cryptography is a package designed to expose cryptographic primitives and recipes to Python developers. Prior to 49.0.0, if an intermediate constrained CA permits the DNS name foo.example.com, and the leaf certificate has a wildcard in its DNS SAN of *.example.com, python-cryptography's verifier accepts which allows escaping outside of the permitted names. The core issue is in DNSConstraint::matches, where a wildcard pattern was treated as matching a more-specific permitted constraint even though *.example.com can expand to sibling names such as bar.example.com outside foo.example.com. This allows acceptance of an invalid certificate chain. This issue is fixed in 49.0.0.

python-cryptography is a package designed to expose cryptographic primitives and recipes to Python developers. Prior to 49.0.0, when resolving invalid certificate chains that include duplicate copies of self-signed certificates, the processing recursively invokes the same candidate, leading to an exponential blowup. Although the limitation that the chain depth cannot exceed a specified maximum depth prevents unbounded recursion and guarantees termination, an attacker-controlled certificate chain can lead the processing to easily take more than 5s to reject in testing. This amplification could form the basis for a resource exhaustion denial of service attack. The core issue arises in the recursive nature of build_chain_inner, which does not de-duplicate against previously analyzed candidates. As the correctness of validation is not affected, the integrity of a system cannot be compromised through this vector, only its availability. This issue is fixed in 49.0.0.

cryptography is a package designed to expose cryptographic primitives and recipes to Python developers. From 44.0.0 until 50.0.0, pkcs7_decrypt_der, pkcs7_decrypt_pem, and pkcs7_decrypt_smime reported the outcome of decrypting a RecipientInfo's encryptedKey in several distinguishable ways, one of which disclosed the exact length recovered from the RSA operation. The same distinction was also observable by timing. An application that decrypts attacker-supplied EnvelopedData and reflects the outcome gives the attacker a Bleichenbacher oracle against the content-encryption key. Decryption ran as RSA PKCS#1 v1.5 decrypt of encryptedKey, build an AES cipher from the result, then AES-CBC decrypt and PKCS#7 unpad. Invalid RSA padding, a valid padding with a bad key length, a correct length with a wrong key, and the real key each failed or succeeded differently. Case 1 is reachable only where the linked library lacks implicit rejection: OpenSSL 3.0 and 3.1, LibreSSL, and BoringSSL. Exploitation requires a service that auto-decrypts untrusted EnvelopedData matching the victim certificate and answers adaptively at high volume, such as an S/MIME gateway or mail filter. This issue is fixed in 50.0.0.