diff --git a/agent/app/healthcheck.go b/agent/app/healthcheck.go
index 9d5ba5063a2..0ff731a20c0 100644
--- a/agent/app/healthcheck.go
+++ b/agent/app/healthcheck.go
@@ -15,16 +15,25 @@ package app
 
 import (
 	"net/http"
+	"time"
 
 	"github.com/aws/amazon-ecs-agent/agent/sighandlers/exitcodes"
 	"github.com/cihub/seelog"
 )
 
 // runHealthcheck runs the Agent's healthcheck
-func runHealthcheck() int {
-	_, err := http.Get("http://localhost:51678/v1/metadata")
+func runHealthcheck(url string, timeout time.Duration) int {
+	client := &http.Client{
+		Timeout: timeout,
+	}
+	r, err := http.NewRequest("GET", url, nil)
+	if err != nil {
+		seelog.Errorf("error creating healthcheck request: %v", err)
+		return exitcodes.ExitError
+	}
+	_, err = client.Do(r)
 	if err != nil {
-		seelog.Warnf("Health check failed with error: %v", err)
+		seelog.Errorf("health check [GET %s] failed with error: %v", url, err)
 		return exitcodes.ExitError
 	}
 	return exitcodes.ExitSuccess
diff --git a/agent/app/healthcheck_test.go b/agent/app/healthcheck_test.go
new file mode 100644
index 00000000000..2fd489d0307
--- /dev/null
+++ b/agent/app/healthcheck_test.go
@@ -0,0 +1,64 @@
+// Copyright Amazon.com Inc. or its affiliates. All Rights Reserved.
+//
+// Licensed under the Apache License, Version 2.0 (the "License"). You may
+// not use this file except in compliance with the License. A copy of the
+// License is located at
+//
+//	http://aws.amazon.com/apache2.0/
+//
+// or in the "license" file accompanying this file. This file is distributed
+// on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either
+// express or implied. See the License for the specific language governing
+// permissions and limitations under the License.
+
+package app
+
+import (
+	"fmt"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestHealthcheck_Sunny(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		fmt.Fprintln(w, "Hello, client")
+	}))
+	defer ts.Close()
+
+	rc := runHealthcheck(ts.URL, time.Second*2)
+	require.Equal(t, 0, rc)
+}
+
+func TestHealthcheck_InvalidURL2(t *testing.T) {
+	// leading space in url is invalid
+	rc := runHealthcheck("  http://foobar", time.Second*2)
+	require.Equal(t, 1, rc)
+}
+
+func TestHealthcheck_Timeout(t *testing.T) {
+	sema := make(chan int)
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		<-sema
+	}))
+	defer ts.Close()
+
+	rc := runHealthcheck(ts.URL, time.Second*2)
+	require.Equal(t, 1, rc)
+	close(sema)
+}
+
+// we actually pass the healthcheck in the event of a non-200 http status code.
+func TestHealthcheck_404(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusNotFound)
+		w.Write([]byte("https://http.cat/404"))
+	}))
+	defer ts.Close()
+
+	rc := runHealthcheck(ts.URL+"/foobar", time.Second*2)
+	require.Equal(t, 0, rc)
+}
diff --git a/agent/app/run.go b/agent/app/run.go
index 8ba5f579e2f..134ba43c556 100644
--- a/agent/app/run.go
+++ b/agent/app/run.go
@@ -15,6 +15,7 @@ package app
 
 import (
 	"context"
+	"time"
 
 	"github.com/aws/amazon-ecs-agent/agent/app/args"
 	"github.com/aws/amazon-ecs-agent/agent/logger"
@@ -39,7 +40,11 @@ func Run(arguments []string) int {
 	} else if *parsedArgs.Version {
 		return version.PrintVersion()
 	} else if *parsedArgs.Healthcheck {
-		return runHealthcheck()
+		// Timeout is purposely set to shorter than the default docker healthcheck
+		// timeout of 30s. This is so that we can catch any http timeout and log the
+		// issue within agent logs.
+		// see https://docs.docker.com/engine/reference/builder/#healthcheck
+		return runHealthcheck("http://localhost:51678/v1/metadata", time.Second*25)
 	}
 
 	logger.SetLevel(*parsedArgs.LogLevel)
diff --git a/agent/tcs/handler/handler.go b/agent/tcs/handler/handler.go
index d367a24f1f8..b2351ced7cc 100644
--- a/agent/tcs/handler/handler.go
+++ b/agent/tcs/handler/handler.go
@@ -87,6 +87,11 @@ func StartSession(params *TelemetrySessionParams, statsEngine stats.Engine) erro
 			seelog.Errorf("Error: lost websocket connection with ECS Telemetry service (TCS): %v", tcsError)
 			params.time().Sleep(backoff.Duration())
 		}
+		select {
+		case <-params.Ctx.Done():
+			return nil
+		default:
+		}
 	}
 }