diff --git a/pkg/agent/config/config.go b/pkg/agent/config/config.go
index b4c38417d9..c37c25e49d 100644
--- a/pkg/agent/config/config.go
+++ b/pkg/agent/config/config.go
@@ -48,8 +48,8 @@ const (
 // so this is somewhat computationally expensive on the server side, and is retried with jitter
 // to avoid having clients hammer on the server at fixed periods.
 // A call to this will bock until agent configuration is successfully returned by the
-// server.
-func Get(ctx context.Context, agent cmds.Agent, proxy proxy.Proxy) *config.Node {
+// server, or the context is cancelled.
+func Get(ctx context.Context, agent cmds.Agent, proxy proxy.Proxy) (*config.Node, error) {
 	var agentConfig *config.Node
 	var err error
 
@@ -65,7 +65,7 @@ func Get(ctx context.Context, agent cmds.Agent, proxy proxy.Proxy) *config.Node
 			cancel()
 		}
 	}, 5*time.Second, 1.0, true)
-	return agentConfig
+	return agentConfig, err
 }
 
 // KubeProxyDisabled returns a bool indicating whether or not kube-proxy has been disabled in the
diff --git a/pkg/agent/run.go b/pkg/agent/run.go
index 242d201899..a050cc3031 100644
--- a/pkg/agent/run.go
+++ b/pkg/agent/run.go
@@ -52,7 +52,10 @@ import (
 )
 
 func run(ctx context.Context, cfg cmds.Agent, proxy proxy.Proxy) error {
-	nodeConfig := config.Get(ctx, cfg, proxy)
+	nodeConfig, err := config.Get(ctx, cfg, proxy)
+	if err != nil {
+		return errors.Wrap(err, "failed to retrieve agent configuration")
+	}
 
 	dualCluster, err := utilsnet.IsDualStackCIDRs(nodeConfig.AgentConfig.ClusterCIDRs)
 	if err != nil {
@@ -234,7 +237,11 @@ func RunStandalone(ctx context.Context, cfg cmds.Agent) error {
 		return err
 	}
 
-	nodeConfig := config.Get(ctx, cfg, proxy)
+	nodeConfig, err := config.Get(ctx, cfg, proxy)
+	if err != nil {
+		return errors.Wrap(err, "failed to retrieve agent configuration")
+	}
+
 	if err := executor.Bootstrap(ctx, nodeConfig, cfg); err != nil {
 		return err
 	}