diff --git a/test/e2e/fixtures/yaml/podvm/podvm.yaml.in b/test/e2e/fixtures/yaml/podvm/podvm.yaml.in
index d5d88195a8..48e7f76f0e 100644
--- a/test/e2e/fixtures/yaml/podvm/podvm.yaml.in
+++ b/test/e2e/fixtures/yaml/podvm/podvm.yaml.in
@@ -42,8 +42,21 @@ spec:
       args:
         - |
           rm -f /etc/yum.repos.d/photon-updates.repo /etc/yum.repos.d/photon-extras.repo
-          yum install -y iputils openssh-server sshpass
-          mkdir /root/.ssh
+          mkdir -p /root/.ssh
+
+          attempt=0
+          max_attempts=10
+          until yum install -y iputils openssh-server sshpass >>/root/.install.log 2>&1; do
+            attempt=$((attempt + 1))
+            if [ "$attempt" -ge "$max_attempts" ]; then
+              echo "yum install failed after ${attempt} attempts" >>/root/.install.log
+              echo "failed" > /root/.failed
+              while true; do sleep 30; done
+            fi
+            echo "yum install attempt ${attempt} failed, retrying in 15s..." >>/root/.install.log
+            sleep 15
+          done
+
           echo > /root/.completed
           while true; do sleep 30; done
       {{- if or .PrivateKeySecretName .CustomUserPrivateKeySecretName }}
diff --git a/test/e2e/vmservice/vmservice/util.go b/test/e2e/vmservice/vmservice/util.go
index c1b4bc46c3..23129a8c10 100644
--- a/test/e2e/vmservice/vmservice/util.go
+++ b/test/e2e/vmservice/vmservice/util.go
@@ -678,11 +678,20 @@ func VerifyLoginAndRunCmdsInNSXSetup(ctx context.Context, config *config.E2EConf
 	namespace string, podVMName string, vmIP string, cmds []string, expectedOutput []string) {
 	framework.Logf("will attempt to ssh into %s using jumpbox podvm", vmIP)
 
-	Eventually(func() bool {
+	Eventually(func(g Gomega) bool {
 		stdout, err := clusterProxy.Exec(ctx, "-it", "jumpbox", "-n", namespace, "--", "sshpass", "-V")
 		if err == nil && stdout != nil {
 			return true
 		}
+
+		// The install script on the jumpbox PodVM marks /root/.failed once it gives
+		// up retrying yum install; fail fast with the real error instead of burning
+		// the full timeout on a install that will never succeed.
+		if failMarker, ferr := clusterProxy.Exec(ctx, "jumpbox", "-n", namespace, "--", "cat", "/root/.failed"); ferr == nil && len(failMarker) > 0 {
+			installLog, _ := clusterProxy.Exec(ctx, "jumpbox", "-n", namespace, "--", "cat", "/root/.install.log")
+			g.Expect(false).To(BeTrue(), "jumpbox PodVM failed to install sshpass permanently:\n%s", string(installLog))
+		}
+
 		// The Exec function will output an error message on each failure.
 		// Add a log here to clarify that retries are expected behavior.
 		framework.Logf("sshpass not yet installed on jumpbox PodVM, retrying...")