diff --git a/cmd/cloudflared/tunnel/cmd.go b/cmd/cloudflared/tunnel/cmd.go
index 8994e3ad..4c5a41b5 100644
--- a/cmd/cloudflared/tunnel/cmd.go
+++ b/cmd/cloudflared/tunnel/cmd.go
@@ -339,7 +339,9 @@ func StartServer(
 		errC <- metrics.ServeMetrics(metricsListener, shutdownC, readinessCh, log)
 	}()
 
-	ingressRules.StartOrigins(&wg, log, shutdownC, errC)
+	if err := ingressRules.StartOrigins(&wg, log, shutdownC, errC); err != nil {
+		return err
+	}
 
 	reconnectCh := make(chan origin.ReconnectSignal, 1)
 	if c.IsSet("stdin-control") {
diff --git a/ingress/ingress.go b/ingress/ingress.go
index dcf70ae1..eeaa2184 100644
--- a/ingress/ingress.go
+++ b/ingress/ingress.go
@@ -113,12 +113,18 @@ func (ing Ingress) IsEmpty() bool {
 }
 
 // StartOrigins will start any origin services managed by cloudflared, e.g. proxy servers or Hello World.
-func (ing Ingress) StartOrigins(wg *sync.WaitGroup, log *zerolog.Logger, shutdownC <-chan struct{}, errC chan error) {
+func (ing Ingress) StartOrigins(
+	wg *sync.WaitGroup,
+	log *zerolog.Logger,
+	shutdownC <-chan struct{},
+	errC chan error,
+) error {
 	for _, rule := range ing.Rules {
 		if err := rule.Service.start(wg, log, shutdownC, errC, rule.Config); err != nil {
-			log.Error().Msgf("Error starting local service %s: %s", rule.Service, err)
+			return errors.Wrapf(err, "Error starting local service %s", rule.Service)
 		}
 	}
+	return nil
 }
 
 // CatchAll returns the catch-all rule (i.e. the last rule)
diff --git a/origin/proxy_test.go b/origin/proxy_test.go
index 6e07a559..193764f0 100644
--- a/origin/proxy_test.go
+++ b/origin/proxy_test.go
@@ -123,7 +123,7 @@ func TestProxySingleOrigin(t *testing.T) {
 
 	var wg sync.WaitGroup
 	errC := make(chan error)
-	ingressRule.StartOrigins(&wg, &log, ctx.Done(), errC)
+	require.NoError(t, ingressRule.StartOrigins(&wg, &log, ctx.Done(), errC))
 
 	client := NewClient(ingressRule, testTags, &log)
 	t.Run("testProxyHTTP", testProxyHTTP(t, client))
@@ -256,7 +256,7 @@ func TestProxyMultipleOrigins(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	errC := make(chan error)
 	var wg sync.WaitGroup
-	ingress.StartOrigins(&wg, &log, ctx.Done(), errC)
+	require.NoError(t, ingress.StartOrigins(&wg, &log, ctx.Done(), errC))
 
 	client := NewClient(ingress, testTags, &log)