rfc5280

rfc5280::aki::critical-aki

Produces the following invalid chain:

root -> EE

The root cert has an AKI extension marked as critical, which is disallowed under RFC 5280 4.2.1.1:

Conforming CAs MUST mark this extension as non-critical.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unhandled critical extension
rustls-webpki	✅	trusted certs: trust anchor extraction failed
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	✅	unhandled critical extension
rust-webpki	✅	trusted certs: trust anchor extraction failed
openssl-3.0.14	✅	unhandled critical extension
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	unhandled critical extension
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("Certificate extension has incorrect criticality"))
openssl-3.2.2	✅	unhandled critical extension

rfc5280::aki::leaf-missing-aki

Produces the following invalid chain:

root -> EE

The EE cert is signed by the root but missing the AKI extension, which is forbidden under RFC 5280 4.2.1.1.

The keyIdentifier field of the authorityKeyIdentifier extension MUST be included in all certificates generated by conforming CAs to facilitate certification path construction.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	Missing Authority Key Identifier
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	Missing Authority Key Identifier
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	Missing Authority Key Identifier
pyca-cryptography-42.0.8	✅	validation failed: Other("Certificate is missing required extension")
openssl-3.2.2	✅	Missing Authority Key Identifier

rfc5280::aki::intermediate-missing-aki

Produces the following invalid chain:

root -> intermediate -> EE

The intermediate is signed by the root but missing the AKI extension, which is forbidden under RFC 5280 4.2.1.1.

The keyIdentifier field of the authorityKeyIdentifier extension MUST be included in all certificates generated by conforming CAs to facilitate certification path construction.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	Missing Authority Key Identifier
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	Missing Authority Key Identifier
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	Missing Authority Key Identifier
pyca-cryptography-42.0.8	🚧	testcase skipped (explicitly unsupported case)
openssl-3.2.2	✅	Missing Authority Key Identifier

rfc5280::aki::self-signed-root-missing-aki

Produces the following valid chain:

root -> EE

The root cert is missing the AKI extension, which is ordinarily forbidden under RFC 5280 4.2.1.1 unless the certificate is self-signed, which this root is:

The keyIdentifier field of the authorityKeyIdentifier extension MUST be included in all certificates generated by conforming CAs to facilitate certification path construction. There is one exception; where a CA distributes its public key in the form of a "self-signed" certificate, the authority key identifier MAY be omitted.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	✅	N/A
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::aki::cross-signed-root-missing-aki

Produces the following invalid chain:

root -> EE

The root is cross signed by another root but missing the AKI extension, which is ambiguous but potentially disallowed under RFC 5280 4.2.1.1.

The keyIdentifier field of the authorityKeyIdentifier extension MUST be included in all certificates generated by conforming CAs to facilitate certification path construction.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	pedantic-rfc5280	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	🚧	testcase skipped (explicit unsupported feature)
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::eku::ee-wrong-eku

Produces the following invalid chain:

root -> EE

The chain is correctly constructed, but the EE cert contains an Extended Key Usage extension that contains just id-kp-clientAuth while the validator expects id-kp-serverAuth.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unsuitable certificate purpose
rustls-webpki	✅	RequiredEkuNotFound
gnutls-certtool-3.7.3	🚧	custom EKUs not yet supported
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unsupported certificate purpose
rust-webpki	✅	RequiredEkuNotFound
openssl-3.0.14	✅	unsuitable certificate purpose
certvalidator-0.11.1	✅	The X.509 certificate provided is not valid for securing TLS connections
openssl-3.1.6	✅	unsuitable certificate purpose
pyca-cryptography-42.0.8	✅	validation failed: Other("required EKU not found")
openssl-3.2.2	✅	unsuitable certificate purpose

rfc5280::eku::ee-without-eku

Produces the following valid chain:

root -> EE

The EE is missing an extKeyUsage extension, which is permitted under RFC 5280 4.2.1.12.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	webpki::eku::ee-without-eku	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	✅	N/A
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::nc::permitted-dns-mismatch

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted dNSName "example.com", whereas the leaf certificate has a SubjectAlternativeName with a dNSName of "not-example.com".

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	hostname mismatch
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	Hostname mismatch
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	hostname mismatch
certvalidator-0.11.1	✅	The X.509 certificate provided is not valid for example.com. Valid hostnames include: not-example.com
openssl-3.1.6	✅	hostname mismatch
pyca-cryptography-42.0.8	✅	validation failed: Other("leaf certificate has no matching subjectAltName")
openssl-3.2.2	✅	hostname mismatch

rfc5280::nc::excluded-dns-match

Produces the following invalid chain:

root -> ICA -> leaf

The ICA contains a NameConstraints extension with an excluded dNSName of "example.com", matching the leaf's SubjectAlternativeName.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	excluded subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	excluded subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	excluded subtree violation
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	✅	excluded subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("excluded name constraint matched SAN"))
openssl-3.2.2	✅	excluded subtree violation

rfc5280::nc::permitted-dns-match

Produces the following valid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted dNSName of "example.com", matching the leaf's SubjectAlternativeName.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::nc::permitted-dns-match-noncritical

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted dNSName of "example.com", matching the leaf's SubjectAlternativeName. However, the NameConstraints extension is not marked as critical, which is required by the RFC 5280 profile.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	rfc5280-incompatible-with-webpki	undetermined	webpki::nc::permitted-dns-match-noncritical	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	🚧	testcase skipped (explicit unsupported feature)
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::nc::permitted-dns-match-more

Produces the following valid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted dNSName of "example.com". The leaf's "foo.bar.example.com" satisfies this constraint per the RFC 5280 profile:

DNS name restrictions are expressed as host.example.com. Any DNS name that can be constructed by simply adding zero or more labels to the left-hand side of the name satisfies the name constraint. For example, www.host.example.com would satisfy the constraint but host1.example.com would not.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::nc::excluded-dns-match-second

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with an excluded dNSName of "not-allowed.example.com". This should match the leaf's second SubjectAlternativeName entry.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	excluded subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	excluded subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	excluded subtree violation
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	excluded subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("excluded name constraint matched SAN"))
openssl-3.2.2	✅	excluded subtree violation

rfc5280::nc::permitted-ip-mismatch

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted iPAddress of 192.0.2.0/24, which does not match the iPAddress in the SubjectAlternativeName of the leaf.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	permitted subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	permitted subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	permitted subtree violation
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	permitted subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("no permitted name constraints matched SAN"))
openssl-3.2.2	✅	permitted subtree violation

rfc5280::nc::excluded-ipv4-match

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with an excluded iPAddress of 192.0.2.0/24, matching the iPAddress in the SubjectAlternativeName of the leaf.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	excluded subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	excluded subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	excluded subtree violation
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	excluded subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("excluded name constraint matched SAN"))
openssl-3.2.2	✅	excluded subtree violation

rfc5280::nc::excluded-ipv6-match

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with an excluded iPAddress of ::1/128, matching the iPAddress in the SubjectAlternativeName of the leaf.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	excluded subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	excluded subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	excluded subtree violation
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	excluded subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("excluded name constraint matched SAN"))
openssl-3.2.2	✅	excluded subtree violation

rfc5280::nc::permitted-ipv4-match

Produces the following valid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted iPAddress of 192.0.2.0/24, which matches the iPAddress in the SubjectAlternativeName of the leaf.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::nc::permitted-ipv6-match

Produces the following valid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted iPAddress of ::1/128, which matches the iPAddress in the SubjectAlternativeName of the leaf.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::nc::permitted-dn-mismatch

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted DirectoryName of CN=foo. This should not match the child's DirectoryName of CN=not-foo.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	name-constraint-dn	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	hostname mismatch
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	Hostname mismatch
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	hostname mismatch
certvalidator-0.11.1	✅	The X.509 certificate provided is not valid for example.com. Valid hostnames include:
openssl-3.1.6	✅	hostname mismatch
pyca-cryptography-42.0.8	🚧	testcase skipped (explicit unsupported feature)
openssl-3.2.2	✅	hostname mismatch

rfc5280::nc::excluded-dn-match

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with an excluded DirectoryName of CN=foo, matching the leaf's SubjectAlternativeName.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	name-constraint-dn	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	hostname mismatch
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	Hostname mismatch
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	hostname mismatch
certvalidator-0.11.1	✅	The X.509 certificate provided is not valid for example.com. Valid hostnames include:
openssl-3.1.6	✅	hostname mismatch
pyca-cryptography-42.0.8	🚧	testcase skipped (explicit unsupported feature)
openssl-3.2.2	✅	hostname mismatch

rfc5280::nc::permitted-dn-match

Produces the following valid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted DirectoryName of CN=foo, matching the leaf's SubjectAlternativeName.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	name-constraint-dn	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	❌ (unexpected failure)	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected failure)	validation: x509: unhandled critical extension
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	❌ (unexpected failure)	'NoneType' object has no attribute 'value'
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	🚧	testcase skipped (explicit unsupported feature)
openssl-3.2.2	✅	N/A

rfc5280::nc::permitted-dn-match-subject-san-mismatch

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted DirectoryName of "CN=foo", matching the leaf's SubjectAlternativeName but not its subject. The leaf must be rejected per RFC 5280 4.2.1.10 due to this mismatch:

Restrictions of the form directoryName MUST be applied to the subject field in the certificate (when the certificate includes a non-empty subject field) and to any names of type directoryName in the subjectAltName extension.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	name-constraint-dn	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	hostname mismatch
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	Hostname mismatch
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	hostname mismatch
certvalidator-0.11.1	✅	The X.509 certificate provided is not valid for example.com. Valid hostnames include:
openssl-3.1.6	✅	hostname mismatch
pyca-cryptography-42.0.8	🚧	testcase skipped (explicit unsupported feature)
openssl-3.2.2	✅	hostname mismatch

rfc5280::nc::excluded-dn-match-sub-mismatch

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with an excluded DirectoryName of "CN=foo", matching the leaf's subject but not its SubjectAlternativeName. The leaf must be rejected per RFC 5280 4.2.1.10 due to this match:

Restrictions of the form directoryName MUST be applied to the subject field in the certificate (when the certificate includes a non-empty subject field) and to any names of type directoryName in the subjectAltName extension.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	name-constraint-dn	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	hostname mismatch
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	Hostname mismatch
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	hostname mismatch
certvalidator-0.11.1	✅	The X.509 certificate provided is not valid for example.com. Valid hostnames include:
openssl-3.1.6	✅	hostname mismatch
pyca-cryptography-42.0.8	🚧	testcase skipped (explicit unsupported feature)
openssl-3.2.2	✅	hostname mismatch

rfc5280::nc::permitted-self-issued

Produces the following valid chain:

root -> intermediate -> leaf

The root contains a NameConstraints extension with a permitted dNSName of "example.com", whereas the intermediate certificate has a SubjectAlternativeName with a dNSName of "not-example.com".

Normally, this would mean that the chain would be rejected, however the intermediate is self-issued so name constraints don't apply to it.

Name constraints are not applied to self-issued certificates (unless the certificate is the final certificate in the path). (This could prevent CAs that use name constraints from employing self-issued certificates to implement key rollover.)

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	❌ (unexpected failure)	InvalidSignatureForPublicKey
gnutls-certtool-3.7.3	❌ (unexpected failure)	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	❌ (unexpected failure)	validation: x509: a root or intermediate certificate is not authorized to sign for this name: DNS name "not-example.com" is not permitted by any constraint
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::nc::excluded-self-issued-leaf

Produces the following invalid chain:

root -> intermediate -> leaf

The root contains a NameConstraints extension with a permitted dNSName of "example.com", whereas the leaf certificate has a SubjectAlternativeName with a dNSName of "not-example.com".

In this case, the chain would still be rejected as name constraints do apply to self-issued certificates if they are in the leaf position.

Name constraints are not applied to self-issued certificates (unless the certificate is the final certificate in the path). (This could prevent CAs that use name constraints from employing self-issued certificates to implement key rollover.)

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	permitted subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	permitted subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	permitted subtree violation
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	permitted subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("no permitted name constraints matched SAN"))
openssl-3.2.2	✅	permitted subtree violation

rfc5280::nc::excluded-match-permitted-and-excluded

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted and excluded dNSName of "example.com", both of which match the leaf's SubjectAlternativeName.

The excluded constraint takes precedence over the the permitted so this chain should be marked as invalid.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	excluded subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	excluded subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	excluded subtree violation
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	excluded subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("excluded name constraint matched SAN"))
openssl-3.2.2	✅	excluded subtree violation

rfc5280::nc::permitted-different-constraint-type

Produces the following valid chain:

root -> leaf

The root contains a NameConstraints extension with a permitted iPAddress of 192.0.2.0/24, while the leaf's SubjectAlternativeName is a dNSName.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::nc::excluded-different-constraint-type

Produces the following valid chain:

root -> leaf

The root contains a NameConstraints extension with an excluded iPAddress of 192.0.2.0/24, while the leaf's SubjectAlternativeName is a dNSName.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::nc::invalid-dnsname-wildcard

Produces the following invalid chain:

root -> leaf

The root contains a Name Constraints extension with a malformed dNSName (uses a wildcard pattern, which is not permitted under RFC 5280).

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	permitted subtree violation
rustls-webpki	✅	MalformedNameConstraint
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	permitted subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	permitted subtree violation
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	permitted subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("malformed DNS name constraint: *.example.com"))
openssl-3.2.2	✅	permitted subtree violation

rfc5280::nc::invalid-dnsname-leading-period

Produces the following invalid chain:

root -> leaf

The root contains a Name Constraint extension with a malformed DNS name (uses a leading period, which is not permitted under RFC 5280 4.2.1.10).

This is widely (incorrectly) accepted by implementations due to OpenSSL accepting it and due to misreadings of RFC 5280, which allows a leading period in URI constraints but not DNS constraints.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("malformed DNS name constraint: .example.com"))
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::nc::invalid-ipv4-address

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a malformed IPv4 iPAddress (not in CIDR form).

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unsupported or invalid name syntax
rustls-webpki	✅	InvalidNetworkMaskConstraint
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unsupported or invalid name syntax
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	unsupported or invalid name syntax
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	unsupported or invalid name syntax
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("malformed IP name constraints: [127, 0, 0, 1]"))
openssl-3.2.2	✅	unsupported or invalid name syntax

rfc5280::nc::invalid-ipv6-address

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a malformed IPv6 iPAddress (not in CIDR form).

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unsupported or invalid name syntax
rustls-webpki	✅	InvalidNetworkMaskConstraint
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unsupported or invalid name syntax
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	unsupported or invalid name syntax
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	unsupported or invalid name syntax
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("malformed IP name constraints: [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1]"))
openssl-3.2.2	✅	unsupported or invalid name syntax

rfc5280::nc::invalid-email-address

Produces the following invalid chain:

root -> leaf

The root contains a NameConstraints extension with a malformed RFC822 name constraint (invalid@invalid@example.com, which is not a valid email address).

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	CLIENT	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	🚧	non-SERVER testcases not supported yet
rustls-webpki	🚧	non-SERVER testcases not supported yet
gnutls-certtool-3.7.3	🚧	non-SERVER testcases not yet supported
gocryptox509-go1.22.5	🚧	unimplemented validationKindClient
openssl-1.1	🚧	non-SERVER testcases not supported yet
rust-webpki	🚧	non-SERVER testcases not supported yet
openssl-3.0.14	🚧	non-SERVER testcases not supported yet
certvalidator-0.11.1	🚧	non-SERVER cases not supported yet
openssl-3.1.6	🚧	non-SERVER testcases not supported yet
pyca-cryptography-42.0.8	🚧	non-SERVER cases not supported yet
openssl-3.2.2	🚧	non-SERVER testcases not supported yet

rfc5280::nc::not-allowed-in-ee-noncritical

Produces the following invalid chain:

root -> EE

The EE contains a non-critical NameConstraints extension, which is not permitted under the RFC 5280 profile:

The name constraints extension, which MUST be used only in a CA certificate

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	✅	validation failed: Other("Certificate contains prohibited extension")
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::nc::not-allowed-in-ee-critical

Produces the following invalid chain:

root -> EE

The EE contains a critical NameConstraints extension, which is not permitted under the RFC 5280 profile:

The name constraints extension, which MUST be used only in a CA certificate

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	✅	The path could not be validated because the end-entity certificate contains the following unsupported critical extension: name_constraints
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	✅	validation failed: Other("Certificate contains prohibited extension")
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::nc::intermediate-with-san-rejected-by-intermediate-nc

Produces the following invalid chain:

root -> ICA1 -> ICA2 -> EE
         |       |       |
         |       |       |
         NC     SAN1    SAN2

ICA1 contains a NameConstraints extension that forbids SAN1 (forbidden.example.com) and permits SAN2 (permitted.example.com), which should be rejected under RFC 5280:

The name constraints extension, which MUST be used only in a CA certificate, indicates a name space within which all subject names in subsequent certificates in a certification path MUST be located.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	permitted subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	permitted subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	permitted subtree violation
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	✅	permitted subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("no permitted name constraints matched SAN"))
openssl-3.2.2	✅	permitted subtree violation

rfc5280::nc::intermediate-with-san-rejected-by-root-nc

Produces the following invalid chain:

root -> ICA1 -> ICA2 -> EE
 |               |       |
 |               |       |
 NC             SAN1    SAN2

The root contains a NameConstraints extension that forbids SAN1 (forbidden.example.com) and permits SAN2 (permitted.example.com), which should be rejected under RFC 5280:

The name constraints extension, which MUST be used only in a CA certificate, indicates a name space within which all subject names in subsequent certificates in a certification path MUST be located.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	permitted subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	permitted subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	permitted subtree violation
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	permitted subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("no permitted name constraints matched SAN"))
openssl-3.2.2	✅	permitted subtree violation

rfc5280::nc::restrictive-permits-in-intermediates-narrows

Produces the following invalid chain:

root     ->     ICA1     ->     ICA2     ->     EE
                 |               |               |
              permits:        permits:       SAN: foo.example.com
          foo.example.com   bar.example.com
          bar.example.com

ICA1 contains a NameConstraints extension permitting foo.example.com and bar.example.com, while ICA2 contains a NameConstraints extension permitting only bar.example.com. The EE then contains a SAN for foo.example.com, which should be rejected under RFC 5280:

a name space within which all subject names in subsequent certificates in a certification path MUST be located.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	permitted subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	permitted subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	permitted subtree violation
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	✅	permitted subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("no permitted name constraints matched SAN"))
openssl-3.2.2	✅	permitted subtree violation

rfc5280::nc::restrictive-permits-in-intermediates-widens

Produces the following invalid chain:

root     ->     ICA1     ->     ICA2     ->     EE
                 |               |               |
              permits:        permits:       SAN: foo.example.com
          bar.example.com   foo.example.com
                            bar.example.com

ICA1 contains a NameConstraints extension permitting only bar.example.com, while ICA2 contains a NameConstraints extension permitting foo.example.com and bar.example.com. The EE then contains a SAN for foo.example.com, which should be rejected under RFC 5280:

a name space within which all subject names in subsequent certificates in a certification path MUST be located.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	permitted subtree violation
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	permitted subtree violation
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	permitted subtree violation
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	✅	permitted subtree violation
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("no permitted name constraints matched SAN"))
openssl-3.2.2	✅	permitted subtree violation

rfc5280::nc::nc-permits-invalid-dns-san

Produces the following invalid chain:

root -> ICA (NC: example.com) -> EE (SAN: .example.com)

The ICA contains a NC that allows example.com and all subdomains, but the EE's SAN contains a malformed DNS name (.example.com). This should fail per RFC 5280, since all names MUST be located within the permitted namespace.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	✅	MalformedDnsIdentifier
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("unsatisfiable DNS name constraint: malformed SAN .example.com"))
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::nc::nc-permits-invalid-ip-san

Produces the following invalid chain:

root -> ICA (NC: 192.0.2.0/24) -> EE (SAN: 192.0.2.0/24)

The ICA contains a NC that permits 192.0.2.0/24, but the EE's SAN is malformed (containing a CIDR range instead of an IP address). This should fail per RFC 5280, since all names MUST be located within the permitted namespace.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unsupported or invalid name syntax
rustls-webpki	✅	BadDer
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unsupported or invalid name syntax
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	unsupported or invalid name syntax
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	✅	unsupported or invalid name syntax
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("unsatisfiable IP name constraint: malformed SAN [192, 0, 2, 0, 255, 255, 255, 0]"))
openssl-3.2.2	✅	unsupported or invalid name syntax

rfc5280::nc::nc-permits-invalid-email-san

Produces the following invalid chain:

root -> ICA (NC: example.com) -> EE (SAN: invalid@address@example.com)

The ICA contains a NC that permits any email inbox on example.com, but the EE's SAN is malformed (containing a malformed email address). This should fail per RFC 5280, since all names MUST be located within the permitted namespace.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	CLIENT	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	🚧	non-SERVER testcases not supported yet
rustls-webpki	🚧	non-SERVER testcases not supported yet
gnutls-certtool-3.7.3	🚧	non-SERVER testcases not yet supported
gocryptox509-go1.22.5	🚧	unimplemented validationKindClient
openssl-1.1	🚧	non-SERVER testcases not supported yet
rust-webpki	🚧	non-SERVER testcases not supported yet
openssl-3.0.14	🚧	non-SERVER testcases not supported yet
certvalidator-0.11.1	🚧	non-SERVER cases not supported yet
openssl-3.1.6	🚧	non-SERVER testcases not supported yet
pyca-cryptography-42.0.8	🚧	non-SERVER cases not supported yet
openssl-3.2.2	🚧	non-SERVER testcases not supported yet

rfc5280::nc::nc-forbids-alternate-chain-ica

Produces the following valid graph:

EE (SAN:X) +-> ICA_B' (SAN:Y) -> No root to chain to
           |-> ICA_B'' (no SAN) -> ICA_A (NC forbids SAN:Y) -> Root

ICA_B' and ICA_B'' are certificates for the same logical intermediate, but issued by different logical root CAs.

This graph allows validation through EE -> ICA_B'' -> Root.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected failure)	unable to get local issuer certificate
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	❌ (unexpected failure)	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	❌ (unexpected failure)	unable to get local issuer certificate
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	❌ (unexpected failure)	unable to get local issuer certificate
certvalidator-0.11.1	❌ (unexpected failure)	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	❌ (unexpected failure)	unable to get local issuer certificate
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	❌ (unexpected failure)	unable to get local issuer certificate

rfc5280::nc::nc-forbids-same-chain-ica

Produces the following valid graph:

EE (SAN:X) +-> ICA_B' (SAN:Y) -> ICA_A (forbid: SAN:Y) -> RCA_A
           |-> ICA_B'' (SAN:Z) -> RCA_B (no NC)

ICA_B' and ICA_B'' are certificates for the same logical intermediate, but chained to different logical root CAs. Both root CAs are trusted, but ICA_B' is issued through ICA_A, which forbids ICA_B''s SAN.

This graph allows validation through EE -> ICA_B'' -> RCA_B

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected failure)	excluded subtree violation
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	❌ (unexpected failure)	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	❌ (unexpected failure)	excluded subtree violation
rust-webpki	✅	N/A
openssl-3.0.14	❌ (unexpected failure)	excluded subtree violation
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	❌ (unexpected failure)	excluded subtree violation
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	❌ (unexpected failure)	excluded subtree violation

rfc5280::nc::nc-permits-email-exact

Produces the following valid graph:

root -> ICA (permit: foo@example.com) -> EE (SAN: foo@example.com)

Per RFC 5280 4.2.1.10 an email name constraint may specify a particular mailbox, like in this graph.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	CLIENT	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	🚧	non-SERVER testcases not supported yet
rustls-webpki	🚧	non-SERVER testcases not supported yet
gnutls-certtool-3.7.3	🚧	non-SERVER testcases not yet supported
gocryptox509-go1.22.5	🚧	unimplemented validationKindClient
openssl-1.1	🚧	non-SERVER testcases not supported yet
rust-webpki	🚧	non-SERVER testcases not supported yet
openssl-3.0.14	🚧	non-SERVER testcases not supported yet
certvalidator-0.11.1	🚧	non-SERVER cases not supported yet
openssl-3.1.6	🚧	non-SERVER testcases not supported yet
pyca-cryptography-42.0.8	🚧	non-SERVER cases not supported yet
openssl-3.2.2	🚧	non-SERVER testcases not supported yet

rfc5280::nc::nc-permits-email-domain

Produces the following valid graph:

root -> ICA (permit: example.com) -> EE (SAN: foo@example.com)

Per RFC 5280 4.2.1.10 an email name constraint may specify a host name to constrain all inboxes on that host.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	CLIENT	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	🚧	non-SERVER testcases not supported yet
rustls-webpki	🚧	non-SERVER testcases not supported yet
gnutls-certtool-3.7.3	🚧	non-SERVER testcases not yet supported
gocryptox509-go1.22.5	🚧	unimplemented validationKindClient
openssl-1.1	🚧	non-SERVER testcases not supported yet
rust-webpki	🚧	non-SERVER testcases not supported yet
openssl-3.0.14	🚧	non-SERVER testcases not supported yet
certvalidator-0.11.1	🚧	non-SERVER cases not supported yet
openssl-3.1.6	🚧	non-SERVER testcases not supported yet
pyca-cryptography-42.0.8	🚧	non-SERVER cases not supported yet
openssl-3.2.2	🚧	non-SERVER testcases not supported yet

rfc5280::nc::nc-forbids-othername

Produces the following invalid graph:

root -> ICA (forbid: ON) -> EE (SAN: ON)

RFC 5280 does not specify the handling other OtherName constraints, but does specify that implementations must either process (and therefore recognize) all constraints or outright reject the certificate.

If a name constraints extension that is marked as critical imposes constraints on a particular name form, and an instance of that name form appears in the subject field or subjectAltName extension of a subsequent certificate, then the application MUST either process the constraint or reject the certificate.

This testcase contains an ICA with a private OtherName (meaning the implementation will not recognize it), and therefore must reject the chain.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unsupported name constraint type
rustls-webpki	✅	NameConstraintViolation
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unsupported name constraint type
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	unsupported name constraint type
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	✅	unsupported name constraint type
pyca-cryptography-42.0.8	❌ (unexpected success)	N/A
openssl-3.2.2	✅	unsupported name constraint type

rfc5280::nc::nc-forbids-othername-noop

Produces the following valid graph:

root -> ICA (forbid: ON) -> EE (SAN: no ON)

RFC 5280 does not specify the handling other OtherName constraints, but does specify that implementations are only required to evaluate constraints for names that actually appear on the validation path.

In this case, ICA contains an OtherName Name Constraint but no actual SANs on the path contain any OtherName subjects, making the chain valid.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	❌ (unexpected failure)	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	❌ (unexpected failure)	validation: x509: unhandled critical extension
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	UnknownIssuer
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	❌ (unexpected failure)	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: name_constraints
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::pc::ica-noncritical-pc

Produces the following invalid chain:

root -> ICA -> EE

The ICA has a PolicyConstraints extension marked as non-critical, which is disallowed under RFC 5280 4.2.1.11:

Conforming CAs MUST mark this extension as critical.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	has-policy-constraints	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	🚧	testcase skipped (explicit unsupported feature)
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::san::malformed

Produces the following invalid chain:

root -> EE

The EE cert has a SubjectAlternativeName with a value in ASCII bytes, rather than in the expected DER encoding.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unable to get local issuer certificate
rustls-webpki	✅	leaf cert: X.509 parse failed
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unable to get local issuer certificate
rust-webpki	✅	leaf cert: X.509 parse failed
openssl-3.0.14	✅	unable to get local issuer certificate
certvalidator-0.11.1	✅	Insufficient data - 120 bytes requested but only 9 available while parsing asn1crypto.core.ParsableOctetString while parsing asn1crypto.x509.Extension
openssl-3.1.6	✅	unable to get local issuer certificate
pyca-cryptography-42.0.8	✅	validation failed: Malformed(ParseError { kind: ShortData })
openssl-3.2.2	✅	unable to get local issuer certificate

rfc5280::san::noncritical-with-empty-subject

Produces an invalid chain due to an invalid EE cert.

The EE cert contains a non-critical Subject Alternative Name extension, which is disallowed when the cert's Subject is empty under RFC 5280:

If the subject field contains an empty sequence, then the issuing CA MUST include a subjectAltName extension that is marked as critical.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	Subject empty and Subject Alt Name extension not critical
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	Subject empty and Subject Alt Name extension not critical
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	Subject empty and Subject Alt Name extension not critical
pyca-cryptography-42.0.8	✅	validation failed: Other("EE subjectAltName MUST be critical when subject is empty")
openssl-3.2.2	✅	Subject empty and Subject Alt Name extension not critical

rfc5280::san::underscore-dns

Produces an invalid chain due to an invalid EE cert.

The EE cert contains a Subject Alternative Name extension that contains an underscore, which is disallowed under RFC 5280 4.2.1.6:

When the subjectAltName extension contains a domain name system label, the domain name MUST be stored in the dNSName (an IA5String). The name MUST be in the "preferred name syntax", as specified by Section 3.5 of RFC 1034 and as modified by Section 2.1 of RFC 1123.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	✅	invalid domain name
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::serial::too-long

Produces an invalid chain due to an invalid EE cert.

The EE cert contains a serial number longer than 20 octets, which is disallowed under RFC 5280.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	pedantic-serial-number	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	✅	leaf cert: X.509 parse failed
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	✅	validation failed: Other("certificate must have a serial between 1 and 20 octets")
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::serial::zero

Produces an invalid chain due to an invalid EE cert.

The EE cert contains a serial number of zero, which is disallowed under RFC 5280.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	pedantic-serial-number	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	✅	leaf cert: X.509 parse failed
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	🚧	testcase skipped (explicitly unsupported case)
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::serial::negative

Produces an invalid chain due to an invalid EE cert. Verifies against a saved copy of a certificate with a negative serial number from the cryptography.io test suite since the API won't allow us to create certificates with negative serial numbers.

The EE cert contains a negative serial number, which is disallowed under RFC 5280.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	2016-09-01T00:00:00+00:00	pedantic-serial-number	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected success)	N/A
rustls-webpki	✅	CaUsedAsEndEntity
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	✅	leaf cert: X.509 parse failed
openssl-3.0.14	❌ (unexpected success)	N/A
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	❌ (unexpected success)	N/A
pyca-cryptography-42.0.8	✅	validation failed: Other("certificate serial number cannot be negative")
openssl-3.2.2	❌ (unexpected success)	N/A

rfc5280::ski::critical-ski

Produces the following invalid chain:

root -> EE

The root cert has an SKI extension marked as critical, which is disallowed under RFC 5280 4.2.1.2.

Conforming CAs MUST mark this extension as non-critical.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unable to get local issuer certificate
rustls-webpki	✅	trusted certs: trust anchor extraction failed
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate issuer is unknown.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	✅	unable to get local issuer certificate
rust-webpki	✅	trusted certs: trust anchor extraction failed
openssl-3.0.14	✅	unable to get local issuer certificate
certvalidator-0.11.1	✅	Unable to build a validation path for the certificate "Common Name: example.com" - no issuer matching "Common Name: x509-limbo-root" was found
openssl-3.1.6	✅	unable to get local issuer certificate
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("Certificate extension has incorrect criticality"))
openssl-3.2.2	✅	unable to get local issuer certificate

rfc5280::ski::root-missing-ski

Produces the following invalid chain:

root -> EE

The root cert is missing the SKI extension, which is disallowed under RFC 5280 4.2.1.2.

To facilitate certification path construction, this extension MUST appear in all conforming CA certificates, that is, all certificates including the basic constraints extension (Section 4.2.1.9) where the value of cA is TRUE.

Note: for roots, the SKI should be the same value as the AKI, therefore, this extension isn't strictly necessary, although required by the RFC.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	Missing Subject Key Identifier
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	Missing Subject Key Identifier
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	Missing Subject Key Identifier
pyca-cryptography-42.0.8	🚧	testcase skipped (explicitly unsupported case)
openssl-3.2.2	✅	Missing Subject Key Identifier

rfc5280::ski::intermediate-missing-ski

Produces the following invalid chain:

root -> ICA -> EE

The intermediate cert is missing the SKI extension, which is disallowed under RFC 5280 4.2.1.2.

To facilitate certification path construction, this extension MUST appear in all conforming CA certificates, that is, all certificates including the basic constraints extension (Section 4.2.1.9) where the value of cA is TRUE.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	Missing Subject Key Identifier
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	Missing Subject Key Identifier
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	Missing Subject Key Identifier
pyca-cryptography-42.0.8	🚧	testcase skipped (explicitly unsupported case)
openssl-3.2.2	✅	Missing Subject Key Identifier

rfc5280::validity::expired-root

Produces the following invalid chain:

root -> intermediate -> EE

All three certificates are well-formed, but the root (and only the root) is expired at the validation time.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	2022-01-01T00:00:00+00:00	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	certificate has expired
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	certificate has expired
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	certificate has expired
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	certificate has expired
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("cert is not valid at validation time"))
openssl-3.2.2	✅	certificate has expired

rfc5280::validity::expired-intermediate

Produces the following invalid chain:

root -> intermediate -> EE

All three certificates are well-formed, but the intermediate (and only the intermediate) is expired at the validation time.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	2022-01-01T00:00:00+00:00	N/A	critical	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	certificate has expired
rustls-webpki	✅	CertExpired
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	certificate has expired
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	certificate has expired
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 expired 2020-01-01 00:00:00Z
openssl-3.1.6	✅	certificate has expired
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("cert is not valid at validation time"))
openssl-3.2.2	✅	certificate has expired

rfc5280::validity::expired-leaf

Produces the following invalid chain:

root -> intermediate -> EE

All three certificates are well-formed, but the leaf (and only the leaf) is expired at the validation time.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	2022-01-01T00:00:00+00:00	N/A	critical	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	certificate has expired
rustls-webpki	✅	CertExpired
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	certificate has expired
rust-webpki	✅	CertExpired
openssl-3.0.14	✅	certificate has expired
certvalidator-0.11.1	✅	The path could not be validated because the end-entity certificate expired 2021-01-01 00:00:00Z
openssl-3.1.6	✅	certificate has expired
pyca-cryptography-42.0.8	✅	validation failed: Other("cert is not valid at validation time")
openssl-3.2.2	✅	certificate has expired

rfc5280::validity::notbefore-exact

Produces the following valid chain:

root -> ICA -> EE

EE becomes valid at 2024-03-01T00:00:00Z, and the chain is validated at exactly 2024-03-01T00:00:00Z.

RFC 5280 4.1.2.5 says that notBefore is inclusive, so this chain should validate:

The validity period for a certificate is the period of time from notBefore through notAfter, inclusive.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	2024-03-01T00:00:00+00:00	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	❌ (unexpected failure)	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	✅	N/A
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::validity::notbefore-fractional

Produces the following invalid chain:

root -> ICA -> EE

EE becomes valid at 2024-03-01T00:00:01Z, and the chain is validated at exactly 2024-03-01T00:00:00.999Z.

This is the counterpart to rfc5280::validity::notafter-fractional: despite rounding to the notBefore date, implementations should floor the validation time instead and subsequently reject this chain.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	2024-03-01T00:00:00.999000+00:00	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	certificate is not yet valid
rustls-webpki	✅	CertNotValidYet
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	certificate is not yet valid
rust-webpki	✅	CertNotValidYet
openssl-3.0.14	✅	certificate is not yet valid
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 is not valid until 2024-03-01 00:00:01Z
openssl-3.1.6	✅	certificate is not yet valid
pyca-cryptography-42.0.8	✅	validation failed: Other("cert is not valid at validation time")
openssl-3.2.2	✅	certificate is not yet valid

rfc5280::validity::notafter-exact

Produces the following valid chain:

root -> ICA -> EE

EE expires at 2024-04-01T00:00:00Z, and the chain is validated at exactly 2024-04-01T00:00:00Z.

RFC 5280 4.1.2.5 says that notAfter is inclusive, so this chain should validate:

The validity period for a certificate is the period of time from notBefore through notAfter, inclusive.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	2024-04-01T00:00:00+00:00	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected failure)	certificate has expired
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	❌ (unexpected failure)	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	❌ (unexpected failure)	certificate has expired
rust-webpki	✅	N/A
openssl-3.0.14	❌ (unexpected failure)	certificate has expired
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	❌ (unexpected failure)	certificate has expired
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	❌ (unexpected failure)	certificate has expired

rfc5280::validity::notafter-fractional

Produces the following ambiguous chain:

root -> ICA -> EE

EE expires at 2024-04-01T00:00:00Z, and the chain is validated at 2024-04-01T00:00:00.005Z, i.e. 5 milliseconds after the notAfter date.

RFC 5280 only allows second granularities in the validity interval, with two conflicting interpretations of how to handle the validity check:

1. Comparisons are performed at the granularity of the encoded representation, i.e. floor(time). Under this interpretation, the chain is valid, since the entire millisecond interval [0, .999...] is truncated to 0.
2. Comparisons are instantaneous. Under this interpretation the chain is invalid, since 5 milliseconds after the notAfter is factually after the notAfter.

There is no clear "winning" interpretation here, although CAs in the Web PKI have filed and handled compliance reports based on interpretation (1).

See also:

• https://bugzilla.mozilla.org/show_bug.cgi?id=1715455
• https://groups.google.com/a/mozilla.org/g/dev-security-policy/c/-BogZx_IJyk/m/gHm3l613AgAJ

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	2024-04-01T00:00:00.005000+00:00	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	❌ (unexpected failure)	certificate has expired
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	❌ (unexpected failure)	N/A
gocryptox509-go1.22.5	❌ (unexpected failure)	validation: x509: certificate has expired or is not yet valid: current time 2024-04-01T00:00:00Z is after 2024-04-01T00:00:00Z
openssl-1.1	❌ (unexpected failure)	certificate has expired
rust-webpki	✅	N/A
openssl-3.0.14	❌ (unexpected failure)	certificate has expired
certvalidator-0.11.1	❌ (unexpected failure)	The path could not be validated because intermediate certificate 1 expired 2024-04-01 00:00:00Z
openssl-3.1.6	❌ (unexpected failure)	certificate has expired
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	❌ (unexpected failure)	certificate has expired

rfc5280::ee-empty-issuer

Produces the following invalid chain:

root -> EE

This chain is invalid solely because of the EE cert's construction: it has an empty issuer name, which isn't allowed under the RFC 5280 profile.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unable to get local issuer certificate
rustls-webpki	✅	UnknownIssuer
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unable to get local issuer certificate
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	unable to get local issuer certificate
certvalidator-0.11.1	✅	Unable to build a validation path for the certificate "Common Name: empty-issuer" - no issuer matching "" was found
openssl-3.1.6	✅	unable to get local issuer certificate
pyca-cryptography-42.0.8	✅	validation failed: Other("certificate must have a non-empty Issuer")
openssl-3.2.2	✅	unable to get local issuer certificate

rfc5280::ca-empty-subject

Produces an invalid chain due to an invalid CA cert.

The CA cert contains an empty Subject SEQUENCE, which is disallowed under RFC 5280:

If the subject is a CA [...], then the subject field MUST be populated with a non-empty distinguished name

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	Issuer name empty
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	Issuer name empty
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	Issuer name empty
pyca-cryptography-42.0.8	✅	validation failed: Other("certificate must have a non-empty Issuer")
openssl-3.2.2	✅	Issuer name empty

rfc5280::unknown-critical-extension-ee

Produces the following invalid chain:

root -> EE

The EE cert has an extension, 1.3.6.1.4.1.55738.666.1, that no implementation should recognize. As this unrecognized extension is marked as critical, a chain should not be built with this EE.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unhandled critical extension
rustls-webpki	✅	leaf cert: X.509 parse failed
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate contains an unknown critical extension.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unhandled critical extension
rust-webpki	✅	leaf cert: X.509 parse failed
openssl-3.0.14	✅	unhandled critical extension
certvalidator-0.11.1	✅	The path could not be validated because the end-entity certificate contains the following unsupported critical extension: 1.3.6.1.4.1.55738.666.1
openssl-3.1.6	✅	unhandled critical extension
pyca-cryptography-42.0.8	✅	validation failed: Other("certificate contains unaccounted-for critical extensions: 1.3.6.1.4.1.55738.666.1")
openssl-3.2.2	✅	unhandled critical extension

rfc5280::unknown-critical-extension-root

Produces the following invalid chain:

root -> EE

The root has an extension, 1.3.6.1.4.1.55738.666.1, that no implementation should recognize. As this unrecognized extension is marked as critical, a chain should not be built with this root.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unhandled critical extension
rustls-webpki	✅	trusted certs: trust anchor extraction failed
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate contains an unknown critical extension.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unhandled critical extension
rust-webpki	✅	trusted certs: trust anchor extraction failed
openssl-3.0.14	✅	unhandled critical extension
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	unhandled critical extension
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("certificate contains unaccounted-for critical extensions: 1.3.6.1.4.1.55738.666.1"))
openssl-3.2.2	✅	unhandled critical extension

rfc5280::unknown-critical-extension-intermediate

Produces the following invalid chain:

root -> intermediate (pathlen:0) -> EE

The intermediate has an extension, 1.3.6.1.4.1.55738.666.1, that no implementation should recognize. As this unrecognized extension is marked as critical, a chain should not be built with this intermediate.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unhandled critical extension
rustls-webpki	✅	UnsupportedCriticalExtension
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate contains an unknown critical extension.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unhandled critical extension
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	unhandled critical extension
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 contains the following unsupported critical extension: 1.3.6.1.4.1.55738.666.1
openssl-3.1.6	✅	unhandled critical extension
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("certificate contains unaccounted-for critical extensions: 1.3.6.1.4.1.55738.666.1"))
openssl-3.2.2	✅	unhandled critical extension

rfc5280::chain-untrusted-root

Produces the following chain:

root (untrusted) -> intermediate -> EE

The root is not in the trusted set, thus no chain should be built. Verification can't be achieved without trusted certificates so we add an unrelated root CA to create a more realistic scenario.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	self-signed certificate in certificate chain
rustls-webpki	✅	UnknownIssuer
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate issuer is unknown.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	self signed certificate in certificate chain
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	self-signed certificate in certificate chain
certvalidator-0.11.1	✅	Unable to build a validation path for the certificate "Common Name: example.com" - no issuer matching "Common Name: x509-limbo-root" was found
openssl-3.1.6	✅	self-signed certificate in certificate chain
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("chain construction exceeds max depth"))
openssl-3.2.2	✅	self-signed certificate in certificate chain

rfc5280::intermediate-ca-without-ca-bit

Produces the following invalid chain:

root -> intermediate -> EE

The intermediate CA does not have the cA bit set in BasicConstraints, thus no valid chain to the leaf exists per RFC 5280 4.2.1.9:

If the basic constraints extension is not present in a version 3 certificate, or the extension is present but the cA boolean is not asserted, then the certified public key MUST NOT be used to verify certificate signatures.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	invalid CA certificate
rustls-webpki	✅	EndEntityUsedAsCa
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	invalid CA certificate
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	invalid CA certificate
certvalidator-0.11.1	✅	The path could not be validated because intermediate certificate 1 is not a CA
openssl-3.1.6	✅	invalid CA certificate
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("basicConstraints.cA must be asserted in a CA certificate"))
openssl-3.2.2	✅	invalid CA certificate

rfc5280::intermediate-ca-missing-basic-constraints

Produces the following invalid chain:

root -> ICA -> EE

The intermediate CA is missing the BasicConstraints extension, which is disallowed under RFC 5280 4.2.1.9:

Conforming CAs MUST include this extension in all CA certificates that contain public keys used to validate digital signatures on certificates and MUST mark the extension as critical in such certificates.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unable to get local issuer certificate
rustls-webpki	✅	UnknownIssuer
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate issuer is unknown.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unable to get local issuer certificate
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	unable to get local issuer certificate
certvalidator-0.11.1	✅	Unable to build a validation path for the certificate "Common Name: example.com" - no issuer matching "Common Name: x509-limbo-intermediate-pathlen-None, Organizational Unit: 393828048982174486262897935526193056319953713686" was found
openssl-3.1.6	✅	unable to get local issuer certificate
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("all candidates exhausted with no interior errors"))
openssl-3.2.2	✅	unable to get local issuer certificate

rfc5280::root-missing-basic-constraints

Produces the following invalid chain:

root -> EE

The root CA is missing the BasicConstraints extension, which is disallowed under RFC 5280 4.2.1.9:

Conforming CAs MUST include this extension in all CA certificates that contain public keys used to validate digital signatures on certificates and MUST mark the extension as critical in such certificates.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	invalid CA certificate
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	invalid CA certificate
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	invalid CA certificate
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	invalid CA certificate
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("Certificate is missing required extension"))
openssl-3.2.2	✅	invalid CA certificate

rfc5280::root-non-critical-basic-constraints

Produces the following invalid chain:

root -> EE

The root CA has a non-critical BasicConstraints extension, which is disallowed under RFC 5280 4.2.1.9:

Conforming CAs MUST include this extension in all CA certificates that contain public keys used to validate digital signatures on certificates and MUST mark the extension as critical in such certificates.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	Basic Constraints of CA cert not marked critical
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	Basic Constraints of CA cert not marked critical
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	Basic Constraints of CA cert not marked critical
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("Certificate extension has incorrect criticality"))
openssl-3.2.2	✅	Basic Constraints of CA cert not marked critical

rfc5280::root-inconsistent-ca-extensions

Produces the following invalid chain:

root -> EE

The root CA has BasicConstraints.cA=TRUE and KeyUsage.keyCertSign=FALSE. According to RFC 5280, these two fields are related in the following ways:

If the keyCertSign bit is asserted, then the cA bit in the basic constraints extension MUST also be asserted. (Section 4.2.1.3)

and

If the cA boolean is not asserted, then the keyCertSign bit in the key usage extension MUST NOT be asserted. (Section 4.2.1.9)

Although the profile does not directly state that keyCertSign must be asserted when cA is asserted, this configuration is inconsistent and clients should reject it.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unable to get local issuer certificate
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate chain violates the signer's constraints.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	✅	invalid CA certificate
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	unable to get local issuer certificate
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	unable to get local issuer certificate
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("keyUsage.keyCertSign must be asserted in a CA certificate"))
openssl-3.2.2	✅	unable to get local issuer certificate

rfc5280::ica-ku-keycertsign

Produces the following invalid chain:

root -> ICA -> EE

The intermediate CA includes BasicConstraints with pathLenConstraint=0 and KeyUsage.keyCertSign=FALSE, which is disallowed under RFC 5280 4.2.1.9:

CAs MUST NOT include the pathLenConstraint field unless the cA boolean is asserted and the key usage extension asserts the keyCertSign bit.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unable to get local issuer certificate
rustls-webpki	✅	UnknownIssuer
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The certificate issuer is unknown.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unable to get local issuer certificate
rust-webpki	✅	UnknownIssuer
openssl-3.0.14	✅	unable to get local issuer certificate
certvalidator-0.11.1	✅	Unable to build a validation path for the certificate "Common Name: example.com" - no issuer matching "Common Name: x509-limbo-intermediate-pathlen-0, Organizational Unit: 5121667655987949081704834443484257300699789681" was found
openssl-3.1.6	✅	unable to get local issuer certificate
pyca-cryptography-42.0.8	✅	validation failed: CandidatesExhausted(Other("all candidates exhausted with no interior errors"))
openssl-3.2.2	✅	unable to get local issuer certificate

rfc5280::leaf-ku-keycertsign

Produces the following invalid chain:

root -> EE

The leaf has a BasicConstraints extension with cA=FALSE and a KeyUsage extension with keyCertSign=TRUE. This is disallowed under RFC 5280 4.2.1.9:

The cA boolean indicates whether the certified public key may be used to verify certificate signatures. If the cA boolean is not asserted, then the keyCertSign bit in the key usage extension MUST NOT be asserted.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	Key usage keyCertSign invalid for non-CA cert
rustls-webpki	❌ (unexpected success)	N/A
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	❌ (unexpected success)	N/A
rust-webpki	❌ (unexpected success)	N/A
openssl-3.0.14	✅	Key usage keyCertSign invalid for non-CA cert
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	Key usage keyCertSign invalid for non-CA cert
pyca-cryptography-42.0.8	✅	validation failed: Other("EE keyUsage must not assert keyCertSign")
openssl-3.2.2	✅	Key usage keyCertSign invalid for non-CA cert

rfc5280::ee-aia

Produces a valid chain with an EE cert.

This EE cert contains an Authority Information Access extension with a CA Issuer Access Description.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	✅	N/A
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::ee-critical-aia-invalid

Produces a invalid chain with an EE cert.

This EE cert contains an Authority Information Access extension with a CA Issuer Access Description. The AIA extension is marked as critical, which is disallowed under RFC 5280:

Conforming CAs MUST mark this extension as non-critical.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unhandled critical extension
rustls-webpki	✅	leaf cert: X.509 parse failed
gnutls-certtool-3.7.3	❌ (unexpected success)	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	❌ (unexpected success)	validation: chain built
openssl-1.1	✅	unhandled critical extension
rust-webpki	✅	leaf cert: X.509 parse failed
openssl-3.0.14	✅	unhandled critical extension
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	unhandled critical extension
pyca-cryptography-42.0.8	✅	validation failed: Other("Certificate extension has incorrect criticality")
openssl-3.2.2	✅	unhandled critical extension

rfc5280::duplicate-extensions

Produces the following invalid chain:

root -> EE

This chain is invalid solely because of the EE cert's construction: it contains multiple X.509v3 extensions with the same OID, which is prohibited under RFC 5280 4.2.

A certificate MUST NOT include more than one instance of a particular extension.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	unable to get local issuer certificate
rustls-webpki	✅	leaf cert: X.509 parse failed
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	unable to get local issuer certificate
rust-webpki	✅	leaf cert: X.509 parse failed
openssl-3.0.14	✅	unable to get local issuer certificate
certvalidator-0.11.1	❌ (unexpected success)	N/A
openssl-3.1.6	✅	unable to get local issuer certificate
pyca-cryptography-42.0.8	✅	validation failed: DuplicateExtension(DuplicateExtensionsError(ObjectIdentifier { oid: 2.5.29.17 }))
openssl-3.2.2	✅	unable to get local issuer certificate

rfc5280::no-keyusage

Produces the following valid chain:

root -> EE

The EE lacks a Key Usage extension, which is not required for end-entity certificates under the RFC 5280 profile.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	✅	N/A
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::no-basicconstraints

Produces the following valid chain:

root -> EE

The EE lacks a Basic Constraints extension, which is not required for end-entity certificates under the RFC 5280 profile.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	✅	N/A
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A

rfc5280::mismatching-signature-algorithm

Verifies against a saved copy of cryptography.io's chain with the root certificate modified to have mismatched signatureAlgorithm fields, which is prohibited under RFC 5280 4.2.

A certificate MUST NOT include more than one instance of a particular extension.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	2023-07-10T00:00:00+00:00	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	cert info signature and signature algorithm mismatch
rustls-webpki	✅	leaf cert: X.509 parse failed
gnutls-certtool-3.7.3	✅	N/A
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	certificate signature failure
rust-webpki	✅	leaf cert: X.509 parse failed
openssl-3.0.14	✅	cert info signature and signature algorithm mismatch
certvalidator-0.11.1	✅	The path could not be validated because the signature of the end-entity certificate could not be verified
openssl-3.1.6	✅	cert info signature and signature algorithm mismatch
pyca-cryptography-42.0.8	✅	validation failed: Other("mismatch between signatureAlgorithm and SPKI algorithm")
openssl-3.2.2	✅	cert info signature and signature algorithm mismatch

rfc5280::ca-as-leaf

Produces the following valid chain:

root -> ICA

The ICA is in leaf position, despite being a CA certificate. This is permitted under RFC 5280, which makes no stipulations about CA/EE state in the leaf position.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	webpki::ca-as-leaf	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	❌ (unexpected failure)	CaUsedAsEndEntity
gnutls-certtool-3.7.3	✅	Chain verification output: Verified. The certificate is trusted.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	❌ (unexpected failure)	CaUsedAsEndEntity
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	❌ (unexpected failure)	The X.509 certificate provided is not valid for securing TLS connections
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	🚧	testcase skipped (explicitly unsupported case)
openssl-3.2.2	✅	N/A

rfc5280::ca-as-leaf-wrong-san

Produces the following invalid chain:

root -> ICA

The ICA is in leaf position, despite being a CA certificate. This is permitted under RFC 5280, which makes no stipulations about CA/EE state in the leaf position. However, the ICA also has a different SAN than expected, resulting in a failure.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
FAILURE	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	hostname mismatch
rustls-webpki	✅	CaUsedAsEndEntity
gnutls-certtool-3.7.3	✅	Chain verification output: Not verified. The certificate is NOT trusted. The name in the certificate does not match the expected.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	Hostname mismatch
rust-webpki	✅	CaUsedAsEndEntity
openssl-3.0.14	✅	hostname mismatch
certvalidator-0.11.1	✅	The X.509 certificate provided is not valid for some-other-ca.example.com. Valid hostnames include: ca.example.com
openssl-3.1.6	✅	hostname mismatch
pyca-cryptography-42.0.8	✅	validation failed: Other("basicConstraints.cA must not be asserted in an EE certificate")
openssl-3.2.2	✅	hostname mismatch

rfc5280::root-and-intermediate-swapped

Produces the following valid chain:

root -> ICA -> EE

The configuration puts the ICA in the trusted set, meaning that validation should ignore (and not fail on) the root in the untrusted intermediate set.

Expected result	Validation kind	Validation time	Features	Importance	Conflicts	Download
SUCCESS	SERVER	N/A	N/A	undetermined	N/A	PEM bundle

Harness	Result	Context
openssl-3.3.1	✅	N/A
rustls-webpki	✅	N/A
gnutls-certtool-3.7.3	❌ (unexpected failure)	Chain verification output: Not verified. The certificate is NOT trusted. The certificate issuer is unknown.
gocryptox509-go1.22.5	✅	N/A
openssl-1.1	✅	N/A
rust-webpki	✅	N/A
openssl-3.0.14	✅	N/A
certvalidator-0.11.1	✅	N/A
openssl-3.1.6	✅	N/A
pyca-cryptography-42.0.8	✅	N/A
openssl-3.2.2	✅	N/A