diff --git a/pkg/controller/certificates/issuing/issuing_controller.go b/pkg/controller/certificates/issuing/issuing_controller.go
index ab0fc05bf..92f66d4ef 100644
--- a/pkg/controller/certificates/issuing/issuing_controller.go
+++ b/pkg/controller/certificates/issuing/issuing_controller.go
@@ -236,6 +236,24 @@ func (c *controller) ProcessItem(ctx context.Context, key string) error {
 		return nil
 	}
 
+	certIssuingCond := apiutil.GetCertificateCondition(crt, cmapi.CertificateConditionIssuing)
+	crReadyCond := apiutil.GetCertificateRequestCondition(req, cmapi.CertificateRequestConditionReady)
+	if certIssuingCond == nil {
+		// This should never happen
+		log.V(logf.ErrorLevel).Info("Certificate does not have an issuing condition")
+		return nil
+	}
+	// If the CertificateRequest for this revision has failed, but before the
+	// Issuing condition was set on the Certificate, then it must be a
+	// failed CertificateRequest from previous issuance for the same
+	// revision. Leave it to certificate-requests controller to delete the
+	// CertificateRequest and create a new one.
+	if req.Status.FailureTime != nil &&
+		req.Status.FailureTime.Before(certIssuingCond.LastTransitionTime) && crReadyCond.Reason == cmapi.CertificateRequestReasonFailed {
+		log.V(logf.InfoLevel).Info("Found a failed CertificateRequest from previous issuance, waiting for it to be deleted...")
+		return nil
+	}
+
 	// Some issuers won't honor the "Denied=True" condition, and we don't want
 	// to break these issuers. To avoid breaking these issuers, we skip bubbling
 	// up the "Denied=True" condition from the certificate request object to the
@@ -246,8 +264,7 @@ func (c *controller) ProcessItem(ctx context.Context, key string) error {
 	// certificate request is "Denied=True" and that the issuer still proceeds
 	// to adding the "Ready" condition (to either true or false), then we
 	// consider that this issuer has ignored the "Denied" state.
-	cond := apiutil.GetCertificateRequestCondition(req, cmapi.CertificateRequestConditionReady)
-	if cond == nil {
+	if crReadyCond == nil {
 		if apiutil.CertificateRequestIsDenied(req) {
 			return c.failIssueCertificate(ctx, log, crt, apiutil.GetCertificateRequestCondition(req, cmapi.CertificateRequestConditionDenied))
 		}
@@ -258,7 +275,7 @@ func (c *controller) ProcessItem(ctx context.Context, key string) error {
 
 	// If the certificate request has failed, set the last failure time to now,
 	// and set the Issuing status condition to False with reason.
-	if cond.Reason == cmapi.CertificateRequestReasonFailed {
+	if crReadyCond.Reason == cmapi.CertificateRequestReasonFailed {
 		return c.failIssueCertificate(ctx, log, crt, apiutil.GetCertificateRequestCondition(req, cmapi.CertificateRequestConditionReady))
 	}
 
@@ -278,7 +295,7 @@ func (c *controller) ProcessItem(ctx context.Context, key string) error {
 
 	// If the CertificateRequest is valid and ready, verify its status and issue
 	// accordingly.
-	if cond.Reason == cmapi.CertificateRequestReasonIssued {
+	if crReadyCond.Reason == cmapi.CertificateRequestReasonIssued {
 		return c.issueCertificate(ctx, nextRevision, crt, req, pk)
 	}
 
@@ -290,7 +307,7 @@ func (c *controller) ProcessItem(ctx context.Context, key string) error {
 	}
 
 	// CertificateRequest is not in a final state so do nothing.
-	log.V(logf.DebugLevel).Info("CertificateRequest not in final state, waiting...", "reason", cond.Reason)
+	log.V(logf.DebugLevel).Info("CertificateRequest not in final state, waiting...", "reason", crReadyCond.Reason)
 	return nil
 }
 
diff --git a/pkg/controller/certificates/issuing/issuing_controller_test.go b/pkg/controller/certificates/issuing/issuing_controller_test.go
index 1c2f4fe88..fd47f8523 100644
--- a/pkg/controller/certificates/issuing/issuing_controller_test.go
+++ b/pkg/controller/certificates/issuing/issuing_controller_test.go
@@ -71,17 +71,17 @@ func TestIssuingController(t *testing.T) {
 	exampleBundle := internaltest.MustCreateCryptoBundle(t, baseCert.DeepCopy(), fixedClock)
 
 	exampleBundleAlt := internaltest.MustCreateCryptoBundle(t, baseCert.DeepCopy(), fixedClock)
+	metaFixedClockStart := metav1.NewTime(fixedClockStart)
 
 	issuingCert := gen.CertificateFrom(baseCert.DeepCopy(),
 		gen.SetCertificateStatusCondition(cmapi.CertificateCondition{
 			Type:               cmapi.CertificateConditionIssuing,
 			Status:             cmmeta.ConditionTrue,
 			ObservedGeneration: 3,
+			LastTransitionTime: &metaFixedClockStart,
 		}),
 	)
 
-	metaFixedClockStart := metav1.NewTime(fixedClockStart)
-
 	tests := map[string]testT{
 		"if certificate is not in Issuing state, then do nothing": {
 			certificate: exampleBundle.Certificate,
@@ -213,7 +213,38 @@ func TestIssuingController(t *testing.T) {
 			},
 			expectedErr: false,
 		},
-
+		"if certificate is in Issuing state, one CertificateRequest that has failed during previous issuance, do nothing": {
+			certificate: exampleBundle.Certificate,
+			builder: &testpkg.Builder{
+				CertManagerObjects: []runtime.Object{
+					gen.CertificateFrom(issuingCert),
+					gen.CertificateRequestFrom(exampleBundle.CertificateRequestFailed,
+						gen.AddCertificateRequestAnnotations(map[string]string{
+							cmapi.CertificateRequestRevisionAnnotationKey: "2", // Current Certificate revision=1
+						}),
+						gen.SetCertificateRequestStatusCondition(cmapi.CertificateRequestCondition{
+							Type:    cmapi.CertificateRequestConditionReady,
+							Status:  cmmeta.ConditionFalse,
+							Reason:  cmapi.CertificateRequestReasonFailed,
+							Message: "The certificate request failed because of reasons",
+						}),
+						gen.SetCertificateRequestFailureTime(metav1.Time{Time: metaFixedClockStart.Time.Add(time.Hour * -1)}),
+					)},
+				KubeObjects: []runtime.Object{
+					&corev1.Secret{
+						ObjectMeta: metav1.ObjectMeta{
+							Name:      nextPrivateKeySecretName,
+							Namespace: exampleBundle.Certificate.Namespace,
+						},
+						Data: map[string][]byte{
+							corev1.TLSPrivateKeyKey: exampleBundle.PrivateKeyBytes,
+						},
+					},
+				},
+				ExpectedActions: []testpkg.Action{},
+			},
+			expectedErr: false,
+		},
 		"if certificate is in Issuing state, one CertificateRequest, but has failed, set failed state and log event": {
 			certificate: exampleBundle.Certificate,
 			builder: &testpkg.Builder{