diff --git a/.github/workflows/docker-in-docker-stress-test.yaml b/.github/workflows/docker-in-docker-stress-test.yaml
new file mode 100644
index 000000000..d561a19e9
--- /dev/null
+++ b/.github/workflows/docker-in-docker-stress-test.yaml
@@ -0,0 +1,23 @@
+name: "Stress test - Docker in Docker"
+on:
+  pull_request:
+    paths:
+      - 'src/docker-in-docker/**'
+  workflow_dispatch:
+
+jobs:
+  test:
+    strategy:
+      matrix:
+        test-pass: [ 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20 ]
+      fail-fast: false
+    runs-on: ubuntu-latest
+    continue-on-error: true
+    steps:
+      - uses: actions/checkout@v3
+
+      - name: "Install latest devcontainer CLI"
+        run: npm install -g @devcontainers/cli
+
+      - name: "Generating tests for 'docker-in-docker' which validates if docker daemon is available within 'onCreateCommand'"
+        run: devcontainer features test --skip-scenarios -f docker-in-docker -i mcr.microsoft.com/devcontainers/base:debian .
diff --git a/src/docker-in-docker/install.sh b/src/docker-in-docker/install.sh
index bdef12697..d55c45153 100755
--- a/src/docker-in-docker/install.sh
+++ b/src/docker-in-docker/install.sh
@@ -423,12 +423,35 @@ dockerd_start="AZURE_DNS_AUTO_DETECTION=${AZURE_DNS_AUTO_DETECTION} DOCKER_DEFAU
 INNEREOF
 )"
 
-# Start using sudo if not invoked as root
-if [ "$(id -u)" -ne 0 ]; then
-    sudo /bin/sh -c "${dockerd_start}"
-else
-    eval "${dockerd_start}"
-fi
+retry_docker_start_count=0
+docker_ok="false"
+
+until [ "${docker_ok}" = "true"  ] || [ "${retry_docker_start_count}" -eq "5" ];
+do 
+    # Start using sudo if not invoked as root
+    if [ "$(id -u)" -ne 0 ]; then
+        sudo /bin/sh -c "${dockerd_start}"
+    else
+        eval "${dockerd_start}"
+    fi
+
+    retry_count=0
+    until [ "${docker_ok}" = "true"  ] || [ "${retry_count}" -eq "5" ];
+    do
+        set +e
+            docker info > /dev/null 2>&1 && docker_ok="true"
+        set -e
+
+        retry_count=`expr $retry_count + 1`
+        sleep 1s
+    done
+    
+    if [ "${docker_ok}" != "true" ]; then
+        echo "(*) Failed to start docker, retrying..."
+    fi
+    
+    retry_docker_start_count=`expr $retry_docker_start_count + 1`
+done
 
 # Execute whatever commands were passed in (if any). This allows us
 # to set this script to ENTRYPOINT while still executing the default CMD.
diff --git a/test/docker-in-docker/test.sh b/test/docker-in-docker/test.sh
index 1eebfd243..b25124cc3 100755
--- a/test/docker-in-docker/test.sh
+++ b/test/docker-in-docker/test.sh
@@ -8,10 +8,11 @@ source dev-container-features-test-lib
 # Feature specific tests
 check "version" docker  --version
 check "docker-init-exists" bash -c "ls /usr/local/share/docker-init.sh"
+check "docker-ps" bash -c "docker ps"
 check "log-exists" bash -c "ls /tmp/dockerd.log"
 check "log-for-completion" bash -c "cat /tmp/dockerd.log | grep 'Daemon has completed initialization'"
 check "log-contents" bash -c "cat /tmp/dockerd.log | grep 'API listen on /var/run/docker.sock'"
-check "docker-ps" bash -c "docker ps"
+
 
 # Report result
-reportResults
\ No newline at end of file
+reportResults