diff --git a/tools/distrib/install_all_python_modules.sh b/tools/distrib/install_all_python_modules.sh
index b389df483776f..b715eb8cc1795 100755
--- a/tools/distrib/install_all_python_modules.sh
+++ b/tools/distrib/install_all_python_modules.sh
@@ -31,7 +31,7 @@ BASEDIR=$(realpath "$BASEDIR")/../..
 PACKAGES="grpcio_channelz  grpcio_csds  grpcio_admin grpcio_health_checking  grpcio_reflection  grpcio_status  grpcio_testing grpcio_csm_observability grpcio_tests"
 
 (cd "$BASEDIR";
-  pip install --upgrade "cython<3.0.0rc1";
+  pip install --upgrade "cython<4.0.0rc1";
   python setup.py install;
   pushd tools/distrib/python/grpcio_tools;
     ../make_grpcio_tools.py
diff --git a/tools/dockerfile/grpc_artifact_python_linux_armv7/install_python_for_wheel_crosscompilation.sh b/tools/dockerfile/grpc_artifact_python_linux_armv7/install_python_for_wheel_crosscompilation.sh
index 08c6439d36a04..f1f1d39509e9c 100755
--- a/tools/dockerfile/grpc_artifact_python_linux_armv7/install_python_for_wheel_crosscompilation.sh
+++ b/tools/dockerfile/grpc_artifact_python_linux_armv7/install_python_for_wheel_crosscompilation.sh
@@ -44,4 +44,4 @@ popd
 rm -rf "Python-${PYTHON_VERSION}"
 
 # install cython and wheel
-"${PYTHON_PREFIX}/bin/python3" -m pip install --upgrade 'cython<3.0.0rc1' wheel
+"${PYTHON_PREFIX}/bin/python3" -m pip install --upgrade 'cython<4.0.0rc1' wheel
diff --git a/tools/dockerfile/grpc_artifact_python_manylinux2014_aarch64/Dockerfile b/tools/dockerfile/grpc_artifact_python_manylinux2014_aarch64/Dockerfile
index 8e1c0751a8a90..329c4dac51561 100644
--- a/tools/dockerfile/grpc_artifact_python_manylinux2014_aarch64/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_python_manylinux2014_aarch64/Dockerfile
@@ -19,13 +19,13 @@ ENV AUDITWHEEL_PLAT manylinux_2_17_$AUDITWHEEL_ARCH
 
 ###################################
 # Install Python build requirements
-RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<3.0.0rc1'
+RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<4.0.0rc1'
 
 #=================
 # Install ccache
diff --git a/tools/dockerfile/grpc_artifact_python_manylinux2014_x64/Dockerfile b/tools/dockerfile/grpc_artifact_python_manylinux2014_x64/Dockerfile
index ae959de2db4e9..7cda60426789a 100644
--- a/tools/dockerfile/grpc_artifact_python_manylinux2014_x64/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_python_manylinux2014_x64/Dockerfile
@@ -24,13 +24,13 @@ RUN yum update -y && yum install -y curl-devel expat-devel gettext-devel openssl
 
 ###################################
 # Install Python build requirements
-RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<3.0.0rc1'
+RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<4.0.0rc1'
 
 #=================
 # Install ccache
diff --git a/tools/dockerfile/grpc_artifact_python_manylinux2014_x86/Dockerfile b/tools/dockerfile/grpc_artifact_python_manylinux2014_x86/Dockerfile
index 7736403f098bf..f305335f52654 100644
--- a/tools/dockerfile/grpc_artifact_python_manylinux2014_x86/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_python_manylinux2014_x86/Dockerfile
@@ -24,13 +24,13 @@ RUN yum update -y && yum install -y curl-devel expat-devel gettext-devel openssl
 
 ###################################
 # Install Python build requirements
-RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<3.0.0rc1'
+RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<4.0.0rc1'
 
 #=================
 # Install ccache
diff --git a/tools/dockerfile/grpc_artifact_python_musllinux_1_1_x64/Dockerfile b/tools/dockerfile/grpc_artifact_python_musllinux_1_1_x64/Dockerfile
index a6eff9bbe715f..c06858b0db08b 100644
--- a/tools/dockerfile/grpc_artifact_python_musllinux_1_1_x64/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_python_musllinux_1_1_x64/Dockerfile
@@ -16,13 +16,13 @@ FROM quay.io/pypa/musllinux_1_1_x86_64:2023-09-17-ae90a16
 
 ###################################
 # Install Python build requirements
-RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<3.0.0rc1'
+RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<4.0.0rc1'
 
 #=================
 # Install ccache
diff --git a/tools/dockerfile/grpc_artifact_python_musllinux_1_1_x86/Dockerfile b/tools/dockerfile/grpc_artifact_python_musllinux_1_1_x86/Dockerfile
index c7ac549e98fcf..d4f96cfdc150b 100644
--- a/tools/dockerfile/grpc_artifact_python_musllinux_1_1_x86/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_python_musllinux_1_1_x86/Dockerfile
@@ -16,13 +16,13 @@ FROM quay.io/pypa/musllinux_1_1_i686:2023-09-17-ae90a16
 
 ###################################
 # Install Python build requirements
-RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<3.0.0rc1'
-RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<3.0.0rc1'
+RUN /opt/python/cp36-cp36m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp37-cp37m/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp38-cp38/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp39-cp39/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp310-cp310/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp311-cp311/bin/pip install --upgrade 'cython<4.0.0rc1'
+RUN /opt/python/cp312-cp312/bin/pip install --upgrade 'cython<4.0.0rc1'
 
 #=================
 # Install ccache
diff --git a/tools/internal_ci/helper_scripts/requirements.macos.txt b/tools/internal_ci/helper_scripts/requirements.macos.txt
index 59a759b0ce231..57c4fb7abf5bb 100644
--- a/tools/internal_ci/helper_scripts/requirements.macos.txt
+++ b/tools/internal_ci/helper_scripts/requirements.macos.txt
@@ -1,4 +1,4 @@
-cython<3.0.0rc1
+cython<4.0.0rc1
 cryptography==3.4.6
 PyJWT==2.0.1
 pyOpenSSL==20.0.1
diff --git a/tools/internal_ci/macos/grpc_distribtests_python.sh b/tools/internal_ci/macos/grpc_distribtests_python.sh
index 8bd18de2e1d01..e0d305db0f52c 100644
--- a/tools/internal_ci/macos/grpc_distribtests_python.sh
+++ b/tools/internal_ci/macos/grpc_distribtests_python.sh
@@ -26,12 +26,12 @@ source tools/internal_ci/helper_scripts/prepare_build_macos_rc
 
 # TODO(jtattermusch): cleanup this prepare build step (needed for python artifact build)
 # install cython for all python versions
-python3.7 -m pip install -U 'cython<3.0.0rc1' setuptools==65.4.1 wheel --user
-python3.8 -m pip install -U 'cython<3.0.0rc1' setuptools==65.4.1 wheel --user
-python3.9 -m pip install -U 'cython<3.0.0rc1' setuptools==65.4.1 wheel --user
-python3.10 -m pip install -U 'cython<3.0.0rc1' setuptools==65.4.1 wheel --user
-python3.11 -m pip install -U 'cython<3.0.0rc1' setuptools==65.4.1 wheel --user
-python3.12 -m pip install -U 'cython<3.0.0rc1' setuptools==65.4.1 wheel --user
+python3.7 -m pip install -U 'cython<4.0.0rc1' setuptools==65.4.1 wheel --user
+python3.8 -m pip install -U 'cython<4.0.0rc1' setuptools==65.4.1 wheel --user
+python3.9 -m pip install -U 'cython<4.0.0rc1' setuptools==65.4.1 wheel --user
+python3.10 -m pip install -U 'cython<4.0.0rc1' setuptools==65.4.1 wheel --user
+python3.11 -m pip install -U 'cython<4.0.0rc1' setuptools==65.4.1 wheel --user
+python3.12 -m pip install -U 'cython<4.0.0rc1' setuptools==65.4.1 wheel --user
 
 # Build all python macos artifacts (this step actually builds all the binary wheels and source archives)
 tools/run_tests/task_runner.py -f artifact macos python ${TASK_RUNNER_EXTRA_FILTERS} -j 2 -x build_artifacts/sponge_log.xml || FAILED="true"
diff --git a/tools/run_tests/artifacts/build_artifact_python.bat b/tools/run_tests/artifacts/build_artifact_python.bat
index f76ac6b31c7c3..af43acf68c630 100644
--- a/tools/run_tests/artifacts/build_artifact_python.bat
+++ b/tools/run_tests/artifacts/build_artifact_python.bat
@@ -22,7 +22,7 @@ set PATH=C:\msys64\mingw%2\bin;C:\tools\msys64\mingw%2\bin;%PATH%
 python -m pip install --upgrade pip six
 @rem Ping to a single version to make sure we're building the same artifacts
 python -m pip install setuptools==69.5.1 wheel==0.43.0
-python -m pip install --upgrade "cython<3.0.0rc1"
+python -m pip install --upgrade "cython<4.0.0rc1"
 python -m pip install -rrequirements.txt --user
 
 @rem set GRPC_PYTHON_OVERRIDE_CYGWIN_DETECTION_FOR_27=1
diff --git a/tools/run_tests/artifacts/build_artifact_python.sh b/tools/run_tests/artifacts/build_artifact_python.sh
index 1598d2edc183c..2a84f1949aec7 100755
--- a/tools/run_tests/artifacts/build_artifact_python.sh
+++ b/tools/run_tests/artifacts/build_artifact_python.sh
@@ -39,7 +39,7 @@ then
   # Any installation step is a potential source of breakages,
   # so we are trying to perform as few download-and-install operations
   # as possible.
-  "${PYTHON}" -m pip install --upgrade 'cython<3.0.0rc1'
+  "${PYTHON}" -m pip install --upgrade 'cython<4.0.0rc1'
 fi
 
 # Allow build_ext to build C/C++ files in parallel
diff --git a/tools/run_tests/helper_scripts/build_python.sh b/tools/run_tests/helper_scripts/build_python.sh
index 347d5a73c3388..9a092f2443e46 100755
--- a/tools/run_tests/helper_scripts/build_python.sh
+++ b/tools/run_tests/helper_scripts/build_python.sh
@@ -158,7 +158,7 @@ pip_install_dir_and_deps() {
 
 pip_install -U gevent
 
-pip_install --upgrade 'cython<3.0.0rc1'
+pip_install --upgrade 'cython<4.0.0rc1'
 pip_install --upgrade six 'protobuf>=4.21.3rc1,!=4.22.0.*'
 
 if [ "$("$VENV_PYTHON" -c "import sys; print(sys.version_info[0])")" == "2" ]