diff --git a/templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0/Dockerfile.template b/templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0/Dockerfile.template
similarity index 91%
rename from templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0/Dockerfile.template
rename to templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0/Dockerfile.template
index 2bff360192c..b8da129ddb3 100644
--- a/templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0/Dockerfile.template
+++ b/templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0/Dockerfile.template
@@ -14,10 +14,11 @@
   # See the License for the specific language governing permissions and
   # limitations under the License.
 
-  FROM debian:10
+  FROM debian:11
 
   <%include file="../../apt_get_basic.include"/>
   <%include file="../../ruby_3_0_deps.include"/>
+  <%include file="../../rvm_mkdir_workaround.include"/>
 
   # Define the default command.
   CMD ["bash"]
diff --git a/templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1/Dockerfile.template b/templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1/Dockerfile.template
similarity index 91%
rename from templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1/Dockerfile.template
rename to templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1/Dockerfile.template
index a0f67ff7d89..a9e4abe237d 100644
--- a/templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1/Dockerfile.template
+++ b/templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1/Dockerfile.template
@@ -14,10 +14,11 @@
   # See the License for the specific language governing permissions and
   # limitations under the License.
 
-  FROM debian:10
+  FROM debian:11
 
   <%include file="../../apt_get_basic.include"/>
   <%include file="../../ruby_3_1_deps.include"/>
+  <%include file="../../rvm_mkdir_workaround.include"/>
 
   # Define the default command.
   CMD ["bash"]
diff --git a/templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2/Dockerfile.template b/templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2/Dockerfile.template
similarity index 91%
rename from templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2/Dockerfile.template
rename to templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2/Dockerfile.template
index a19720ff436..35575ac4c68 100644
--- a/templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2/Dockerfile.template
+++ b/templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2/Dockerfile.template
@@ -14,10 +14,11 @@
   # See the License for the specific language governing permissions and
   # limitations under the License.
 
-  FROM debian:10
+  FROM debian:11
 
   <%include file="../../apt_get_basic.include"/>
   <%include file="../../ruby_3_2_deps.include"/>
+  <%include file="../../rvm_mkdir_workaround.include"/>
 
   # Define the default command.
   CMD ["bash"]
diff --git a/templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3/Dockerfile.template b/templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3/Dockerfile.template
similarity index 91%
rename from templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3/Dockerfile.template
rename to templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3/Dockerfile.template
index 8fc44ef1a80..dcdcf5a5b6d 100644
--- a/templates/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3/Dockerfile.template
+++ b/templates/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3/Dockerfile.template
@@ -14,10 +14,11 @@
   # See the License for the specific language governing permissions and
   # limitations under the License.
 
-  FROM debian:10
+  FROM debian:11
 
   <%include file="../../apt_get_basic.include"/>
   <%include file="../../ruby_3_3_deps.include"/>
+  <%include file="../../rvm_mkdir_workaround.include"/>
 
   # Define the default command.
   CMD ["bash"]
diff --git a/templates/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile.template b/templates/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile.template
index e53ac1c7ff1..e9689394bb1 100644
--- a/templates/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile.template
+++ b/templates/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile.template
@@ -18,11 +18,11 @@
   
   <%include file="../../apt_get_basic.include"/>
   <%include file="../../run_tests_python_deps.include"/>
-  <%include file="../../ruby_deps.include"/>
+  <%include file="../../ruby_3_0_deps.include"/>
+  <%include file="../../rvm_mkdir_workaround.include"/>
   <%include file="../../cmake.include"/>
   <%include file="../../ccache.include"/>
   <%include file="../../run_tests_addons.include"/>
 
   # Define the default command.
-  CMD ["bash"]
-  
+  CMD ["bash"]
\ No newline at end of file
diff --git a/templates/tools/dockerfile/ruby_deps.include b/templates/tools/dockerfile/ruby_deps.include
deleted file mode 100644
index a57130f9bcc..00000000000
--- a/templates/tools/dockerfile/ruby_deps.include
+++ /dev/null
@@ -1,17 +0,0 @@
-#==================
-# Ruby dependencies
-
-# Install rvm
-RUN apt-get update && apt-get install -y gnupg2 && apt-get clean
-RUN gpg2 --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
-RUN \curl -sSL https://get.rvm.io | bash -s stable
-
-# Install Ruby 2.7
-RUN apt-get update && apt-get install -y procps && apt-get clean
-# "--disable-binary" is a workaround for https://github.com/rvm/rvm/issues/4975
-RUN /bin/bash -l -c "rvm install ruby-2.7 --disable-binary"
-RUN /bin/bash -l -c "rvm use --default ruby-2.7"
-RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
-RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.7' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-document"
diff --git a/templates/tools/dockerfile/rvm_mkdir_workaround.include b/templates/tools/dockerfile/rvm_mkdir_workaround.include
new file mode 100644
index 00000000000..07a4e87a708
--- /dev/null
+++ b/templates/tools/dockerfile/rvm_mkdir_workaround.include
@@ -0,0 +1,3 @@
+# Workaround for rvm unable to find mkdir properly
+# https://stackoverflow.com/questions/64653051
+RUN ln -s /bin/mkdir /usr/bin/mkdir
diff --git a/templates/tools/dockerfile/test/ruby_debian11_arm64/Dockerfile.template b/templates/tools/dockerfile/test/ruby_debian11_arm64/Dockerfile.template
index dd7db3b1133..077ce99d860 100644
--- a/templates/tools/dockerfile/test/ruby_debian11_arm64/Dockerfile.template
+++ b/templates/tools/dockerfile/test/ruby_debian11_arm64/Dockerfile.template
@@ -18,7 +18,8 @@
   
   <%include file="../../apt_get_basic.include"/>
   <%include file="../../run_tests_python_deps.include"/>
-  <%include file="../../ruby_deps.include"/>
+  <%include file="../../ruby_3_0_deps.include"/>
+  <%include file="../../rvm_mkdir_workaround.include"/>
   <%include file="../../cmake.include"/>
   <%include file="../../ccache.include"/>
   <%include file="../../run_tests_addons.include"/>
diff --git a/templates/tools/dockerfile/test/ruby_debian11_x64/Dockerfile.template b/templates/tools/dockerfile/test/ruby_debian11_x64/Dockerfile.template
index 9d24d767888..f8a01a3cdb5 100644
--- a/templates/tools/dockerfile/test/ruby_debian11_x64/Dockerfile.template
+++ b/templates/tools/dockerfile/test/ruby_debian11_x64/Dockerfile.template
@@ -18,7 +18,8 @@
   
   <%include file="../../apt_get_basic.include"/>
   <%include file="../../run_tests_python_deps.include"/>
-  <%include file="../../ruby_deps.include"/>
+  <%include file="../../ruby_3_0_deps.include"/>
+  <%include file="../../rvm_mkdir_workaround.include"/>
   <%include file="../../cmake.include"/>
   <%include file="../../ccache.include"/>
   <%include file="../../run_tests_addons.include"/>
diff --git a/tools/bazelify_tests/dockerimage_current_versions.bzl b/tools/bazelify_tests/dockerimage_current_versions.bzl
index 638fdcaada4..281016b5b8d 100644
--- a/tools/bazelify_tests/dockerimage_current_versions.bzl
+++ b/tools/bazelify_tests/dockerimage_current_versions.bzl
@@ -55,12 +55,10 @@ DOCKERIMAGE_CURRENT_VERSIONS = {
     "tools/dockerfile/distribtest/python_ubuntu2004_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/python_ubuntu2004_x64@sha256:342e9dc23b674ad256b220745745be818708a1baa25a2690f0d4f777e28a22a3",
     "tools/dockerfile/distribtest/python_ubuntu2204_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/python_ubuntu2204_x64@sha256:b6ca497348741615406d1d571cf5042008da934c4f708877aa06a66b5dc3036c",
     "tools/dockerfile/distribtest/ruby_centos7_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_centos7_x64@sha256:4d529b984b78ca179086f7f9b416605e2d9a96ca0a28a71f4421bb5ffdc18f96",
-    "tools/dockerfile/distribtest/ruby_debian10_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64@sha256:1298c39c950b2a48261555b6cff1ae66230a5020f100d3b381759285f0caf84e",
-    "tools/dockerfile/distribtest/ruby_debian10_x64_ruby_2_7.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_2_7@sha256:5ee26ad3abe2683c9a8ee03987ab0ae63f50793c3d3f5e4be6e6cbacb4556fcf",
-    "tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_3_0@sha256:be9dfa852af7fe5c700747bbad5b93d15c3f030ac980a107e98fc9b70fee6077",
-    "tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_3_1@sha256:282a052275fa9e0378301d759f5febcc9f1ff0ebb702e536690cd4fed1a43904",
-    "tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_3_2@sha256:f1ba9030d7d7496a6ed42c0e1a9a2fe3204208e94983d7d4b6b4c7752042ed28",
-    "tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_3_3@sha256:a26d6bfe8f799ae817db0bd0280283c2cc9ea0f02174fe9a2cb0cd10d71d81f8",
+    "tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64_ruby_3_0@sha256:ed855e283001ea9f526aea3830e93c2138194e1740cf6aa5e11a19f6d81e0e22",
+    "tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64_ruby_3_1@sha256:17e3f48a1e1ec2caade5ce4db73f92d6f1f27b34d7cba61968d8b3e3d15f9ca3",
+    "tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64_ruby_3_2@sha256:aa5bf946f601a3ee557be63816428e6a4c997f33194c1a58499d0ca17e7bf562",
+    "tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64_ruby_3_3@sha256:7643e5e91e9f24dc403ad967372c6a6b9a92ccb98fddaa5c29087e5e4ddb1f11",
     "tools/dockerfile/distribtest/ruby_ubuntu2004_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_ubuntu2004_x64@sha256:426cbf625df0c0e7451b9716041996dc6a35a3788c1a24d68891256f84733d8e",
     "tools/dockerfile/distribtest/ruby_ubuntu2204_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_ubuntu2204_x64@sha256:1c74c312f8a4ab37e629732a35daa3056e12136b90f37540cdf9fa11303c7eb8",
     "tools/dockerfile/grpc_artifact_centos6_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/grpc_artifact_centos6_x64@sha256:3285047265ea2b7c5d4df4c769b2d05f56288d947c75e16d27ae2dee693f791b",
@@ -87,7 +85,7 @@ DOCKERIMAGE_CURRENT_VERSIONS = {
     "tools/dockerfile/interoptest/grpc_interop_php7.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/grpc_interop_php7@sha256:9342ff81689c37d9e79fd6abcc08bf310eb48174e83bd3bfce39d225c02f0d4e",
     "tools/dockerfile/interoptest/grpc_interop_python.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/grpc_interop_python@sha256:1f55faacfb4be587e6d26b05561e79bf3e17fe81c69a990e8aeca4257081c9ac",
     "tools/dockerfile/interoptest/grpc_interop_pythonasyncio.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/grpc_interop_pythonasyncio@sha256:47127a7863097b436613885a8866a2ef055470452838ceebb31f692ac88ac1d1",
-    "tools/dockerfile/interoptest/grpc_interop_ruby.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/grpc_interop_ruby@sha256:7b044d6848f82234dba81b38d8eca220b608f830f93b42932df59ed6fe20b24d",
+    "tools/dockerfile/interoptest/grpc_interop_ruby.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/grpc_interop_ruby@sha256:efd7f41a736dd4b8f73b32f5215b86f6bfe9013c422dfcd77978de0253aaee45",
     "tools/dockerfile/interoptest/lb_interop_fake_servers.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/lb_interop_fake_servers@sha256:b89a51dd9147e1293f50ee64dd719fce5929ca7894d3770a3d80dbdecb99fd52",
     "tools/dockerfile/test/android_ndk.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/android_ndk@sha256:2866e815ceaf7407a9017842b86c1bf1efc96abe77ecff88e932aa1b1ddf727e",
     "tools/dockerfile/test/bazel.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/bazel@sha256:32bde2dcb2087f2a32afab59e4dfedf7e8c76a52c69881f63a239d311f0e5ecf",
@@ -112,7 +110,7 @@ DOCKERIMAGE_CURRENT_VERSIONS = {
     "tools/dockerfile/test/python_debian11_default_arm64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/python_debian11_default_arm64@sha256:fccca33a655c7aa89dd7ebd9492cbcc1f636bd2a004cd939d1982cfce3d68326",
     "tools/dockerfile/test/python_debian11_default_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/python_debian11_default_x64@sha256:a956ff4bfbfa4fc6a00c7113f2dada7ce8cf4011f236f07197732981875d6519",
     "tools/dockerfile/test/rbe_ubuntu2004.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/rbe_ubuntu2004@sha256:d3951aeadf43e3bee6adc5b86d26cdaf0b9d1b5baf790d7b2530d1c197adc9f8",
-    "tools/dockerfile/test/ruby_debian11_arm64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_arm64@sha256:7e77cf17e2e8657f4cc23ac9f93630bf13213fff961799e0f16dae17cd45cf6d",
-    "tools/dockerfile/test/ruby_debian11_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64@sha256:e4cb502caccf2db733268ce2ddc951fda8a9df2f7f53d6b74523c33d40c83006",
+    "tools/dockerfile/test/ruby_debian11_arm64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_arm64@sha256:d2e79919b2e2d4cc36a29682ecb5170641df4fb506cfb453978ffdeb8a841bd9",
+    "tools/dockerfile/test/ruby_debian11_x64.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64@sha256:f8fc0ec22065278e5bc02ad7f9a68191e46d083035b3a90ed587561dba9c58c5",
     "tools/dockerfile/test/sanity.current_version": "docker://us-docker.pkg.dev/grpc-testing/testing-images-public/sanity@sha256:ca65b29302e8e381aabf9deb1952281f4e9963654e19c3d681148b5aa972c8a2",
 }
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64.current_version b/tools/dockerfile/distribtest/ruby_debian10_x64.current_version
deleted file mode 100644
index 8bfb13b7315..00000000000
--- a/tools/dockerfile/distribtest/ruby_debian10_x64.current_version
+++ /dev/null
@@ -1 +0,0 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64:0efa3a484833ce2b8960ad449d62571a8d595f65@sha256:1298c39c950b2a48261555b6cff1ae66230a5020f100d3b381759285f0caf84e
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64/Dockerfile b/tools/dockerfile/distribtest/ruby_debian10_x64/Dockerfile
deleted file mode 100644
index bc78b44b1b1..00000000000
--- a/tools/dockerfile/distribtest/ruby_debian10_x64/Dockerfile
+++ /dev/null
@@ -1,19 +0,0 @@
-# Copyright 2015 gRPC authors.
-#
-# Licensed under the Apache License, Version 2.0 (the "License");
-# you may not use this file except in compliance with the License.
-# You may obtain a copy of the License at
-#
-#     http://www.apache.org/licenses/LICENSE-2.0
-#
-# Unless required by applicable law or agreed to in writing, software
-# distributed under the License is distributed on an "AS IS" BASIS,
-# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
-# See the License for the specific language governing permissions and
-# limitations under the License.
-
-FROM debian:10
-
-RUN apt-get update && apt-get install -y ruby-full
-
-RUN gem install bundler -v 1.17.3 --no-document
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_2_7.current_version b/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_2_7.current_version
deleted file mode 100644
index a9be0430e59..00000000000
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_2_7.current_version
+++ /dev/null
@@ -1 +0,0 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_2_7:9a09a0a915e62249957791eda907a011078c5aea@sha256:5ee26ad3abe2683c9a8ee03987ab0ae63f50793c3d3f5e4be6e6cbacb4556fcf
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_2_7/Dockerfile b/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_2_7/Dockerfile
deleted file mode 100644
index 678822a73f4..00000000000
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_2_7/Dockerfile
+++ /dev/null
@@ -1,42 +0,0 @@
-# Copyright 2020 gRPC authors.
-#
-# Licensed under the Apache License, Version 2.0 (the "License");
-# you may not use this file except in compliance with the License.
-# You may obtain a copy of the License at
-#
-#     http://www.apache.org/licenses/LICENSE-2.0
-#
-# Unless required by applicable law or agreed to in writing, software
-# distributed under the License is distributed on an "AS IS" BASIS,
-# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
-# See the License for the specific language governing permissions and
-# limitations under the License.
-
-FROM debian:10
-
-# Install Git and basic packages.
-RUN apt-get update && apt-get install -y \
-  gnupg2 \
-  procps \
-  curl \
-  gcc && apt-get clean
-
-#==================
-# Ruby dependencies
-
-# Install rvm
-RUN gpg2 --keyserver hkp://keyserver.ubuntu.com --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
-RUN \curl -sSL https://get.rvm.io | bash -s stable
-
-# Install Ruby 2.7
-RUN /bin/bash -l -c "rvm install ruby-2.7.0"
-RUN /bin/bash -l -c "rvm use --default ruby-2.7.0"
-RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
-RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.7.0' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-document"
-
-RUN mkdir /var/local/jenkins
-
-# Define the default command.
-CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0.current_version b/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0.current_version
deleted file mode 100644
index 709c65daebb..00000000000
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0.current_version
+++ /dev/null
@@ -1 +0,0 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_3_0:dce91a018316b35b962e5fa576fded4775457077@sha256:be9dfa852af7fe5c700747bbad5b93d15c3f030ac980a107e98fc9b70fee6077
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1.current_version b/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1.current_version
deleted file mode 100644
index 4995cf042c1..00000000000
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1.current_version
+++ /dev/null
@@ -1 +0,0 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_3_1:348a4b975f4d19772bb9a1a95fc03720f89edbc0@sha256:282a052275fa9e0378301d759f5febcc9f1ff0ebb702e536690cd4fed1a43904
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2.current_version b/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2.current_version
deleted file mode 100644
index f17c0cea7c5..00000000000
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2.current_version
+++ /dev/null
@@ -1 +0,0 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_3_2:e9f8640c6bb80a029c65ed6ebdfddd9574a041e4@sha256:f1ba9030d7d7496a6ed42c0e1a9a2fe3204208e94983d7d4b6b4c7752042ed28
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3.current_version b/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3.current_version
deleted file mode 100644
index bbe14a70714..00000000000
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3.current_version
+++ /dev/null
@@ -1 +0,0 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian10_x64_ruby_3_3:c063f13c0987355593ce6bcf2123bb9717eeba35@sha256:a26d6bfe8f799ae817db0bd0280283c2cc9ea0f02174fe9a2cb0cd10d71d81f8
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0.current_version b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0.current_version
new file mode 100644
index 00000000000..4af2537fbb4
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0.current_version
@@ -0,0 +1 @@
+us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64_ruby_3_0:ddf5f067d1e4ae46f4178ef14d2ea2cea6ae6c76@sha256:ed855e283001ea9f526aea3830e93c2138194e1740cf6aa5e11a19f6d81e0e22
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0/Dockerfile b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0/Dockerfile
similarity index 93%
rename from tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0/Dockerfile
rename to tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0/Dockerfile
index 639bd90158c..0bebd8eabb7 100644
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_0/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_0/Dockerfile
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-FROM debian:10
+FROM debian:11
 
 #=================
 # Basic C core dependencies
@@ -79,6 +79,10 @@ RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
 RUN /bin/bash -l -c "echo 'rvm --default use ruby-3.0.5' >> ~/.bashrc"
 RUN /bin/bash -l -c "gem install bundler --no-document"
 
+# Workaround for rvm unable to find mkdir properly
+# https://stackoverflow.com/questions/64653051
+RUN ln -s /bin/mkdir /usr/bin/mkdir
+
 
 # Define the default command.
 CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1.current_version b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1.current_version
new file mode 100644
index 00000000000..f4d4d464ffd
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1.current_version
@@ -0,0 +1 @@
+us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64_ruby_3_1:d6f1ff5cee79b1c3829573d15ea68c5b453f2f8d@sha256:17e3f48a1e1ec2caade5ce4db73f92d6f1f27b34d7cba61968d8b3e3d15f9ca3
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1/Dockerfile b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1/Dockerfile
similarity index 93%
rename from tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1/Dockerfile
rename to tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1/Dockerfile
index 314b0d889fb..2bd1f138737 100644
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_1/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_1/Dockerfile
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-FROM debian:10
+FROM debian:11
 
 #=================
 # Basic C core dependencies
@@ -79,6 +79,10 @@ RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
 RUN /bin/bash -l -c "echo 'rvm --default use ruby-3.1.3' >> ~/.bashrc"
 RUN /bin/bash -l -c "gem install bundler --no-document"
 
+# Workaround for rvm unable to find mkdir properly
+# https://stackoverflow.com/questions/64653051
+RUN ln -s /bin/mkdir /usr/bin/mkdir
+
 
 # Define the default command.
 CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2.current_version b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2.current_version
new file mode 100644
index 00000000000..2e3cefbb0aa
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2.current_version
@@ -0,0 +1 @@
+us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64_ruby_3_2:88a99c45a0bc5fedd959731d78817781b0b545bc@sha256:aa5bf946f601a3ee557be63816428e6a4c997f33194c1a58499d0ca17e7bf562
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2/Dockerfile b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2/Dockerfile
similarity index 93%
rename from tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2/Dockerfile
rename to tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2/Dockerfile
index 546acc6d0d3..c0f6f1a6e73 100644
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_2/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_2/Dockerfile
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-FROM debian:10
+FROM debian:11
 
 #=================
 # Basic C core dependencies
@@ -79,6 +79,10 @@ RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
 RUN /bin/bash -l -c "echo 'rvm --default use ruby-3.2.0' >> ~/.bashrc"
 RUN /bin/bash -l -c "gem install bundler --no-document"
 
+# Workaround for rvm unable to find mkdir properly
+# https://stackoverflow.com/questions/64653051
+RUN ln -s /bin/mkdir /usr/bin/mkdir
+
 
 # Define the default command.
 CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3.current_version b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3.current_version
new file mode 100644
index 00000000000..387848baa6e
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3.current_version
@@ -0,0 +1 @@
+us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64_ruby_3_3:3fc462641e0ecd88ddd38a3ab14fa70c291f98b0@sha256:7643e5e91e9f24dc403ad967372c6a6b9a92ccb98fddaa5c29087e5e4ddb1f11
\ No newline at end of file
diff --git a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3/Dockerfile b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3/Dockerfile
similarity index 93%
rename from tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3/Dockerfile
rename to tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3/Dockerfile
index f7f27b649f7..dba3a43c844 100644
--- a/tools/dockerfile/distribtest/ruby_debian10_x64_ruby_3_3/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_debian11_x64_ruby_3_3/Dockerfile
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-FROM debian:10
+FROM debian:11
 
 #=================
 # Basic C core dependencies
@@ -79,6 +79,10 @@ RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
 RUN /bin/bash -l -c "echo 'rvm --default use ruby-3.3.0' >> ~/.bashrc"
 RUN /bin/bash -l -c "gem install bundler --no-document"
 
+# Workaround for rvm unable to find mkdir properly
+# https://stackoverflow.com/questions/64653051
+RUN ln -s /bin/mkdir /usr/bin/mkdir
+
 
 # Define the default command.
 CMD ["bash"]
diff --git a/tools/dockerfile/interoptest/grpc_interop_ruby.current_version b/tools/dockerfile/interoptest/grpc_interop_ruby.current_version
index e682c81bed0..a9a2b901f64 100644
--- a/tools/dockerfile/interoptest/grpc_interop_ruby.current_version
+++ b/tools/dockerfile/interoptest/grpc_interop_ruby.current_version
@@ -1 +1 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/grpc_interop_ruby:b234d5eeaa79e9dff66484a1a76d142786064a9c@sha256:7b044d6848f82234dba81b38d8eca220b608f830f93b42932df59ed6fe20b24d
\ No newline at end of file
+us-docker.pkg.dev/grpc-testing/testing-images-public/grpc_interop_ruby:28d14e44cd85d7dbe814c72156be140ab120beec@sha256:efd7f41a736dd4b8f73b32f5215b86f6bfe9013c422dfcd77978de0253aaee45
\ No newline at end of file
diff --git a/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
index 484aa78050c..6aab5501ed4 100644
--- a/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
@@ -95,16 +95,19 @@ RUN apt-get update && apt-get install -y gnupg2 && apt-get clean
 RUN gpg2 --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
 RUN \curl -sSL https://get.rvm.io | bash -s stable
 
-# Install Ruby 2.7
+# Install Ruby 3.0
 RUN apt-get update && apt-get install -y procps && apt-get clean
-# "--disable-binary" is a workaround for https://github.com/rvm/rvm/issues/4975
-RUN /bin/bash -l -c "rvm install ruby-2.7 --disable-binary"
-RUN /bin/bash -l -c "rvm use --default ruby-2.7"
+RUN /bin/bash -l -c "rvm install ruby-3.0.5"
+RUN /bin/bash -l -c "rvm use --default ruby-3.0.5"
 RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
 RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.7' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-3.0.5' >> ~/.bashrc"
 RUN /bin/bash -l -c "gem install bundler --no-document"
 
+# Workaround for rvm unable to find mkdir properly
+# https://stackoverflow.com/questions/64653051
+RUN ln -s /bin/mkdir /usr/bin/mkdir
+
 #=================
 # Install cmake
 # Note that this step should be only used for distributions that have new enough cmake to satisfy gRPC's cmake version requirement.
@@ -130,4 +133,4 @@ RUN mkdir /var/local/jenkins
 
 
 # Define the default command.
-CMD ["bash"]
+CMD ["bash"]
\ No newline at end of file
diff --git a/tools/dockerfile/test/ruby_debian11_arm64.current_version b/tools/dockerfile/test/ruby_debian11_arm64.current_version
index f435625c598..d114eb7fd32 100644
--- a/tools/dockerfile/test/ruby_debian11_arm64.current_version
+++ b/tools/dockerfile/test/ruby_debian11_arm64.current_version
@@ -1 +1 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_arm64:8db47f0dd21c60760dbc6aede225a29e8b5eb469@sha256:7e77cf17e2e8657f4cc23ac9f93630bf13213fff961799e0f16dae17cd45cf6d
\ No newline at end of file
+us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_arm64:710eb956a7f5b98b0e2265dd156d946926a142d9@sha256:d2e79919b2e2d4cc36a29682ecb5170641df4fb506cfb453978ffdeb8a841bd9
\ No newline at end of file
diff --git a/tools/dockerfile/test/ruby_debian11_arm64/Dockerfile b/tools/dockerfile/test/ruby_debian11_arm64/Dockerfile
index 1d0e2b418e3..08e09b5d09a 100644
--- a/tools/dockerfile/test/ruby_debian11_arm64/Dockerfile
+++ b/tools/dockerfile/test/ruby_debian11_arm64/Dockerfile
@@ -95,16 +95,19 @@ RUN apt-get update && apt-get install -y gnupg2 && apt-get clean
 RUN gpg2 --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
 RUN \curl -sSL https://get.rvm.io | bash -s stable
 
-# Install Ruby 2.7
+# Install Ruby 3.0
 RUN apt-get update && apt-get install -y procps && apt-get clean
-# "--disable-binary" is a workaround for https://github.com/rvm/rvm/issues/4975
-RUN /bin/bash -l -c "rvm install ruby-2.7 --disable-binary"
-RUN /bin/bash -l -c "rvm use --default ruby-2.7"
+RUN /bin/bash -l -c "rvm install ruby-3.0.5"
+RUN /bin/bash -l -c "rvm use --default ruby-3.0.5"
 RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
 RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.7' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-3.0.5' >> ~/.bashrc"
 RUN /bin/bash -l -c "gem install bundler --no-document"
 
+# Workaround for rvm unable to find mkdir properly
+# https://stackoverflow.com/questions/64653051
+RUN ln -s /bin/mkdir /usr/bin/mkdir
+
 #=================
 # Install cmake
 # Note that this step should be only used for distributions that have new enough cmake to satisfy gRPC's cmake version requirement.
diff --git a/tools/dockerfile/test/ruby_debian11_x64.current_version b/tools/dockerfile/test/ruby_debian11_x64.current_version
index efcd2708432..cbed14c1281 100644
--- a/tools/dockerfile/test/ruby_debian11_x64.current_version
+++ b/tools/dockerfile/test/ruby_debian11_x64.current_version
@@ -1 +1 @@
-us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64:db4549f16eb39f5e16241e9b434f2cf0df018fc5@sha256:e4cb502caccf2db733268ce2ddc951fda8a9df2f7f53d6b74523c33d40c83006
\ No newline at end of file
+us-docker.pkg.dev/grpc-testing/testing-images-public/ruby_debian11_x64:6dfb957e5de39c71c1ca45338a975f7f98bd59d7@sha256:f8fc0ec22065278e5bc02ad7f9a68191e46d083035b3a90ed587561dba9c58c5
\ No newline at end of file
diff --git a/tools/dockerfile/test/ruby_debian11_x64/Dockerfile b/tools/dockerfile/test/ruby_debian11_x64/Dockerfile
index 796d53a7b46..c9c43f73bd9 100644
--- a/tools/dockerfile/test/ruby_debian11_x64/Dockerfile
+++ b/tools/dockerfile/test/ruby_debian11_x64/Dockerfile
@@ -95,16 +95,19 @@ RUN apt-get update && apt-get install -y gnupg2 && apt-get clean
 RUN gpg2 --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
 RUN \curl -sSL https://get.rvm.io | bash -s stable
 
-# Install Ruby 2.7
+# Install Ruby 3.0
 RUN apt-get update && apt-get install -y procps && apt-get clean
-# "--disable-binary" is a workaround for https://github.com/rvm/rvm/issues/4975
-RUN /bin/bash -l -c "rvm install ruby-2.7 --disable-binary"
-RUN /bin/bash -l -c "rvm use --default ruby-2.7"
+RUN /bin/bash -l -c "rvm install ruby-3.0.5"
+RUN /bin/bash -l -c "rvm use --default ruby-3.0.5"
 RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
 RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.7' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-3.0.5' >> ~/.bashrc"
 RUN /bin/bash -l -c "gem install bundler --no-document"
 
+# Workaround for rvm unable to find mkdir properly
+# https://stackoverflow.com/questions/64653051
+RUN ln -s /bin/mkdir /usr/bin/mkdir
+
 #=================
 # Install cmake
 # Note that this step should be only used for distributions that have new enough cmake to satisfy gRPC's cmake version requirement.
diff --git a/tools/run_tests/artifacts/distribtest_targets.py b/tools/run_tests/artifacts/distribtest_targets.py
index fe71900756f..c367171c331 100644
--- a/tools/run_tests/artifacts/distribtest_targets.py
+++ b/tools/run_tests/artifacts/distribtest_targets.py
@@ -468,22 +468,22 @@ def targets():
         RubyDistribTest(
             "linux",
             "x64",
-            "debian10",
-            ruby_version="ruby_2_7",
+            "debian11",
+            ruby_version="ruby_3_2",
             source=True,
             presubmit=True,
         ),
         RubyDistribTest(
-            "linux", "x64", "debian10", ruby_version="ruby_3_0", presubmit=True
+            "linux", "x64", "debian11", ruby_version="ruby_3_0", presubmit=True
         ),
         RubyDistribTest(
-            "linux", "x64", "debian10", ruby_version="ruby_3_1", presubmit=True
+            "linux", "x64", "debian11", ruby_version="ruby_3_1", presubmit=True
         ),
         RubyDistribTest(
-            "linux", "x64", "debian10", ruby_version="ruby_3_2", presubmit=True
+            "linux", "x64", "debian11", ruby_version="ruby_3_2", presubmit=True
         ),
         RubyDistribTest(
-            "linux", "x64", "debian10", ruby_version="ruby_3_3", presubmit=True
+            "linux", "x64", "debian11", ruby_version="ruby_3_3", presubmit=True
         ),
         RubyDistribTest("linux", "x64", "centos7"),
         RubyDistribTest("linux", "x64", "ubuntu2004"),