diff --git a/pkg/webhook/init_cert.go b/pkg/webhook/init_cert.go
index b37c127a7..dc002fd21 100644
--- a/pkg/webhook/init_cert.go
+++ b/pkg/webhook/init_cert.go
@@ -162,7 +162,7 @@ func createCerts(serviceName string, serviceNamespace string) (certs webhookCert
 			Organization: []string{"flyte.org"},
 		},
 		NotBefore:             time.Now(),
-		NotAfter:              time.Now().AddDate(1, 0, 0),
+		NotAfter:              time.Now().AddDate(99, 0, 0),
 		IsCA:                  true,
 		ExtKeyUsage:           []x509.ExtKeyUsage{x509.ExtKeyUsageClientAuth, x509.ExtKeyUsageServerAuth},
 		KeyUsage:              x509.KeyUsageDigitalSignature | x509.KeyUsageCertSign,
@@ -204,7 +204,7 @@ func createCerts(serviceName string, serviceNamespace string) (certs webhookCert
 			Organization: []string{"flyte.org"},
 		},
 		NotBefore:    time.Now(),
-		NotAfter:     time.Now().AddDate(1, 0, 0),
+		NotAfter:     time.Now().AddDate(99, 0, 0),
 		SubjectKeyId: []byte{1, 2, 3, 4, 6},
 		ExtKeyUsage:  []x509.ExtKeyUsage{x509.ExtKeyUsageClientAuth, x509.ExtKeyUsageServerAuth},
 		KeyUsage:     x509.KeyUsageDigitalSignature,