diff --git a/.github/workflows/build-and-release-runners.yml b/.github/workflows/build-and-release-runners.yml
index c00fed4e..ff71753e 100644
--- a/.github/workflows/build-and-release-runners.yml
+++ b/.github/workflows/build-and-release-runners.yml
@@ -19,8 +19,8 @@ on:
       - .github/workflows/build-and-release-runners.yml
 
 env:
-  RUNNER_VERSION: 2.279.0
-  DOCKER_VERSION: 19.03.12
+  RUNNER_VERSION: 2.280.2
+  DOCKER_VERSION: 20.10.8
   DOCKERHUB_USERNAME: summerwind
 
 jobs:
diff --git a/runner/Dockerfile b/runner/Dockerfile
index 66887c64..ed7b71fa 100644
--- a/runner/Dockerfile
+++ b/runner/Dockerfile
@@ -1,9 +1,9 @@
 FROM ubuntu:20.04
 
 ARG TARGETPLATFORM
-ARG RUNNER_VERSION=2.279.0
+ARG RUNNER_VERSION=2.280.2
 ARG DOCKER_CHANNEL=stable
-ARG DOCKER_VERSION=19.03.12
+ARG DOCKER_VERSION=20.10.8
 ARG DUMB_INIT_VERSION=1.2.5
 
 RUN test -n "$TARGETPLATFORM" || (echo "TARGETPLATFORM must be set" && false)
@@ -56,7 +56,7 @@ RUN set -vx; \
     export ARCH=$(echo ${TARGETPLATFORM} | cut -d / -f2) \
     && if [ "$ARCH" = "arm64" ]; then export ARCH=aarch64 ; fi \
     && if [ "$ARCH" = "amd64" ] || [ "$ARCH" = "i386" ]; then export ARCH=x86_64 ; fi \
-    && curl -L -o docker.tgz https://download.docker.com/linux/static/${DOCKER_CHANNEL}/${ARCH}/docker-${DOCKER_VERSION}.tgz \
+    && curl -f -L -o docker.tgz https://download.docker.com/linux/static/${DOCKER_CHANNEL}/${ARCH}/docker-${DOCKER_VERSION}.tgz \
     && tar zxvf docker.tgz \
     && install -o root -g root -m 755 docker/docker /usr/local/bin/docker \
     && rm -rf docker docker.tgz \
@@ -76,8 +76,8 @@ ENV HOME=/home/runner
 # - Run `cd $repo/src`
 # - Run `./dev.sh layout Release linux-x64`
 # - Run `./dev.sh package Release linux-x64`
-# - Run cp ../_package/actions-runner-linux-x64-2.279.0.tar.gz ../../actions-runner-controller/runner/
-#   - Beware that `2.279.0` might change across versions
+# - Run cp ../_package/actions-runner-linux-x64-2.280.2.tar.gz ../../actions-runner-controller/runner/
+#   - Beware that `2.280.2` might change across versions
 #
 # See https://github.com/actions/runner/blob/main/.github/workflows/release.yml for more informatino on how you can use dev.sh
 #
@@ -85,7 +85,7 @@ ENV HOME=/home/runner
 #   && curl -L -o runner.tar.gz https://github.com/actions/runner/releases/download/v${RUNNER_VERSION}/actions-runner-linux-${ARCH}-${RUNNER_VERSION}.tar.gz \
 # line in the next `RUN` command in this Dockerfile, to avoid overwiding this runner.tar.gz with a remote one.
 
-# COPY actions-runner-linux-x64-2.279.0.tar.gz /runnertmp/runner.tar.gz
+# COPY actions-runner-linux-x64-2.280.2.tar.gz /runnertmp/runner.tar.gz
 
 # Runner download supports amd64 as x64. Externalstmp is needed for making mount points work inside DinD.
 #
@@ -97,7 +97,7 @@ RUN export ARCH=$(echo ${TARGETPLATFORM} | cut -d / -f2) \
     && mkdir -p "$RUNNER_ASSETS_DIR" \
     && cd "$RUNNER_ASSETS_DIR" \
     # Comment-out the below curl invocation when you use your own build of actions/runner
-    && curl -L -o runner.tar.gz https://github.com/actions/runner/releases/download/v${RUNNER_VERSION}/actions-runner-linux-${ARCH}-${RUNNER_VERSION}.tar.gz \
+    && curl -f -L -o runner.tar.gz https://github.com/actions/runner/releases/download/v${RUNNER_VERSION}/actions-runner-linux-${ARCH}-${RUNNER_VERSION}.tar.gz \
     && tar xzf ./runner.tar.gz \
     && rm runner.tar.gz \
     && ./bin/installdependencies.sh \
@@ -115,7 +115,9 @@ COPY --chown=runner:docker patched $RUNNER_ASSETS_DIR/patched
 
 # Add the Python "User Script Directory" to the PATH
 ENV PATH="${PATH}:${HOME}/.local/bin"
+ENV ImageOS=ubuntu20
 
 USER runner
+
 ENTRYPOINT ["/usr/local/bin/dumb-init", "--"]
 CMD ["/entrypoint.sh"]
diff --git a/runner/Dockerfile.dindrunner b/runner/Dockerfile.dindrunner
index 6284cb11..5dff2530 100644
--- a/runner/Dockerfile.dindrunner
+++ b/runner/Dockerfile.dindrunner
@@ -1,7 +1,7 @@
 FROM ubuntu:20.04
 
 ARG TARGETPLATFORM
-ARG RUNNER_VERSION=2.279.0
+ARG RUNNER_VERSION=2.280.2
 ARG DOCKER_CHANNEL=stable
 ARG DOCKER_VERSION=19.03.13
 ARG DUMB_INIT_VERSION=1.2.5
@@ -60,7 +60,7 @@ RUN adduser --disabled-password --gecos "" --uid 1000 runner \
 RUN export ARCH=$(echo ${TARGETPLATFORM} | cut -d / -f2) \
     && if [ "$ARCH" = "arm64" ]; then export ARCH=aarch64 ; fi \
     && if [ "$ARCH" = "amd64" ] || [ "$ARCH" = "i386" ]; then export ARCH=x86_64 ; fi \
-	&& if ! curl -L -o docker.tgz "https://download.docker.com/linux/static/${DOCKER_CHANNEL}/${ARCH}/docker-${DOCKER_VERSION}.tgz"; then \
+	&& if ! curl -f -L -o docker.tgz "https://download.docker.com/linux/static/${DOCKER_CHANNEL}/${ARCH}/docker-${DOCKER_VERSION}.tgz"; then \
 		echo >&2 "error: failed to download 'docker-${DOCKER_VERSION}' from '${DOCKER_CHANNEL}' for '${ARCH}'"; \
 		exit 1; \
 	fi; \
@@ -86,7 +86,7 @@ RUN export ARCH=$(echo ${TARGETPLATFORM} | cut -d / -f2) \
     && if [ "$ARCH" = "amd64" ] || [ "$ARCH" = "x86_64" ] || [ "$ARCH" = "i386" ]; then export ARCH=x64 ; fi \
     && mkdir -p "$RUNNER_ASSETS_DIR" \
     && cd "$RUNNER_ASSETS_DIR" \
-    && curl -L -o runner.tar.gz https://github.com/actions/runner/releases/download/v${RUNNER_VERSION}/actions-runner-linux-${ARCH}-${RUNNER_VERSION}.tar.gz \
+    && curl -f -L -o runner.tar.gz https://github.com/actions/runner/releases/download/v${RUNNER_VERSION}/actions-runner-linux-${ARCH}-${RUNNER_VERSION}.tar.gz \
     && tar xzf ./runner.tar.gz \
     && rm runner.tar.gz \
     && ./bin/installdependencies.sh \
@@ -118,6 +118,7 @@ COPY --chown=runner:docker patched $RUNNER_ASSETS_DIR/patched
 
 # Add the Python "User Script Directory" to the PATH
 ENV PATH="${PATH}:${HOME}/.local/bin"
+ENV ImageOS=ubuntu20
 
 # No group definition, as that makes it harder to run docker.
 USER runner
diff --git a/runner/Dockerfile.ubuntu.1804 b/runner/Dockerfile.ubuntu.1804
index 3bc396ea..85d4f591 100644
--- a/runner/Dockerfile.ubuntu.1804
+++ b/runner/Dockerfile.ubuntu.1804
@@ -1,9 +1,9 @@
 FROM ubuntu:18.04
 
 ARG TARGETPLATFORM
-ARG RUNNER_VERSION=2.279.0
+ARG RUNNER_VERSION=2.280.2
 ARG DOCKER_CHANNEL=stable
-ARG DOCKER_VERSION=19.03.12
+ARG DOCKER_VERSION=20.10.8
 ARG DUMB_INIT_VERSION=1.2.5
 
 RUN test -n "$TARGETPLATFORM" || (echo "TARGETPLATFORM must be set" && false)
@@ -56,7 +56,7 @@ RUN set -vx; \
     export ARCH=$(echo ${TARGETPLATFORM} | cut -d / -f2) \
     && if [ "$ARCH" = "arm64" ]; then export ARCH=aarch64 ; fi \
     && if [ "$ARCH" = "amd64" ] || [ "$ARCH" = "i386" ]; then export ARCH=x86_64 ; fi \
-    && curl -L -o docker.tgz https://download.docker.com/linux/static/${DOCKER_CHANNEL}/${ARCH}/docker-${DOCKER_VERSION}.tgz \
+    && curl -f -L -o docker.tgz https://download.docker.com/linux/static/${DOCKER_CHANNEL}/${ARCH}/docker-${DOCKER_VERSION}.tgz \
     && tar zxvf docker.tgz \
     && install -o root -g root -m 755 docker/docker /usr/local/bin/docker \
     && rm -rf docker docker.tgz \
@@ -78,7 +78,7 @@ RUN export ARCH=$(echo ${TARGETPLATFORM} | cut -d / -f2) \
     && if [ "$ARCH" = "amd64" ] || [ "$ARCH" = "x86_64" ] || [ "$ARCH" = "i386" ]; then export ARCH=x64 ; fi \
     && mkdir -p "$RUNNER_ASSETS_DIR" \
     && cd "$RUNNER_ASSETS_DIR" \
-    && curl -L -o runner.tar.gz https://github.com/actions/runner/releases/download/v${RUNNER_VERSION}/actions-runner-linux-${ARCH}-${RUNNER_VERSION}.tar.gz \
+    && curl -f -L -o runner.tar.gz https://github.com/actions/runner/releases/download/v${RUNNER_VERSION}/actions-runner-linux-${ARCH}-${RUNNER_VERSION}.tar.gz \
     && tar xzf ./runner.tar.gz \
     && rm runner.tar.gz \
     && ./bin/installdependencies.sh \
@@ -96,7 +96,9 @@ COPY --chown=runner:docker patched $RUNNER_ASSETS_DIR/patched
 
 # Add the Python "User Script Directory" to the PATH
 ENV PATH="${PATH}:${HOME}/.local/bin"
+ENV ImageOS=ubuntu20
 
 USER runner
+
 ENTRYPOINT ["/usr/local/bin/dumb-init", "--"]
 CMD ["/entrypoint.sh"]
diff --git a/runner/Makefile b/runner/Makefile
index 7dced1e4..725ddf07 100644
--- a/runner/Makefile
+++ b/runner/Makefile
@@ -2,8 +2,8 @@ NAME ?= summerwind/actions-runner
 DIND_RUNNER_NAME ?= ${NAME}-dind
 TAG ?= latest
 
-RUNNER_VERSION ?= 2.279.0
-DOCKER_VERSION ?= 19.03.12
+RUNNER_VERSION ?= 2.280.2
+DOCKER_VERSION ?= 20.10.8
 
 # default list of platforms for which multiarch image is built
 ifeq (${PLATFORMS}, )