diff --git a/cmd/kubeadm/app/constants/constants.go b/cmd/kubeadm/app/constants/constants.go
index 62f08a61c3a..8d5cea7a985 100644
--- a/cmd/kubeadm/app/constants/constants.go
+++ b/cmd/kubeadm/app/constants/constants.go
@@ -44,6 +44,8 @@ const (
 	// should be joined with KubernetesDir.
 	TempDirForKubeadm = "tmp"
 
+	// CertificateBackdate defines the offset applied to notBefore for CA certificates generated by kubeadm
+	CertificateBackdate = time.Minute * 5
 	// CertificateValidity defines the validity for all the signed certificates generated by kubeadm
 	CertificateValidity = time.Hour * 24 * 365
 
diff --git a/cmd/kubeadm/app/util/pkiutil/pki_helpers.go b/cmd/kubeadm/app/util/pkiutil/pki_helpers.go
index 7887a2fbac3..dc78d1b3f6b 100644
--- a/cmd/kubeadm/app/util/pkiutil/pki_helpers.go
+++ b/cmd/kubeadm/app/util/pkiutil/pki_helpers.go
@@ -74,6 +74,8 @@ func NewCertificateAuthority(config *CertConfig) (*x509.Certificate, crypto.Sign
 		return nil, nil, errors.Wrap(err, "unable to create private key while generating CA certificate")
 	}
 
+	// backdate CA certificate to allow small time jumps
+	config.Config.NotBefore = time.Now().Add(-kubeadmconstants.CertificateBackdate)
 	cert, err := certutil.NewSelfSignedCACert(config.Config, key)
 	if err != nil {
 		return nil, nil, errors.Wrap(err, "unable to create self-signed CA certificate")
diff --git a/staging/src/k8s.io/client-go/util/cert/cert.go b/staging/src/k8s.io/client-go/util/cert/cert.go
index 37b023ef25d..91e171271af 100644
--- a/staging/src/k8s.io/client-go/util/cert/cert.go
+++ b/staging/src/k8s.io/client-go/util/cert/cert.go
@@ -45,6 +45,7 @@ type Config struct {
 	Organization []string
 	AltNames     AltNames
 	Usages       []x509.ExtKeyUsage
+	NotBefore    time.Time
 }
 
 // AltNames contains the domain names and IP addresses that will be added
@@ -64,6 +65,10 @@ func NewSelfSignedCACert(cfg Config, key crypto.Signer) (*x509.Certificate, erro
 		return nil, err
 	}
 	serial = new(big.Int).Add(serial, big.NewInt(1))
+	notBefore := now.UTC()
+	if !cfg.NotBefore.IsZero() {
+		notBefore = cfg.NotBefore.UTC()
+	}
 	tmpl := x509.Certificate{
 		SerialNumber: serial,
 		Subject: pkix.Name{
@@ -71,7 +76,7 @@ func NewSelfSignedCACert(cfg Config, key crypto.Signer) (*x509.Certificate, erro
 			Organization: cfg.Organization,
 		},
 		DNSNames:              []string{cfg.CommonName},
-		NotBefore:             now.UTC(),
+		NotBefore:             notBefore,
 		NotAfter:              now.Add(duration365d * 10).UTC(),
 		KeyUsage:              x509.KeyUsageKeyEncipherment | x509.KeyUsageDigitalSignature | x509.KeyUsageCertSign,
 		BasicConstraintsValid: true,