diff --git a/Dockerfile b/Dockerfile
index 7eb719e4..48562e59 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -18,8 +18,8 @@ RUN apt-get update -qqy && apt-get -qqy upgrade && apt-get install -qqy \
         make \
         gnupg && \
     export CLOUD_SDK_REPO="cloud-sdk-$(lsb_release -c -s)" && \
-    echo "deb [signed-by=/usr/share/keyrings/cloud.google.gpg] https://packages.cloud.google.com/apt $CLOUD_SDK_REPO main" > /etc/apt/sources.list.d/google-cloud-sdk.list && \
-    curl https://packages.cloud.google.com/apt/doc/apt-key.gpg | tee /usr/share/keyrings/cloud.google.gpg && \
+    echo "deb https://packages.cloud.google.com/apt $CLOUD_SDK_REPO main" > /etc/apt/sources.list.d/google-cloud-sdk.list && \
+    curl https://packages.cloud.google.com/apt/doc/apt-key.gpg | apt-key add - && \
     apt-get update && \
     apt-get install -y google-cloud-cli=${CLOUD_SDK_VERSION}-0 \
         google-cloud-cli-app-engine-python=${CLOUD_SDK_VERSION}-0 \
diff --git a/debian_slim/Dockerfile b/debian_slim/Dockerfile
index 605f511f..891d2ce9 100644
--- a/debian_slim/Dockerfile
+++ b/debian_slim/Dockerfile
@@ -21,8 +21,8 @@ RUN apt-get update -qqy && apt-get -qqy upgrade && apt-get install -qqy \
         git \
         gnupg && \
     export CLOUD_SDK_REPO="cloud-sdk-$(lsb_release -c -s)" && \
-    echo "deb [signed-by=/usr/share/keyrings/cloud.google.gpg] https://packages.cloud.google.com/apt $CLOUD_SDK_REPO main" > /etc/apt/sources.list.d/google-cloud-sdk.list && \
-    curl https://packages.cloud.google.com/apt/doc/apt-key.gpg | tee /usr/share/keyrings/cloud.google.gpg && \
+    echo "deb https://packages.cloud.google.com/apt $CLOUD_SDK_REPO main" > /etc/apt/sources.list.d/google-cloud-sdk.list && \
+    curl https://packages.cloud.google.com/apt/doc/apt-key.gpg | apt-key add - && \
     apt-get update && apt-get install -y google-cloud-cli=${CLOUD_SDK_VERSION}-0 $INSTALL_COMPONENTS && \
     gcloud config set core/disable_usage_reporting true && \
     gcloud config set component_manager/disable_update_check true && \