diff --git a/test/new-e2e/tests/agent-subcommands/health/health_win_test.go b/test/new-e2e/tests/agent-subcommands/health/health_win_test.go
index 0bc152a9818c5..a288c25e5d160 100644
--- a/test/new-e2e/tests/agent-subcommands/health/health_win_test.go
+++ b/test/new-e2e/tests/agent-subcommands/health/health_win_test.go
@@ -7,6 +7,7 @@ package health
 
 import (
 	"testing"
+	"time"
 
 	"github.com/DataDog/datadog-agent/test/fakeintake/api"
 	"github.com/DataDog/datadog-agent/test/new-e2e/pkg/e2e"
@@ -15,6 +16,7 @@ import (
 	"github.com/DataDog/test-infra-definitions/components/os"
 	"github.com/DataDog/test-infra-definitions/scenarios/aws/ec2"
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 )
 
 type windowsHealthSuite struct {
@@ -38,11 +40,10 @@ func (v *windowsHealthSuite) TestDefaultInstallUnhealthy() {
 	v.UpdateEnv(awshost.Provisioner(awshost.WithEC2InstanceOptions(ec2.WithOS(os.WindowsDefault)),
 		awshost.WithAgentOptions(agentparams.WithAgentConfig("log_level: info\n"))))
 
-	// agent should be unhealthy because the key is invalid
-	_, err := v.Env().Agent.Client.Health()
-	if err == nil {
-		assert.Fail(v.T(), "agent expected to be unhealthy, but no error found!")
-		return
-	}
-	assert.Contains(v.T(), err.Error(), "Agent health: FAIL")
+	require.EventuallyWithT(v.T(), func(collect *assert.CollectT) {
+		// forwarder should be unhealthy because the key is invalid
+		_, err := v.Env().Agent.Client.Health()
+		assert.ErrorContains(collect, err, "Agent health: FAIL")
+		assert.ErrorContains(collect, err, "=== 1 unhealthy components ===\nforwarder")
+	}, time.Second*30, time.Second)
 }