diff --git a/openhcl/underhill_attestation/src/jwt.rs b/openhcl/underhill_attestation/src/jwt.rs
index 4c51faa61c..8403c7e219 100644
--- a/openhcl/underhill_attestation/src/jwt.rs
+++ b/openhcl/underhill_attestation/src/jwt.rs
@@ -58,6 +58,8 @@ pub(crate) enum CertificateChainValidationError {
     VerifyChildSignatureWithParentPublicKey(#[source] crypto::x509::X509Error),
     #[error("cert chain validation failed -- signature mismatch")]
     CertChainSignatureMismatch,
+    #[error("failed to check if the certificate was issued by the issuer")]
+    CheckCertificateIssuedByIssuer(#[source] crypto::x509::X509Error),
     #[error("cert chain validation failed -- subject and issuer mismatch")]
     CertChainSubjectIssuerMismatch,
 }
@@ -251,7 +253,9 @@ fn validate_cert_chain(
                 Err(CertificateChainValidationError::CertChainSignatureMismatch)?
             }
 
-            let issued = parent.issued(child);
+            let issued = parent
+                .issued(child)
+                .map_err(CertificateChainValidationError::CheckCertificateIssuedByIssuer)?;
             if !issued {
                 Err(CertificateChainValidationError::CertChainSubjectIssuerMismatch)?
             }
diff --git a/support/crypto/src/x509/mod.rs b/support/crypto/src/x509/mod.rs
index 659f9b358a..524b417a99 100644
--- a/support/crypto/src/x509/mod.rs
+++ b/support/crypto/src/x509/mod.rs
@@ -44,7 +44,7 @@ impl X509Certificate {
     }
 
     /// Check if this certificate (acting as issuer) issued `subject`.
-    pub fn issued(&self, subject: &X509Certificate) -> bool {
+    pub fn issued(&self, subject: &X509Certificate) -> Result<bool, X509Error> {
         self.0.issued(&subject.0)
     }
 
diff --git a/support/crypto/src/x509/ossl.rs b/support/crypto/src/x509/ossl.rs
index 0d0d6b65e0..8bb672e280 100644
--- a/support/crypto/src/x509/ossl.rs
+++ b/support/crypto/src/x509/ossl.rs
@@ -33,9 +33,13 @@ impl X509CertificateInner {
             .map_err(|e| err(e, "verifying certificate signature"))
     }
 
-    pub fn issued(&self, subject: &X509CertificateInner) -> bool {
-        let result = self.0.issued(&subject.0);
-        result == openssl::x509::X509VerifyResult::OK
+    pub fn issued(&self, subject: &X509CertificateInner) -> Result<bool, X509Error> {
+        // `X509_check_issued` only performs deterministic comparisons on
+        // already-parsed data (name, AKID/SKID, serial, KeyUsage) and cannot
+        // fail with internal errors. Per the OpenSSL docs, every non-OK
+        // result is an `X509_V_ERR*` constant "indicating why the issuer
+        // does not match" — i.e., a legitimate `Ok(false)`.
+        Ok(self.0.issued(&subject.0) == openssl::x509::X509VerifyResult::OK)
     }
 
     pub fn to_der(&self) -> Result<Vec<u8>, X509Error> {
diff --git a/support/crypto/src/x509/symcrypt.rs b/support/crypto/src/x509/symcrypt.rs
index 79f73f1be0..74ef7096c7 100644
--- a/support/crypto/src/x509/symcrypt.rs
+++ b/support/crypto/src/x509/symcrypt.rs
@@ -72,8 +72,71 @@ impl X509CertificateInner {
         Ok(true)
     }
 
-    pub fn issued(&self, subject: &X509CertificateInner) -> bool {
-        self.0.tbs_certificate().subject() == subject.0.tbs_certificate().issuer()
+    pub fn issued(&self, subject: &X509CertificateInner) -> Result<bool, X509Error> {
+        use x509_cert::ext::pkix::AuthorityKeyIdentifier;
+        use x509_cert::ext::pkix::KeyUsage;
+        use x509_cert::ext::pkix::SubjectKeyIdentifier;
+        use x509_cert::ext::pkix::name::GeneralName;
+
+        let issuer_tbs = self.0.tbs_certificate();
+        let subject_tbs = subject.0.tbs_certificate();
+
+        // The subject's issuer name must match the issuer's subject name.
+        if subject_tbs.issuer() != issuer_tbs.subject() {
+            return Ok(false);
+        }
+
+        // If this certificate has a KeyUsage extension, it must permit
+        // signing other certificates.
+        let ku = issuer_tbs
+            .get_extension::<KeyUsage>()
+            .map_err(|e| der_err(e, "parsing KeyUsage extension"))?;
+        if let Some((_crit, ku)) = ku
+            && !ku.key_cert_sign()
+        {
+            return Ok(false);
+        }
+
+        // If the subject carries an AuthorityKeyIdentifier, validate its
+        // populated fields against this certificate (the candidate issuer).
+        let akid = subject_tbs
+            .get_extension::<AuthorityKeyIdentifier>()
+            .map_err(|e| der_err(e, "parsing AuthorityKeyIdentifier extension"))?;
+        if let Some((_crit, akid)) = akid {
+            if let Some(akid_key_id) = &akid.key_identifier {
+                let skid = issuer_tbs
+                    .get_extension::<SubjectKeyIdentifier>()
+                    .map_err(|e| der_err(e, "parsing SubjectKeyIdentifier extension"))?;
+                match skid {
+                    Some((_crit, ski)) => {
+                        if akid_key_id != &ski.0 {
+                            return Ok(false);
+                        }
+                    }
+                    None => return Ok(false),
+                }
+            }
+            if let Some(akid_serial) = &akid.authority_cert_serial_number {
+                if akid_serial != issuer_tbs.serial_number() {
+                    return Ok(false);
+                }
+            }
+            if let Some(gens) = &akid.authority_cert_issuer {
+                let mut has_dn = false;
+                let has_matching_dn = gens.iter().any(|g| match g {
+                    GeneralName::DirectoryName(dn) => {
+                        has_dn = true;
+                        dn == issuer_tbs.subject()
+                    }
+                    _ => false,
+                });
+                if has_dn && !has_matching_dn {
+                    return Ok(false);
+                }
+            }
+        }
+
+        Ok(true)
     }
 
     pub fn to_der(&self) -> Result<Vec<u8>, X509Error> {