diff --git a/templates/tools/dockerfile/cmake_jessie_backports.include b/templates/tools/dockerfile/cmake_jessie_backports.include
index 6acb991cd78..1da6ed79190 100644
--- a/templates/tools/dockerfile/cmake_jessie_backports.include
+++ b/templates/tools/dockerfile/cmake_jessie_backports.include
@@ -2,5 +2,5 @@
 # Use cmake 3.6 from jessie-backports
 # should only be used for images based on debian jessie.
 
-RUN echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-RUN apt-get update && apt-get install -t jessie-backports -y cmake && apt-get clean
+RUN echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+RUN apt-get -o Acquire::Check-Valid-Until=false update && apt-get install -t jessie-backports -y cmake && apt-get clean
diff --git a/test/distrib/cpp/run_distrib_test_cmake.sh b/test/distrib/cpp/run_distrib_test_cmake.sh
index 06406a40d29..f0e1b8c8e39 100755
--- a/test/distrib/cpp/run_distrib_test_cmake.sh
+++ b/test/distrib/cpp/run_distrib_test_cmake.sh
@@ -17,8 +17,8 @@ set -ex
 
 cd "$(dirname "$0")/../../.."
 
-echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-apt-get update
+echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+apt-get -o Acquire::Check-Valid-Until=false update
 apt-get install -t jessie-backports -y libssl-dev
 
 # Install c-ares
diff --git a/test/distrib/cpp/run_distrib_test_cmake_as_externalproject.sh b/test/distrib/cpp/run_distrib_test_cmake_as_externalproject.sh
index 59d7674db6d..ea37bd53b4f 100755
--- a/test/distrib/cpp/run_distrib_test_cmake_as_externalproject.sh
+++ b/test/distrib/cpp/run_distrib_test_cmake_as_externalproject.sh
@@ -17,8 +17,8 @@ set -ex
 
 cd "$(dirname "$0")/../../.."
 
-echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-apt-get update
+echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+apt-get -o Acquire::Check-Valid-Until=false update
 apt-get install -t jessie-backports -y libssl-dev
 
 # To increase the confidence that gRPC installation works without depending on
diff --git a/tools/dockerfile/distribtest/cpp_jessie_x64/Dockerfile b/tools/dockerfile/distribtest/cpp_jessie_x64/Dockerfile
index dcab64aaeae..d157a278b1e 100644
--- a/tools/dockerfile/distribtest/cpp_jessie_x64/Dockerfile
+++ b/tools/dockerfile/distribtest/cpp_jessie_x64/Dockerfile
@@ -29,7 +29,7 @@ RUN apt-get update && apt-get install -y \
 
 RUN apt-get update && apt-get install -y golang && apt-get clean
 
-RUN echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-RUN apt-get update && apt-get install -t jessie-backports -y cmake && apt-get clean
+RUN echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+RUN apt-get -o Acquire::Check-Valid-Until=false update && apt-get install -t jessie-backports -y cmake && apt-get clean
 
 CMD ["bash"]
diff --git a/tools/dockerfile/grpc_artifact_linux_x64/Dockerfile b/tools/dockerfile/grpc_artifact_linux_x64/Dockerfile
index 5b2b3dbf6de..07564dc40a9 100644
--- a/tools/dockerfile/grpc_artifact_linux_x64/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_linux_x64/Dockerfile
@@ -72,8 +72,8 @@ RUN apt-get update && apt-get install -y \
 # C# dependencies (needed to build grpc_csharp_ext)
 
 # Use cmake 3.6 from jessie-backports
-RUN echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-RUN apt-get update && apt-get install -t jessie-backports -y cmake && apt-get clean
+RUN echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+RUN apt-get -o Acquire::Check-Valid-Until=false update && apt-get install -t jessie-backports -y cmake && apt-get clean
 
 RUN mkdir /var/local/jenkins
 
diff --git a/tools/dockerfile/grpc_artifact_linux_x86/Dockerfile b/tools/dockerfile/grpc_artifact_linux_x86/Dockerfile
index ee0a7105389..55091f4fffa 100644
--- a/tools/dockerfile/grpc_artifact_linux_x86/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_linux_x86/Dockerfile
@@ -64,8 +64,8 @@ RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-ri --no-rdoc"
 # C# dependencies (needed to build grpc_csharp_ext)
 
 # Use cmake 3.6 from jessie-backports
-RUN echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-RUN apt-get update && apt-get install -t jessie-backports -y cmake && apt-get clean
+RUN echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+RUN apt-get -o Acquire::Check-Valid-Until=false update && apt-get install -t jessie-backports -y cmake && apt-get clean
 
 RUN mkdir /var/local/jenkins
 
diff --git a/tools/dockerfile/test/cxx_jessie_x64/Dockerfile b/tools/dockerfile/test/cxx_jessie_x64/Dockerfile
index c801edfa386..6afad4869fd 100644
--- a/tools/dockerfile/test/cxx_jessie_x64/Dockerfile
+++ b/tools/dockerfile/test/cxx_jessie_x64/Dockerfile
@@ -76,8 +76,8 @@ RUN apt-get update && apt-get -y install libgflags-dev libgtest-dev libc++-dev c
 # Use cmake 3.6 from jessie-backports
 # should only be used for images based on debian jessie.
 
-RUN echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-RUN apt-get update && apt-get install -t jessie-backports -y cmake && apt-get clean
+RUN echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+RUN apt-get -o Acquire::Check-Valid-Until=false update && apt-get install -t jessie-backports -y cmake && apt-get clean
 
 
 RUN mkdir /var/local/jenkins
diff --git a/tools/dockerfile/test/cxx_jessie_x86/Dockerfile b/tools/dockerfile/test/cxx_jessie_x86/Dockerfile
index 3fdbb27f6e1..c153cd037e6 100644
--- a/tools/dockerfile/test/cxx_jessie_x86/Dockerfile
+++ b/tools/dockerfile/test/cxx_jessie_x86/Dockerfile
@@ -79,8 +79,8 @@ RUN mkdir /var/local/jenkins
 # Use cmake 3.6 from jessie-backports
 # should only be used for images based on debian jessie.
 
-RUN echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-RUN apt-get update && apt-get install -t jessie-backports -y cmake && apt-get clean
+RUN echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+RUN apt-get -o Acquire::Check-Valid-Until=false update && apt-get install -t jessie-backports -y cmake && apt-get clean
 
 
 # Install gcc-4.8 and other relevant items
diff --git a/tools/dockerfile/test/fuzzer/Dockerfile b/tools/dockerfile/test/fuzzer/Dockerfile
index ef9305bcc8d..591ca0ce014 100644
--- a/tools/dockerfile/test/fuzzer/Dockerfile
+++ b/tools/dockerfile/test/fuzzer/Dockerfile
@@ -76,8 +76,8 @@ RUN apt-get update && apt-get -y install libgflags-dev libgtest-dev libc++-dev c
 # Use cmake 3.6 from jessie-backports
 # should only be used for images based on debian jessie.
 
-RUN echo "deb [check-valid-until=no] http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
-RUN apt-get update && apt-get install -t jessie-backports -y cmake && apt-get clean
+RUN echo "deb http://archive.debian.org/debian jessie-backports main" | tee /etc/apt/sources.list.d/jessie-backports.list
+RUN apt-get -o Acquire::Check-Valid-Until=false update && apt-get install -t jessie-backports -y cmake && apt-get clean
 
 #=================
 # Update clang to a version with improved tsan and fuzzing capabilities