Backward-incompatible changes:

Deprecations:

Changes:

• Maximum supported cryptography version is now 50.x.

Backward-incompatible changes:

• Dropped support for Python 3.8.

• The minimum cryptography version is now 49.0.0.

• Removed deprecated OpenSSL.crypto.X509Req, OpenSSL.crypto.dump_certificate_request, and OpenSSL.crypto.load_certificate_request. cryptography.x509 should be used instead.

• OpenSSL.SSL.Connection.set_session now raises ValueError if the Session was obtained from a Connection that was using a different Context than this one. OpenSSL requires (but does not verify) that sessions only be re-used with a compatible SSL_CTX, so this contract is now enforced.

Deprecations:

• Deprecated OpenSSL.crypto.PKey.generate_key and OpenSSL.crypto.PKey.check. The key generation and loading APIs in cryptography should be used instead.

• Deprecated OpenSSL.crypto.dump_privatekey. The serialization APIs on cryptography private key types should be used instead.

• Deprecated all the mutable APIs on OpenSSL.crypto.X509: set_version, set_pubkey, sign, set_serial_number, gmtime_adj_notAfter, gmtime_adj_notBefore, set_notBefore, set_notAfter, set_issuer, and set_subject. cryptography.x509.CertificateBuilder should be used instead.

• Deprecated OpenSSL.SSL.Context.set_passwd_cb. Users should decrypt and load their private keys themselves, with cryptography’s key loading APIs, and then call OpenSSL.SSL.Context.use_privatekey.

• Deprecated OpenSSL.crypto.X509Name, as well as the remaining APIs that consume or return it: OpenSSL.crypto.X509.get_issuer, OpenSSL.crypto.X509.get_subject, and OpenSSL.SSL.Context.set_client_ca_list. The APIs in cryptography.x509 should be used instead.

Changes:

• OpenSSL.SSL.Connection.get_client_ca_list now takes an as_cryptography keyword-argument. When True is passed then cryptography.x509.Name are returned, instead of OpenSSL.crypto.X509Name. In the future, passing False (the default) will be deprecated.

Backward-incompatible changes:

• Removed deprecated OpenSSL.crypto.X509Extension, OpenSSL.crypto.X509Req.add_extension, OpenSSL.crypto.X509Req.get_extensions, OpenSSL.crypto.X509.add_extension, OpenSSL.crypto.X509.get_extensions. cryptography.x509 should be used instead.

• It is now an error to calling any mutating method on OpenSSL.SSL.Context after it has been used to create a Connection. This was previously deprecated and has always been unsafe.

Deprecations:

Changes:

• Maximum supported cryptography version is now 48.x.

• Added OpenSSL.SSL.Connection.set_options to set options on a per-connection basis.

Backward-incompatible changes:

Deprecations:

Changes:

• Maximum supported cryptography version is now 47.x.

• Fixed X509Name field setters to correctly pass the value length to OpenSSL. Previously, values containing NUL bytes would be silently truncated, causing a divergence between the stored ASN.1 value and the value visible from Python. Credit to BudongJW for reporting the issue. CVE-2026-40475

Backward-incompatible changes:

• Dropped support for Python 3.7.

• The minimum cryptography version is now 46.0.0.

Deprecations:

Changes:

• Added support for using aws-lc instead of OpenSSL.

• Properly raise an error if a DTLS cookie callback returned a cookie longer than DTLS1_COOKIE_LENGTH bytes. Previously this would result in a buffer-overflow. Credit to dark_haxor for reporting the issue. CVE-2026-27459

• Added OpenSSL.SSL.Connection.get_group_name to determine which group name was negotiated.

• Context.set_tlsext_servername_callback now handles exceptions raised in the callback by calling sys.excepthook and returning a fatal TLS alert. Previously, exceptions were silently swallowed and the handshake would proceed as if the callback had succeeded. Credit to Leury Castillo for reporting this issue. CVE-2026-27448

Backward-incompatible changes:

Deprecations:

Changes:

• Maximum supported cryptography version is now 46.x.

Backward-incompatible changes:

• The minimum cryptography version is now 45.0.7.

Deprecations:

Changes:

• pyOpenSSL now sets SSL_MODE_ACCEPT_MOVING_WRITE_BUFFER on connections by default, matching CPython’s behavior.

• Added OpenSSL.SSL.Context.clear_mode.

• Added OpenSSL.SSL.Context.set_tls13_ciphersuites to set the allowed TLS 1.3 ciphers.

• Added OpenSSL.SSL.Connection.set_info_callback

Backward-incompatible changes:

Deprecations:

• Attempting using any methods that mutate an OpenSSL.SSL.Context after it has been used to create an OpenSSL.SSL.Connection will emit a warning. In a future release, this will raise an exception.

Changes:

• cryptography maximum version has been increased to 45.0.x.

Backward-incompatible changes:

Deprecations:

Changes:

• Corrected type annotations on Context.set_alpn_select_callback, Context.set_session_cache_mode, Context.set_options, Context.set_mode, X509.subject_name_hash, and X509Store.load_locations.

• Deprecated APIs are now marked using warnings.deprecated. mypy will emit deprecation notices for them when used with --enable-error-code deprecated.

Backward-incompatible changes:

• Removed the deprecated OpenSSL.crypto.CRL, OpenSSL.crypto.Revoked, OpenSSL.crypto.dump_crl, and OpenSSL.crypto.load_crl. cryptography.x509’s CRL functionality should be used instead.

• Removed the deprecated OpenSSL.crypto.sign and OpenSSL.crypto.verify. cryptography.hazmat.primitives.asymmetric’s signature APIs should be used instead.

Deprecations:

• Deprecated OpenSSL.rand - callers should use os.urandom() instead.

• Deprecated add_extensions and get_extensions on OpenSSL.crypto.X509Req and OpenSSL.crypto.X509. These should have been deprecated at the same time X509Extension was. Users should use pyca/cryptography’s X.509 APIs instead.

• Deprecated OpenSSL.crypto.get_elliptic_curves and OpenSSL.crypto.get_elliptic_curve, as well as passing the reult of them to OpenSSL.SSL.Context.set_tmp_ecdh, users should instead pass curves from cryptography.

• Deprecated passing X509 objects to OpenSSL.SSL.Context.use_certificate, OpenSSL.SSL.Connection.use_certificate, OpenSSL.SSL.Context.add_extra_chain_cert, and OpenSSL.SSL.Context.add_client_ca, users should instead pass cryptography.x509.Certificate instances. This is in preparation for deprecating pyOpenSSL’s X509 entirely.

• Deprecated passing PKey objects to OpenSSL.SSL.Context.use_privatekey and OpenSSL.SSL.Connection.use_privatekey, users should instead pass cryptography private key instances. This is in preparation for deprecating pyOpenSSL’s PKey entirely.

Changes:

• cryptography maximum version has been increased to 44.0.x.

• OpenSSL.SSL.Connection.get_certificate, OpenSSL.SSL.Connection.get_peer_certificate, OpenSSL.SSL.Connection.get_peer_cert_chain, and OpenSSL.SSL.Connection.get_verified_chain now take an as_cryptography keyword-argument. When True is passed then cryptography.x509.Certificate are returned, instead of OpenSSL.crypto.X509. In the future, passing False (the default) will be deprecated.

Backward-incompatible changes:

Deprecations:

Changes:

• Fixed changelog to remove sphinx specific restructured text strings.

Backward-incompatible changes:

Deprecations:

• Deprecated OpenSSL.crypto.X509Req, OpenSSL.crypto.load_certificate_request, OpenSSL.crypto.dump_certificate_request. Instead, cryptography.x509.CertificateSigningRequest, cryptography.x509.CertificateSigningRequestBuilder, cryptography.x509.load_der_x509_csr, or cryptography.x509.load_pem_x509_csr should be used.

Changes:

• Added type hints for the SSL module. #1308.

• Changed OpenSSL.crypto.PKey.from_cryptography_key to accept public and private EC, ED25519, ED448 keys. #1310.

Backward-incompatible changes:

• Removed the deprecated OpenSSL.crypto.PKCS12 and OpenSSL.crypto.NetscapeSPKI. OpenSSL.crypto.PKCS12 may be replaced by the PKCS#12 APIs in the cryptography package.

Deprecations:

Changes:

Backward-incompatible changes:

Deprecations:

Changes:

• Added OpenSSL.SSL.Connection.get_selected_srtp_profile to determine which SRTP profile was negotiated. #1279.

Backward-incompatible changes:

• Dropped support for Python 3.6.

• The minimum cryptography version is now 41.0.5.

• Removed OpenSSL.crypto.load_pkcs7 and OpenSSL.crypto.load_pkcs12 which had been deprecated for 3 years.

• Added OpenSSL.SSL.OP_LEGACY_SERVER_CONNECT to allow legacy insecure renegotiation between OpenSSL and unpatched servers. #1234.

Deprecations:

• Deprecated OpenSSL.crypto.PKCS12 (which was intended to have been deprecated at the same time as OpenSSL.crypto.load_pkcs12).

• Deprecated OpenSSL.crypto.NetscapeSPKI.

• Deprecated OpenSSL.crypto.CRL

• Deprecated OpenSSL.crypto.Revoked

• Deprecated OpenSSL.crypto.load_crl and OpenSSL.crypto.dump_crl

• Deprecated OpenSSL.crypto.sign and OpenSSL.crypto.verify

• Deprecated OpenSSL.crypto.X509Extension

Changes:

• Changed OpenSSL.crypto.X509Store.add_crl to also accept cryptography’s x509.CertificateRevocationList arguments in addition to the now deprecated OpenSSL.crypto.CRL arguments.

• Fixed test_set_default_verify_paths test so that it is skipped if no network connection is available.

Backward-incompatible changes:

• Removed X509StoreFlags.NOTIFY_POLICY. #1213.

Deprecations:

Changes:

• cryptography maximum version has been increased to 41.0.x.

• Invalid versions are now rejected in OpenSSL.crypto.X509Req.set_version.

• Added X509VerificationCodes to OpenSSL.SSL. #1202.

Backward-incompatible changes:

Deprecations:

Changes:

• Worked around an issue in OpenSSL 3.1.0 which caused X509Extension.get_short_name to raise an exception when no short name was known to OpenSSL. #1204.

Backward-incompatible changes:

Deprecations:

Changes:

• cryptography maximum version has been increased to 40.0.x.

• Add OpenSSL.SSL.Connection.DTLSv1_get_timeout and OpenSSL.SSL.Connection.DTLSv1_handle_timeout to support DTLS timeouts #1180.

Backward-incompatible changes:

Deprecations:

Changes:

• Add OpenSSL.SSL.X509StoreFlags.PARTIAL_CHAIN constant to allow for users to perform certificate verification on partial certificate chains. #1166

• cryptography maximum version has been increased to 39.0.x.

Backward-incompatible changes:

• Remove support for SSLv2 and SSLv3.

• The minimum cryptography version is now 38.0.x (and we now pin releases against cryptography major versions to prevent future breakage)

• The OpenSSL.crypto.X509StoreContextError exception has been refactored, changing its internal attributes. #1133

Deprecations:

• OpenSSL.SSL.SSLeay_version is deprecated in favor of OpenSSL.SSL.OpenSSL_version. The constants OpenSSL.SSL.SSLEAY_* are deprecated in favor of OpenSSL.SSL.OPENSSL_*.

Changes:

• Add OpenSSL.SSL.Connection.set_verify and OpenSSL.SSL.Connection.get_verify_mode to override the context object’s verification flags. #1073

• Add OpenSSL.SSL.Connection.use_certificate and OpenSSL.SSL.Connection.use_privatekey to set a certificate per connection (and not just per context) #1121.

Backward-incompatible changes:

• Drop support for Python 2.7. #1047

• The minimum cryptography version is now 35.0.

Deprecations:

Changes:

• Expose wrappers for some DTLS primitives. #1026

Backward-incompatible changes:

• The minimum cryptography version is now 3.3.

• Drop support for Python 3.5

Deprecations:

Changes:

• Raise an error when an invalid ALPN value is set. #993

• Added OpenSSL.SSL.Context.set_min_proto_version and OpenSSL.SSL.Context.set_max_proto_version to set the minimum and maximum supported TLS version #985.

• Updated to_cryptography and from_cryptography methods to support an upcoming release of cryptography without raising deprecation warnings. #1030

Backward-incompatible changes:

Deprecations:

Changes:

• Fixed compatibility with OpenSSL 1.1.0.

Backward-incompatible changes:

• The minimum cryptography version is now 3.2.

• Remove deprecated OpenSSL.tsafe module.

• Removed deprecated OpenSSL.SSL.Context.set_npn_advertise_callback, OpenSSL.SSL.Context.set_npn_select_callback, and OpenSSL.SSL.Connection.get_next_proto_negotiated.

• Drop support for Python 3.4

• Drop support for OpenSSL 1.0.1 and 1.0.2

Deprecations:

• Deprecated OpenSSL.crypto.load_pkcs7 and OpenSSL.crypto.load_pkcs12.

Changes:

• Added a new optional chain parameter to OpenSSL.crypto.X509StoreContext() where additional untrusted certificates can be specified to help chain building. #948

• Added OpenSSL.crypto.X509Store.load_locations to set trusted certificate file bundles and/or directories for verification. #943

• Added Context.set_keylog_callback to log key material. #910

• Added OpenSSL.SSL.Connection.get_verified_chain to retrieve the verified certificate chain of the peer. #894.

• Make verification callback optional in Context.set_verify. If omitted, OpenSSL’s default verification is used. #933

• Fixed a bug that could truncate or cause a zero-length key error due to a null byte in private key passphrase in OpenSSL.crypto.load_privatekey and OpenSSL.crypto.dump_privatekey. #947

Backward-incompatible changes:

• Removed deprecated ContextType, ConnectionType, PKeyType, X509NameType, X509ReqType, X509Type, X509StoreType, CRLType, PKCS7Type, PKCS12Type, and NetscapeSPKIType aliases. Use the classes without the Type suffix instead. #814

• The minimum cryptography version is now 2.8 due to issues on macOS with a transitive dependency. #875

Deprecations:

• Deprecated OpenSSL.SSL.Context.set_npn_advertise_callback, OpenSSL.SSL.Context.set_npn_select_callback, and OpenSSL.SSL.Connection.get_next_proto_negotiated. ALPN should be used instead. #820

Changes:

• Support bytearray in SSL.Connection.send() by using cffi’s from_buffer. #852

• The OpenSSL.SSL.Context.set_alpn_select_callback can return a new NO_OVERLAPPING_PROTOCOLS sentinel value to allow a TLS handshake to complete without an application protocol.

Full changelog.