diff --git a/src/Misc/layoutroot/run-helper.cmd.template b/src/Misc/layoutroot/run-helper.cmd.template
new file mode 100644
index 00000000000..562038336dd
--- /dev/null
+++ b/src/Misc/layoutroot/run-helper.cmd.template
@@ -0,0 +1,39 @@
+@echo off
+
+"%~dp0\bin\Runner.Listener.exe" run %*
+
+rem using `if %ERRORLEVEL% EQU N` insterad of `if ERRORLEVEL N`
+rem `if ERRORLEVEL N` means: error level is N or MORE
+  
+if %ERRORLEVEL% EQU 0 (
+  echo "Runner listener exit with 0 return code, stop the service, no retry needed."
+  exit /b 0
+)
+
+if %ERRORLEVEL% EQU 1 (
+  echo "Runner listener exit with terminated error, stop the service, no retry needed."
+  exit /b 0
+)
+
+if %ERRORLEVEL% EQU 2 (
+  echo "Runner listener exit with retryable error, re-launch runner in 5 seconds."
+  ping 127.0.0.1 -n 6 -w 1000 >NUL
+  exit /b 1
+)
+
+if %ERRORLEVEL% EQU 3 (
+  rem Sleep 5 seconds to wait for the runner update process finish
+  echo "Runner listener exit because of updating, re-launch runner in 5 seconds"
+  ping 127.0.0.1 -n 6 -w 1000 >NUL
+  exit /b 1
+)
+
+if %ERRORLEVEL% EQU 4 (
+  rem Sleep 5 seconds to wait for the ephemeral runner update process finish
+  echo "Runner listener exit because of updating, re-launch ephemeral runner in 5 seconds"
+  ping 127.0.0.1 -n 6 -w 1000 >NUL
+  exit /b 1
+)
+
+echo "Exiting after unknown error code: %ERRORLEVEL%"
+exit /b 0
\ No newline at end of file
diff --git a/src/Misc/layoutroot/run-helper.sh.template b/src/Misc/layoutroot/run-helper.sh.template
new file mode 100755
index 00000000000..ef54bd516b0
--- /dev/null
+++ b/src/Misc/layoutroot/run-helper.sh.template
@@ -0,0 +1,54 @@
+#!/bin/bash
+
+# Validate not sudo
+user_id=`id -u`
+if [ $user_id -eq 0 -a -z "$RUNNER_ALLOW_RUNASROOT" ]; then
+    echo "Must not run interactively with sudo"
+    exit 1
+fi
+
+# Run
+shopt -s nocasematch
+
+safe_sleep() {
+    if [ ! -x "$(command -v sleep)" ]; then
+        if [ ! -x "$(command -v ping)" ]; then
+            COUNT="0"
+            while [[ $COUNT != 5000 ]]; do
+                echo "SLEEP" > /dev/null
+                COUNT=$[$COUNT+1]
+            done
+        else
+            ping -c 5 127.0.0.1 > /dev/null
+        fi
+    else
+        sleep 5
+    fi
+}
+
+bin/Runner.Listener run $*
+returnCode=$?
+if [[ $returnCode == 0 ]]; then
+    echo "Runner listener exit with 0 return code, stop the service, no retry needed."
+    exit 0
+elif [[ $returnCode == 1 ]]; then
+    echo "Runner listener exit with terminated error, stop the service, no retry needed."
+    exit 0
+elif [[ $returnCode == 2 ]]; then
+    echo "Runner listener exit with retryable error, re-launch runner in 5 seconds."
+    safe_sleep
+    exit 1
+elif [[ $returnCode == 3 ]]; then
+    # Sleep 5 seconds to wait for the runner update process finish
+    echo "Runner listener exit because of updating, re-launch runner in 5 seconds"
+    safe_sleep
+    exit 1
+elif [[ $returnCode == 4 ]]; then
+    # Sleep 5 seconds to wait for the ephemeral runner update process finish
+    echo "Runner listener exit because of updating, re-launch ephemeral runner in 5 seconds"
+    safe_sleep
+    exit 1
+else
+    echo "Exiting with unknown error code: ${returnCode}"
+    exit 0
+fi
diff --git a/src/Misc/layoutroot/run.cmd b/src/Misc/layoutroot/run.cmd
index df5fd390975..cd5cb68970d 100644
--- a/src/Misc/layoutroot/run.cmd
+++ b/src/Misc/layoutroot/run.cmd
@@ -13,21 +13,19 @@ if defined VERBOSE_ARG (
 rem Unblock files in the root of the layout folder. E.g. .cmd files.
 powershell.exe -NoLogo -Sta -NoProfile -NonInteractive -ExecutionPolicy Unrestricted -Command "$VerbosePreference = %VERBOSE_ARG% ; Get-ChildItem -LiteralPath '%~dp0' | ForEach-Object { Write-Verbose ('Unblock: {0}' -f $_.FullName) ; $_ } | Unblock-File | Out-Null"
 
-if /i "%~1" equ "localRun" (
-    rem ********************************************************************************
-    rem Local run.
-    rem ********************************************************************************
-    "%~dp0bin\Runner.Listener.exe" %*
-) else (
-  rem ********************************************************************************
-  rem Run.
-  rem ********************************************************************************
-  "%~dp0bin\Runner.Listener.exe" run %*
 
-  rem Return code 4 means the run once runner received an update message.
-  rem Sleep 5 seconds to wait for the update process finish and run the runner again.
-  if ERRORLEVEL 4 (
-    timeout /t 5 /nobreak > NUL
-    "%~dp0bin\Runner.Listener.exe" run %*
-  )
+rem ********************************************************************************
+rem Run.
+rem ********************************************************************************
+
+:launch_helper
+copy run-helper.cmd.template run-helper.cmd /Y
+call "%~dp0run-helper.cmd" %*
+  
+if %ERRORLEVEL% EQU 1 (
+  echo "Restarting runner..."
+  goto :launch_helper
+) else (  
+  echo "Exiting runner..."
+  exit 0
 )
diff --git a/src/Misc/layoutroot/run.sh b/src/Misc/layoutroot/run.sh
index 03bb10adcf8..580ab934f29 100755
--- a/src/Misc/layoutroot/run.sh
+++ b/src/Misc/layoutroot/run.sh
@@ -1,64 +1,24 @@
 #!/bin/bash
 
-# Validate not sudo
-user_id=`id -u`
-if [ $user_id -eq 0 -a -z "$RUNNER_ALLOW_RUNASROOT" ]; then
-    echo "Must not run interactively with sudo"
-    exit 1
-fi
-
 # Change directory to the script root directory
 # https://stackoverflow.com/questions/59895/getting-the-source-directory-of-a-bash-script-from-within
 SOURCE="${BASH_SOURCE[0]}"
 while [ -h "$SOURCE" ]; do # resolve $SOURCE until the file is no longer a symlink
-  DIR="$( cd -P "$( dirname "$SOURCE" )" && pwd )"
-  SOURCE="$(readlink "$SOURCE")"
-  [[ $SOURCE != /* ]] && SOURCE="$DIR/$SOURCE" # if $SOURCE was a relative symlink, we need to resolve it relative to the path where the symlink file was located
+    DIR="$( cd -P "$( dirname "$SOURCE" )" && pwd )"
+    SOURCE="$(readlink "$SOURCE")"
+    [[ $SOURCE != /* ]] && SOURCE="$DIR/$SOURCE" # if $SOURCE was a relative symlink, we need to resolve it relative to the path where the symlink file was located
 done
 DIR="$( cd -P "$( dirname "$SOURCE" )" && pwd )"
-
-# Do not "cd $DIR". For localRun, the current directory is expected to be the repo location on disk.
-
-# Run
-shopt -s nocasematch
-if [[ "$1" == "localRun" ]]; then
-    "$DIR"/bin/Runner.Listener $*
-else
-    "$DIR"/bin/Runner.Listener run $*
-
-# Return code 3 means the run once runner received an update message.
-# Sleep 5 seconds to wait for the update process finish
+cp -f run-helper.sh.template run-helper.sh
+# run the helper process which keep the listener alive
+while :;
+do
+    "$DIR"/run-helper.sh $*
     returnCode=$?
-    if [[ $returnCode == 3 ]]; then
-        if [ ! -x "$(command -v sleep)" ]; then
-            if [ ! -x "$(command -v ping)" ]; then
-                COUNT="0"
-                while [[ $COUNT != 5000 ]]; do
-                    echo "SLEEP" > /dev/null
-                    COUNT=$[$COUNT+1]
-                done
-            else
-                ping -c 5 127.0.0.1 > /dev/null
-            fi
-        else
-            sleep 5
-        fi
-    elif [[ $returnCode == 4 ]]; then
-        if [ ! -x "$(command -v sleep)" ]; then
-            if [ ! -x "$(command -v ping)" ]; then
-                COUNT="0"
-                while [[ $COUNT != 5000 ]]; do
-                    echo "SLEEP" > /dev/null
-                    COUNT=$[$COUNT+1]
-                done
-            else
-                ping -c 5 127.0.0.1 > /dev/null
-            fi
-        else
-            sleep 5
-        fi
-        "$DIR"/bin/Runner.Listener run $*
+    if [[ $returnCode == 1 ]]; then
+        echo "Restarting runner..."
     else
-        exit $returnCode
+        echo "Exiting runner..."
+        exit 0
     fi
-fi
+done
diff --git a/src/Runner.Listener/Configuration/ConfigurationManager.cs b/src/Runner.Listener/Configuration/ConfigurationManager.cs
index db6e84fee95..09de9ed1b4f 100644
--- a/src/Runner.Listener/Configuration/ConfigurationManager.cs
+++ b/src/Runner.Listener/Configuration/ConfigurationManager.cs
@@ -54,7 +54,7 @@ public RunnerSettings LoadSettings()
             Trace.Info(nameof(LoadSettings));
             if (!IsConfigured())
             {
-                throw new InvalidOperationException("Not configured. Run config.(sh/cmd) to configure the runner.");
+                throw new NonRetryableException("Not configured. Run config.(sh/cmd) to configure the runner.");
             }
 
             RunnerSettings settings = _store.GetSettings();
diff --git a/src/Runner.Listener/Runner.cs b/src/Runner.Listener/Runner.cs
index 89dcbb94a35..aa14776bf29 100644
--- a/src/Runner.Listener/Runner.cs
+++ b/src/Runner.Listener/Runner.cs
@@ -408,7 +408,7 @@ private async Task<int> RunAsync(RunnerSettings settings, bool runOnce = false)
                                     autoUpdateInProgress = true;
                                     var runnerUpdateMessage = JsonUtility.FromString<AgentRefreshMessage>(message.Body);
                                     var selfUpdater = HostContext.GetService<ISelfUpdater>();
-                                    selfUpdateTask = selfUpdater.SelfUpdate(runnerUpdateMessage, jobDispatcher, !runOnce && HostContext.StartupType != StartupType.Service, HostContext.RunnerShutdownToken);
+                                    selfUpdateTask = selfUpdater.SelfUpdate(runnerUpdateMessage, jobDispatcher, false, HostContext.RunnerShutdownToken);
                                     Trace.Info("Refresh message received, kick-off selfupdate background process.");
                                 }
                                 else