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Changelog

Versions are year-based with a strict backward-compatibility policy. The third digit is only for regressions.

26.0.0 (2026-03-15)

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

25.3.0 (2025-09-16)

Backward-incompatible changes:

Deprecations:

Changes:

  • Maximum supported cryptography version is now 46.x.

25.2.0 (2025-09-14)

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

25.1.0 (2025-05-17)

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.

25.0.0 (2025-01-12)

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.

24.3.0 (2024-11-27)

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.

24.2.1 (2024-07-20)

Backward-incompatible changes:

Deprecations:

Changes:

  • Fixed changelog to remove sphinx specific restructured text strings.

24.2.0 (2024-07-20)

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.

24.1.0 (2024-03-09)

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:

24.0.0 (2024-01-22)

Backward-incompatible changes:

Deprecations:

Changes:

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

23.3.0 (2023-10-25)

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.

23.2.0 (2023-05-30)

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.

23.1.1 (2023-03-28)

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.

23.1.0 (2023-03-24)

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.

23.0.0 (2023-01-01)

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.

22.1.0 (2022-09-25)

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.

22.0.0 (2022-01-29)

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

21.0.0 (2021-09-28)

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

20.0.1 (2020-12-15)

Backward-incompatible changes:

Deprecations:

Changes:

  • Fixed compatibility with OpenSSL 1.1.0.

20.0.0 (2020-11-27)

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

19.1.0 (2019-11-18)

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.

19.0.0 (2019-01-21)

Backward-incompatible changes:

  • X509Store.add_cert no longer raises an error if you add a duplicate cert. #787

Deprecations:

none

Changes:

  • pyOpenSSL now works with OpenSSL 1.1.1. #805
  • pyOpenSSL now handles NUL bytes in X509Name.get_components() #804

18.0.0 (2018-05-16)

Backward-incompatible changes:

  • The minimum cryptography version is now 2.2.1.
  • Support for Python 2.6 has been dropped.

Deprecations:

none

Changes:

  • Added Connection.get_certificate to retrieve the local certificate. #733
  • OpenSSL.SSL.Connection now sets SSL_MODE_AUTO_RETRY by default. #753
  • Added Context.set_tlsext_use_srtp to enable negotiation of SRTP keying material. #734

17.5.0 (2017-11-30)

Backward-incompatible changes:

  • The minimum cryptography version is now 2.1.4.

Deprecations:

none

Changes:

  • Fixed a potential use-after-free in the verify callback and resolved a memory leak when loading PKCS12 files with cacerts. #723
  • Added Connection.export_keying_material for RFC 5705 compatible export of keying material. #725

17.4.0 (2017-11-21)

Backward-incompatible changes:

none

Deprecations:

none

Changes:

  • Re-added a subset of the OpenSSL.rand module. This subset allows conscientious users to reseed the OpenSSL CSPRNG after fork. #708
  • Corrected a use-after-free when reusing an issuer or subject from an X509 object after the underlying object has been mutated. #709

17.3.0 (2017-09-14)

Backward-incompatible changes:

  • Dropped support for Python 3.3. #677
  • Removed the deprecated OpenSSL.rand module. This is being done ahead of our normal deprecation schedule due to its lack of use and the fact that it was becoming a maintenance burden. os.urandom() should be used instead. #675

Deprecations:

  • Deprecated OpenSSL.tsafe. #673

Changes:

  • Fixed a memory leak in OpenSSL.crypto.CRL. #690
  • Fixed a memory leak when verifying certificates with OpenSSL.crypto.X509StoreContext. #691

17.2.0 (2017-07-20)

Backward-incompatible changes:

none

Deprecations:

  • Deprecated OpenSSL.rand - callers should use os.urandom() instead. #658

Changes:

  • Fixed a bug causing Context.set_default_verify_paths() to not work with cryptography manylinux1 wheels on Python 3.x. #665
  • Fixed a crash with (EC)DSA signatures in some cases. #670

17.1.0 (2017-06-30)

Backward-incompatible changes:

  • Removed the deprecated OpenSSL.rand.egd() function. Applications should prefer os.urandom() for random number generation. #630
  • Removed the deprecated default digest argument to OpenSSL.crypto.CRL.export(). Callers must now always pass an explicit digest. #652
  • Fixed a bug with ASN1_TIME casting in X509.set_notBefore(), X509.set_notAfter(), Revoked.set_rev_date(), Revoked.set_nextUpdate(), and Revoked.set_lastUpdate(). You must now pass times in the form YYYYMMDDhhmmssZ. YYYYMMDDhhmmss+hhmm and YYYYMMDDhhmmss-hhmm will no longer work. #612

Deprecations:

  • Deprecated the legacy "Type" aliases: ContextType, ConnectionType, PKeyType, X509NameType, X509ExtensionType, X509ReqType, X509Type, X509StoreType, CRLType, PKCS7Type, PKCS12Type, NetscapeSPKIType. The names without the "Type"-suffix should be used instead.

Changes:

  • Added OpenSSL.crypto.X509.from_cryptography() and OpenSSL.crypto.X509.to_cryptography() for converting X.509 certificate to and from pyca/cryptography objects. #640
  • Added OpenSSL.crypto.X509Req.from_cryptography(), OpenSSL.crypto.X509Req.to_cryptography(), OpenSSL.crypto.CRL.from_cryptography(), and OpenSSL.crypto.CRL.to_cryptography() for converting X.509 CSRs and CRLs to and from pyca/cryptography objects. #645
  • Added OpenSSL.debug that allows to get an overview of used library versions (including linked OpenSSL) and other useful runtime information using python -m OpenSSL.debug. #620
  • Added a fallback path to Context.set_default_verify_paths() to accommodate the upcoming release of cryptography manylinux1 wheels. #633

17.0.0 (2017-04-20)

Backward-incompatible changes:

none

Deprecations:

none

Changes:

  • Added OpenSSL.X509Store.set_time() to set a custom verification time when verifying certificate chains. #567
  • Added a collection of functions for working with OCSP stapling. None of these functions make it possible to validate OCSP assertions, only to staple them into the handshake and to retrieve the stapled assertion if provided. Users will need to write their own code to handle OCSP assertions. We specifically added: Context.set_ocsp_server_callback(), Context.set_ocsp_client_callback(), and Connection.request_ocsp(). #580
  • Changed the SSL module's memory allocation policy to avoid zeroing memory it allocates when unnecessary. This reduces CPU usage and memory allocation time by an amount proportional to the size of the allocation. For applications that process a lot of TLS data or that use very lage allocations this can provide considerable performance improvements. #578
  • Automatically set SSL_CTX_set_ecdh_auto() on OpenSSL.SSL.Context. #575
  • Fix empty exceptions from OpenSSL.crypto.load_privatekey(). #581

16.2.0 (2016-10-15)

Backward-incompatible changes:

none

Deprecations:

none

Changes:

  • Fixed compatibility errors with OpenSSL 1.1.0.
  • Fixed an issue that caused failures with subinterpreters and embedded Pythons. #552

16.1.0 (2016-08-26)

Backward-incompatible changes:

none

Deprecations:

  • Dropped support for OpenSSL 0.9.8.

Changes:

  • Fix memory leak in OpenSSL.crypto.dump_privatekey() with FILETYPE_TEXT. #496
  • Enable use of CRL (and more) in verify context. #483
  • OpenSSL.crypto.PKey can now be constructed from cryptography objects and also exported as such. #439
  • Support newer versions of cryptography which use opaque structs for OpenSSL 1.1.0 compatibility.

16.0.0 (2016-03-19)

This is the first release under full stewardship of PyCA. We have made many changes to make local development more pleasing. The test suite now passes both on Linux and OS X with OpenSSL 0.9.8, 1.0.1, and 1.0.2. It has been moved to pytest, all CI test runs are part of tox and the source code has been made fully flake8 compliant.

We hope to have lowered the barrier for contributions significantly but are open to hear about any remaining frustrations.

Backward-incompatible changes:

  • Python 3.2 support has been dropped. It never had significant real world usage and has been dropped by our main dependency cryptography. Affected users should upgrade to Python 3.3 or later.

Deprecations:

  • The support for EGD has been removed. The only affected function OpenSSL.rand.egd() now uses os.urandom() to seed the internal PRNG instead. Please see pyca/cryptography#1636 for more background information on this decision. In accordance with our backward compatibility policy OpenSSL.rand.egd() will be removed no sooner than a year from the release of 16.0.0.

    Please note that you should use urandom for all your secure random number needs.

  • Python 2.6 support has been deprecated. Our main dependency cryptography deprecated 2.6 in version 0.9 (2015-05-14) with no time table for actually dropping it. pyOpenSSL will drop Python 2.6 support once cryptography does.

Changes:

  • Fixed OpenSSL.SSL.Context.set_session_id, OpenSSL.SSL.Connection.renegotiate, OpenSSL.SSL.Connection.renegotiate_pending, and OpenSSL.SSL.Context.load_client_ca. They were lacking an implementation since 0.14. #422
  • Fixed segmentation fault when using keys larger than 4096-bit to sign data. #428
  • Fixed AttributeError when OpenSSL.SSL.Connection.get_app_data() was called before setting any app data. #304
  • Added OpenSSL.crypto.dump_publickey() to dump OpenSSL.crypto.PKey objects that represent public keys, and OpenSSL.crypto.load_publickey() to load such objects from serialized representations. #382
  • Added OpenSSL.crypto.dump_crl() to dump a certificate revocation list out to a string buffer. #368
  • Added OpenSSL.SSL.Connection.get_state_string() using the OpenSSL binding state_string_long. #358
  • Added support for the socket.MSG_PEEK flag to OpenSSL.SSL.Connection.recv() and OpenSSL.SSL.Connection.recv_into(). #294
  • Added OpenSSL.SSL.Connection.get_protocol_version() and OpenSSL.SSL.Connection.get_protocol_version_name(). #244
  • Switched to utf8string mask by default. OpenSSL formerly defaulted to a T61String if there were UTF-8 characters present. This was changed to default to UTF8String in the config around 2005, but the actual code didn't change it until late last year. This will default us to the setting that actually works. To revert this you can call OpenSSL.crypto._lib.ASN1_STRING_set_default_mask_asc(b"default"). #234

Older Changelog Entries

The changes from before release 16.0.0 are preserved in the repository.
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