diff --git a/test/e2e/windows/hybrid_network.go b/test/e2e/windows/hybrid_network.go
index 5e57a8c4c9d..7a133b29044 100644
--- a/test/e2e/windows/hybrid_network.go
+++ b/test/e2e/windows/hybrid_network.go
@@ -89,12 +89,14 @@ var (
 )
 
 func assertConsistentConnectivity(f *framework.Framework, podName string, os string, cmd []string) {
-	gomega.Consistently(func() error {
+	connChecker := func() error {
 		ginkgo.By(fmt.Sprintf("checking connectivity of %s-container in %s", os, podName))
 		// TODO, we should be retrying this similar to what is done in DialFromNode, in the test/e2e/networking/networking.go tests
 		_, _, err := f.ExecCommandInContainerWithFullOutput(podName, os+"-container", cmd...)
 		return err
-	}, duration, pollInterval).ShouldNot(gomega.HaveOccurred())
+	}
+	gomega.Eventually(connChecker, duration, pollInterval).ShouldNot(gomega.HaveOccurred())
+	gomega.Consistently(connChecker, duration, pollInterval).ShouldNot(gomega.HaveOccurred())
 }
 
 func linuxCheck(address string, port int) []string {