diff --git a/internal/controller/certificates/policies/checks.go b/internal/controller/certificates/policies/checks.go
index 9e6f1224a97..4341c773c54 100644
--- a/internal/controller/certificates/policies/checks.go
+++ b/internal/controller/certificates/policies/checks.go
@@ -166,6 +166,35 @@ func SecretIssuerAnnotationsNotUpToDate(input Input) (string, string, bool) {
 	return "", "", false
 }
 
+// SecretPublicKeyDiffersFromCurrentCertificateRequest checks that the current CertificateRequest
+// contains a CSR that is signed by the key stored in the Secret. A failure is often caused by the
+// Secret being changed outside of the control of cert-manager, causing the current CertificateRequest
+// to no longer match what is stored in the Secret.
+func SecretPublicKeyDiffersFromCurrentCertificateRequest(input Input) (string, string, bool) {
+	if input.CurrentRevisionRequest == nil {
+		return "", "", false
+	}
+	pk, err := pki.DecodePrivateKeyBytes(input.Secret.Data[corev1.TLSPrivateKeyKey])
+	if err != nil {
+		return InvalidKeyPair, fmt.Sprintf("Issuing certificate as Secret contains invalid private key data: %v", err), true
+	}
+
+	csr, err := pki.DecodeX509CertificateRequestBytes(input.CurrentRevisionRequest.Spec.Request)
+	if err != nil {
+		return InvalidCertificateRequest, fmt.Sprintf("Failed to decode current CertificateRequest: %v", err), true
+	}
+
+	equal, err := pki.PublicKeysEqual(csr.PublicKey, pk.Public())
+	if err != nil {
+		return InvalidCertificateRequest, fmt.Sprintf("CertificateRequest's public key is invalid: %v", err), true
+	}
+	if !equal {
+		return SecretMismatch, "Secret contains a private key that does not match the current CertificateRequest", true
+	}
+
+	return "", "", false
+}
+
 func CurrentCertificateRequestNotValidForSpec(input Input) (string, string, bool) {
 	if input.CurrentRevisionRequest == nil {
 		// Fallback to comparing the Certificate spec with the issued certificate.
diff --git a/internal/controller/certificates/policies/checks_test.go b/internal/controller/certificates/policies/checks_test.go
index 381952cb21c..09aa477e95b 100644
--- a/internal/controller/certificates/policies/checks_test.go
+++ b/internal/controller/certificates/policies/checks_test.go
@@ -213,6 +213,31 @@ func Test_NewTriggerPolicyChain(t *testing.T) {
 			message: "Issuing certificate as Secret was previously issued by IssuerKind.new.example.com/testissuer",
 			reissue: true,
 		},
+		"trigger if the Secret contains a different private key than was used to sign the CSR": {
+			certificate: &cmapi.Certificate{Spec: cmapi.CertificateSpec{SecretName: "something"}},
+			secret: &corev1.Secret{ObjectMeta: metav1.ObjectMeta{Name: "something"},
+				Data: map[string][]byte{
+					corev1.TLSPrivateKeyKey: staticFixedPrivateKey,
+					corev1.TLSCertKey: testcrypto.MustCreateCert(
+						t, staticFixedPrivateKey,
+						&cmapi.Certificate{Spec: cmapi.CertificateSpec{CommonName: "example.com"}},
+					),
+				},
+			},
+			request: &cmapi.CertificateRequest{Spec: cmapi.CertificateRequestSpec{
+				IssuerRef: cmmeta.ObjectReference{
+					Name:  "testissuer",
+					Kind:  "IssuerKind",
+					Group: "group.example.com",
+				},
+				Request: testcrypto.MustGenerateCSRImpl(t, testcrypto.MustCreatePEMPrivateKey(t), &cmapi.Certificate{Spec: cmapi.CertificateSpec{
+					CommonName: "example.com",
+				}}),
+			}},
+			reason:  SecretMismatch,
+			message: "Secret contains a private key that does not match the current CertificateRequest",
+			reissue: true,
+		},
 		// we only have a basic test here for this as unit tests for the
 		// `pki.RequestMatchesSpec` function cover all other cases.
 		"trigger issuance when CertificateRequest does not match certificate spec": {
diff --git a/internal/controller/certificates/policies/constants.go b/internal/controller/certificates/policies/constants.go
index 6afde6e0e74..32d556fdd58 100644
--- a/internal/controller/certificates/policies/constants.go
+++ b/internal/controller/certificates/policies/constants.go
@@ -29,6 +29,10 @@ const (
 	// InvalidCertificate is a policy violation whereby the signed certificate in
 	// the Input Secret could not be parsed or decoded.
 	InvalidCertificate string = "InvalidCertificate"
+	// InvalidCertificateRequest is a policy violation whereby the CSR in
+	// the Input CertificateRequest could not be parsed or decoded.
+	InvalidCertificateRequest string = "InvalidCertificateRequest"
+
 	// SecretMismatch is a policy violation reason for a scenario where Secret's
 	// private key does not match spec.
 	SecretMismatch string = "SecretMismatch"
diff --git a/internal/controller/certificates/policies/policies.go b/internal/controller/certificates/policies/policies.go
index ff8f27cc56b..37dd60caa41 100644
--- a/internal/controller/certificates/policies/policies.go
+++ b/internal/controller/certificates/policies/policies.go
@@ -72,6 +72,7 @@ func NewTriggerPolicyChain(c clock.Clock) Chain {
 		SecretPublicKeysDiffer,
 		SecretPrivateKeyMatchesSpec,
 		SecretIssuerAnnotationsNotUpToDate,
+		SecretPublicKeyDiffersFromCurrentCertificateRequest,
 		CurrentCertificateRequestNotValidForSpec,
 		CurrentCertificateNearingExpiry(c),
 	}
@@ -84,6 +85,7 @@ func NewReadinessPolicyChain(c clock.Clock) Chain {
 		SecretDoesNotExist,
 		SecretIsMissingData,
 		SecretPublicKeysDiffer,
+		SecretPublicKeyDiffersFromCurrentCertificateRequest,
 		CurrentCertificateRequestNotValidForSpec,
 		CurrentCertificateHasExpired(c),
 	}
diff --git a/pkg/controller/certificates/readiness/readiness_controller_test.go b/pkg/controller/certificates/readiness/readiness_controller_test.go
index b4da05de563..1b44908ca0f 100644
--- a/pkg/controller/certificates/readiness/readiness_controller_test.go
+++ b/pkg/controller/certificates/readiness/readiness_controller_test.go
@@ -467,7 +467,11 @@ func TestNewReadinessPolicyChain(t *testing.T) {
 					Name:  "testissuer",
 					Kind:  "IssuerKind",
 					Group: "group.example.com",
-				})),
+				}),
+				gen.SetCertificateRequestCSR(testcrypto.MustGenerateCSRImpl(t, privKey,
+					gen.Certificate("something",
+						gen.SetCertificateCommonName("new.example.com")))),
+			),
 			reason:         policies.Expired,
 			message:        "Certificate expired on Sun, 31 Dec 0000 23:00:00 UTC",
 			violationFound: true,