GHSA-g6cj-pr64-35w5

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    GHSA-g6cj-pr64-35w5

    Published: 3 Aug 2026Last Modified: 4 Aug 2026

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

    Details: ### Summary `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. Introduced in 44.0.0. Fixed in 50.0.0. ### Details Decryption ran as: RSA PKCS#1 v1.5 decrypt of `encryptedKey` → build an AES cipher from the result → AES-CBC decrypt and PKCS#7 unpad. Each stage failed differently, with no RFC 3218 mitigation: 1. invalid RSA padding → `Decryption failed` 2. valid padding, bad key length → `Invalid key size (N) for AES.`, disclosing `N` 3. correct length, wrong key → `Invalid padding bytes.` 4. the real key → plaintext Case 1 is reachable only where the linked library lacks implicit rejection: OpenSSL 3.0 and 3.1, LibreSSL, and BoringSSL. On OpenSSL 3.2+, used in our wheels, invalid padding instead returns a synthetic plaintext of pseudorandom length, so the error channel does not distinguish conforming ciphertexts. 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. ### Fix Per RFC 3218, the content-encryption algorithm is now resolved before the private key is used, so the expected key length is known in advance. If the RSA decryption fails or recovers a key of the wrong length, a random key of the expected length is substituted and decryption continues down an identical path. All failures now report identically and perform the same work. ### Not addressed by this fix `EnvelopedData` does not authenticate its content. Tampering with `encryptedContent` alone yields a CBC padding oracle that recovers plaintext at roughly 256 queries per byte, without recovering any key, on every backend. This is a property of PKCS#7 rather than of this implementation, cannot be fixed in the library, and is now documented. ### Credit Reported by @X1AOxiang.

    Affected packages

    Package

    Name: cryptography

    Purl: pkg:pypi/cryptography

    Affected ranges

    Type: ECOSYSTEM

    Events:

    Introduced- 44.0.0
    Fixed -50.0.0

    Affected versions

    44.0.0
    44.0.1
    44.0.2
    44.0.3

    Common Vulnerability Scoring System

    Attack Vector
    Network
    Adjacent
    Local
    Physical
    Privileges Required
    None
    Low
    High
    User Interaction
    None
    Required
    Scope
    Unchanged
    Changed
    Confidentiality
    None
    Low
    High
    Integrity
    None
    Low
    High
    Availability
    None
    Low
    High