diff --git a/runner/entrypoint.sh b/runner/entrypoint.sh
index d220b517..e48966d9 100755
--- a/runner/entrypoint.sh
+++ b/runner/entrypoint.sh
@@ -1,23 +1,40 @@
 #!/bin/bash
 
+LIGHTGREEN="\e[0;32m"
+LIGHTRED="\e[0;31m"
+WHITE="\e[0;97m"
+RESET="\e[0m"
+
+log(){
+  echo -e "${WHITE}${@}${RESET}" 1>&2
+}
+
+success(){
+  echo -e "${LIGHTGREEN}${@}${RESET}" 1>&2
+}
+
+error(){
+  echo -e "${LIGHTRED}${@}${RESET}" 1>&2
+}
+
 if [ ! -z "${STARTUP_DELAY_IN_SECONDS}" ]; then
-  echo "Delaying startup by ${STARTUP_DELAY_IN_SECONDS} seconds" 1>&2
+  log "Delaying startup by ${STARTUP_DELAY_IN_SECONDS} seconds"
   sleep ${STARTUP_DELAY_IN_SECONDS}
 fi
 
 if [ -z "${GITHUB_URL}" ]; then
-  echo "Working with public GitHub" 1>&2
+  log "Working with public GitHub"
   GITHUB_URL="https://github.com/"
 else
   length=${#GITHUB_URL}
   last_char=${GITHUB_URL:length-1:1}
 
   [[ $last_char != "/" ]] && GITHUB_URL="$GITHUB_URL/"; :
-  echo "Github endpoint URL ${GITHUB_URL}"
+  log "Github endpoint URL ${GITHUB_URL}"
 fi
 
 if [ -z "${RUNNER_NAME}" ]; then
-  echo "RUNNER_NAME must be set" 1>&2
+  error "RUNNER_NAME must be set"
   exit 1
 fi
 
@@ -30,12 +47,12 @@ elif [ -n "${RUNNER_REPO}" ]; then
 elif [ -n "${RUNNER_ENTERPRISE}" ]; then
   ATTACH="enterprises/${RUNNER_ENTERPRISE}"
 else
-  echo "At least one of RUNNER_ORG or RUNNER_REPO or RUNNER_ENTERPRISE must be set" 1>&2
+  error "At least one of RUNNER_ORG or RUNNER_REPO or RUNNER_ENTERPRISE must be set"
   exit 1
 fi
 
 if [ -z "${RUNNER_TOKEN}" ]; then
-  echo "RUNNER_TOKEN must be set" 1>&2
+  error "RUNNER_TOKEN must be set"
   exit 1
 fi
 
@@ -45,7 +62,7 @@ fi
 
 # Hack due to https://github.com/actions-runner-controller/actions-runner-controller/issues/252#issuecomment-758338483
 if [ ! -d /runner ]; then
-  echo "/runner should be an emptyDir mount. Please fix the pod spec." 1>&2
+  error "/runner should be an emptyDir mount. Please fix the pod spec."
   exit 1
 fi
 
@@ -60,42 +77,56 @@ if [ "${RUNNER_FEATURE_FLAG_EPHEMERAL:-}" == "true" -a "${RUNNER_EPHEMERAL}" !=
   echo "Passing --ephemeral to config.sh to enable the ephemeral runner."
 fi
 
-./config.sh --unattended --replace \
-  --name "${RUNNER_NAME}" \
-  --url "${GITHUB_URL}${ATTACH}" \
-  --token "${RUNNER_TOKEN}" \
-  --runnergroup "${RUNNER_GROUPS}" \
-  --labels "${RUNNER_LABELS}" \
-  --work "${RUNNER_WORKDIR}" "${config_args[@]}"
+retries_left=10
+while [[ ${retries_left} -gt 0 ]]; do
+  log "Configuring the runner."
+  ./config.sh --unattended --replace \
+    --name "${RUNNER_NAME}" \
+    --url "${GITHUB_URL}${ATTACH}" \
+    --token "${RUNNER_TOKEN}" \
+    --runnergroup "${RUNNER_GROUPS}" \
+    --labels "${RUNNER_LABELS}" \
+    --work "${RUNNER_WORKDIR}" "${config_args[@]}"
 
-if [ -f /runner/.runner ]; then
-  echo Runner has successfully been configured with the following data.
-  cat /runner/.runner
-  # Note: the `.runner` file's content should be something like the below:
-  #
-  # $ cat /runner/.runner
-  # {
-  # "agentId": 117, #=> corresponds to the ID of the runner
-  # "agentName": "THE_RUNNER_POD_NAME",
-  # "poolId": 1,
-  # "poolName": "Default",
-  # "serverUrl": "https://pipelines.actions.githubusercontent.com/SOME_RANDOM_ID",
-  # "gitHubUrl": "https://github.com/USER/REPO",
-  # "workFolder": "/some/work/dir" #=> corresponds to Runner.Spec.WorkDir
-  # }
-  #
-  # Especially `agentId` is important, as other than listing all the runners in the repo,
-  # this is the only change we could get the exact runnner ID which can be useful for further
-  # GitHub API call like the below. Note that 171 is the agentId seen above.
-  #   curl \
-  #     -H "Accept: application/vnd.github.v3+json" \
-  #     -H "Authorization: bearer ${GITHUB_TOKEN}"
-  #     https://api.github.com/repos/USER/REPO/actions/runners/171
+  if [ -f /runner/.runner ]; then
+    success "Runner successfully configured."
+    break
+  fi
+
+  retries_left=$((retries_left - 1))
+  sleep 1
+done
+
+if [ ! -f /runner/.runner ]; then
+  # we couldn't configure and register the runner; no point continuing
+  error "Configuration failed!"
+  exit 2
 fi
 
+cat .runner
+# Note: the `.runner` file's content should be something like the below:
+#
+# $ cat /runner/.runner
+# {
+# "agentId": 117, #=> corresponds to the ID of the runner
+# "agentName": "THE_RUNNER_POD_NAME",
+# "poolId": 1,
+# "poolName": "Default",
+# "serverUrl": "https://pipelines.actions.githubusercontent.com/SOME_RANDOM_ID",
+# "gitHubUrl": "https://github.com/USER/REPO",
+# "workFolder": "/some/work/dir" #=> corresponds to Runner.Spec.WorkDir
+# }
+#
+# Especially `agentId` is important, as other than listing all the runners in the repo,
+# this is the only change we could get the exact runnner ID which can be useful for further
+# GitHub API call like the below. Note that 171 is the agentId seen above.
+#   curl \
+#     -H "Accept: application/vnd.github.v3+json" \
+#     -H "Authorization: bearer ${GITHUB_TOKEN}"
+#     https://api.github.com/repos/USER/REPO/actions/runners/171
+
 if [ -n "${RUNNER_REGISTRATION_ONLY}" ]; then
-  echo
-  echo "This runner is configured to be registration-only. Exiting without starting the runner service..."
+  success "This runner is configured to be registration-only. Exiting without starting the runner service..."
   exit 0
 fi