cryptography: PKCS#7 EnvelopedData decryption exposes a Bleichenbacher oracle through distinguishable errors and timing

Summary

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.

Timeline

1. Aug 3, 2026, 9:16 PM UTCCVE published
2. Aug 4, 2026, 2:09 PM UTCCISA SSVC assessment

   Exploitation: none · Automatable: no · Technical impact: partial

3. Aug 4, 2026, 2:09 PM UTCRecord last updated

Affected versions

• pyca cryptography

  From 44.0.0 · fixed in 50.0.0

• cryptographyPyPI

  From 44.0.0 · fixed in 50.0.0

References 3