache-2
 
@@ -19,11 +18,11 @@ long_description    {*}${description}
 
 homepage            https://aws.amazon.com/cli/
 
-checksums           rmd160  d19cdb0a483367f7e4e51dfae96c62a662e62ab1 \
-                    sha256  4ca2b0b49328f03f5a3dde2d565132df8ad74cba27352612ecd9fe2505e1d770 \
-                    size    64353345
+checksums           rmd160  3db3c29341ea8811313e579b0692ac0bba8f34b5 \
+                    sha256  3ef5212a3c3b0549b3b0e85507b7bbdfb891ff40ca4c597e92db07a0bf7b614a \
+                    size    65405449
 
-python.versions     39 310 311 312
+python.versions     39 310 311 312 313
 
 if {${name} ne ${subport}} {
     if {${os.platform} eq "darwin" && ${os.major} <= 18} {