diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 5f80dfd0f1ad..0c10b45b609a 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -31,7 +31,6 @@ jobs:
           - {VERSION: "3.12", NOXSESSION: "rust"}
           - {VERSION: "3.12", NOXSESSION: "docs", OPENSSL: {TYPE: "openssl", VERSION: "3.2.2"}}
           - {VERSION: "3.13-dev", NOXSESSION: "tests"}
-          - {VERSION: "pypy-3.9", NOXSESSION: "tests-nocoverage"}
           - {VERSION: "pypy-3.10", NOXSESSION: "tests-nocoverage"}
           - {VERSION: "3.12", NOXSESSION: "tests", OPENSSL: {TYPE: "openssl", VERSION: "3.0.14"}}
           - {VERSION: "3.12", NOXSESSION: "tests", OPENSSL: {TYPE: "openssl", VERSION: "3.1.6"}}
diff --git a/.github/workflows/wheel-builder.yml b/.github/workflows/wheel-builder.yml
index 68930e5978d7..5413c9d3f96b 100644
--- a/.github/workflows/wheel-builder.yml
+++ b/.github/workflows/wheel-builder.yml
@@ -63,7 +63,6 @@ jobs:
         PYTHON:
           - { VERSION: "cp311-cp311", ABI_VERSION: 'py37' }
           - { VERSION: "cp311-cp311", ABI_VERSION: 'py39' }
-          - { VERSION: "pp39-pypy39_pp73" }
           - { VERSION: "pp310-pypy310_pp73" }
         MANYLINUX:
           - { NAME: "manylinux2014_x86_64", CONTAINER: "cryptography-manylinux2014:x86_64", RUNNER: "ubuntu-latest" }
@@ -75,22 +74,14 @@ jobs:
           - { NAME: "musllinux_1_2_aarch64", CONTAINER: "cryptography-musllinux_1_2:aarch64", RUNNER: [self-hosted, Linux, ARM64]}
         exclude:
           # There are no readily available musllinux PyPy distributions
-          - PYTHON: { VERSION: "pp39-pypy39_pp73" }
-            MANYLINUX: { NAME: "musllinux_1_2_x86_64", CONTAINER: "cryptography-musllinux_1_2:x86_64", RUNNER: "ubuntu-latest"}
           - PYTHON: { VERSION: "pp310-pypy310_pp73" }
             MANYLINUX: { NAME: "musllinux_1_2_x86_64", CONTAINER: "cryptography-musllinux_1_2:x86_64", RUNNER: "ubuntu-latest"}
-          - PYTHON: { VERSION: "pp39-pypy39_pp73" }
-            MANYLINUX: { NAME: "musllinux_1_2_aarch64", CONTAINER: "cryptography-musllinux_1_2:aarch64", RUNNER: [self-hosted, Linux, ARM64]}
           - PYTHON: { VERSION: "pp310-pypy310_pp73" }
             MANYLINUX: { NAME: "musllinux_1_2_aarch64", CONTAINER: "cryptography-musllinux_1_2:aarch64", RUNNER: [self-hosted, Linux, ARM64]}
 
             # We also don't build pypy wheels for anything except the latest manylinux
-          - PYTHON: { VERSION: "pp39-pypy39_pp73" }
-            MANYLINUX: { NAME: "manylinux2014_x86_64", CONTAINER: "cryptography-manylinux2014:x86_64", RUNNER: "ubuntu-latest"}
           - PYTHON: { VERSION: "pp310-pypy310_pp73" }
             MANYLINUX: { NAME: "manylinux2014_x86_64", CONTAINER: "cryptography-manylinux2014:x86_64", RUNNER: "ubuntu-latest"}
-          - PYTHON: { VERSION: "pp39-pypy39_pp73" }
-            MANYLINUX: { NAME: "manylinux2014_aarch64", CONTAINER: "cryptography-manylinux2014_aarch64", RUNNER: [self-hosted, Linux, ARM64]}
           - PYTHON: { VERSION: "pp310-pypy310_pp73" }
             MANYLINUX: { NAME: "manylinux2014_aarch64", CONTAINER: "cryptography-manylinux2014_aarch64", RUNNER: [self-hosted, Linux, ARM64]}
     name: "${{ matrix.PYTHON.VERSION }} for ${{ matrix.MANYLINUX.NAME }}"
@@ -190,11 +181,6 @@ jobs:
             # This will change in the future as we change the base Python we
             # build against
             _PYTHON_HOST_PLATFORM: 'macosx-10.9-universal2'
-          - VERSION: 'pypy-3.9'
-            BIN_PATH: 'pypy3'
-            DEPLOYMENT_TARGET: '10.12'
-            _PYTHON_HOST_PLATFORM: 'macosx-10.9-x86_64'
-            ARCHFLAGS: '-arch x86_64'
           - VERSION: 'pypy-3.10'
             BIN_PATH: 'pypy3'
             DEPLOYMENT_TARGET: '10.12'
@@ -290,12 +276,9 @@ jobs:
         PYTHON:
           - {VERSION: "3.11", "ABI_VERSION": "py37"}
           - {VERSION: "3.11", "ABI_VERSION": "py39"}
-          - {VERSION: "pypy-3.9"}
           - {VERSION: "pypy-3.10"}
         exclude:
           # We need to exclude the below configuration because there is no 32-bit pypy3
-          - WINDOWS: {ARCH: 'x86', WINDOWS: 'win32', RUST_TRIPLE: 'i686-pc-windows-msvc'}
-            PYTHON: {VERSION: "pypy-3.9"}
           - WINDOWS: {ARCH: 'x86', WINDOWS: 'win32', RUST_TRIPLE: 'i686-pc-windows-msvc'}
             PYTHON: {VERSION: "pypy-3.10"}
     name: "${{ matrix.PYTHON.VERSION }} ${{ matrix.WINDOWS.WINDOWS }} ${{ matrix.PYTHON.ABI_VERSION }}"