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CHANGELOG

2.4.0 (2026-09-04)

  • enh: relax IO class requirements for attachments
  • feat: allow local MTA instead of SMTP, using traditional sendmail command
  • fix (security): close jsonpickle RCE, argv injection, and parser recursion DoS
  • feat (docs): new documentation site (mkdocs), split from README

2.3.1 (2026-03-04)

  • fix (smtp): password timeout crash #52

2.3.0 (2025-07-19)

  • feat: allow certificate chains in S/MIME Signatures #51
  • enh: obfuscate password from logs

2.2.1 (2025-05-23)

  • feat: Experimental ._check_auth method

2.2.0 (2025-03-25)

  • Licence change from GPL-3.0-or-later to LGPL-3.0-or-later.

2.1.1 (2025-02-19)

  • fix addresses for older python patched versions (< 3.12.3, < 3.11.?) #45

2.1.0 (2025-01-17)

  • reworked s/mime cryptography

2.0.4 (2024-07-18)

  • resilience against missing libmagic (useful on a contained environment)
  • better SMTP retries #35
  • better typing #31
  • fix: attachment included while signing only (without sending)

2.0.3 (2024-01-03)

  • fix: loading headers not encoded with utf-8
  • fix: better S/MIME detection #29
  • drop Python 3.9 support
  • SMTP HELO FQDN

2.0.2 (2022-11-25)

  • experimental XARF reports reading
  • disguised addresses parsing

2.0.1 (2022-11-21)

  • fix #24 stable locale
  • allow file-magic instead of python-magic package be installed on the system (#25)
  • fix GPG signing when attaching file with name longer than 34 chars (#19)

2.0.0 (2022-05-04)

  • CHANGED: Envelope(sender=).sender() alias REMOVED because to the unambiguous naming clash between the From and the Sender e-mail header. Use Envelope().from_(...) and Envelope().header("Sender", ...) instead. Pity that 'from' is a reserved keyword, "from_" looks bad.
  • CHANGED: Envelope.default instance REMOVED because explicit is better than implicit. For setting defaults use Envelope().copy() instead
  • CHANGED: explicitly specifying encryption keys prevents encrypting for other recipients
  • GPG encryption for arbitrary keys only possible #9 #14
  • CHANGED: Optional parameter "email_or_list" renamed to "email_or_more" (methods to and friends)
  • When setting recipients, apart from list other iterables (tuple, generator, set, ...) may be used
  • fix: when signing key fails, do not sign with the default GPG private key
  • S/MIME insecure Rand PRNG removed #18

1.5.4 (2022-04-04)

  • disable validate_email module blacklist updater #17
  • SMTP envelope MAIL FROM address #16
  • SMTP exposes timeout #20 , attempts, delay
  • SMTP re-connect on every error #21
  • smtp.quit() exposed #5

1.5.3 (2021-08-02)

  • group syntax is no more reported as erroneous (ex: undisclosed-recipients:;)

1.5.2 (2021-06-02)

  • better invalid header loading (ex: invalid charset in the content type header)
  • SMTP connection uses ssl.create_default_context() by default

1.5.1 (2021-03-04)

  • choose subject text placeholder while PGP encrypting
  • fix sending e-mail without From if deliberately set to False (regression)

1.5 (2021-02-09)

– Address properties are "" if empty (handy when comparing strings) - replace invalid characters when loading (the way the e-mail clients behave) - headers truly case-insensitive when loading - .from_() and .sender() truly return an Address even if not set (and then the Address is empty) - fix: the internal cache correctly regenerated - message is internally held in bytes -> helpful error message when charset fails

1.4 (2021-01-23)

  • exposed Address
  • Address casefold method and user and host properties
  • loading ignores invalid headers (and prints out a warning)

1.3.3 (2021-01-21)

  • fix case-insensitive header loading
  • fix non-latin chars in header loading

1.3.2 (2020-10-26)

  • fix charset for base64 encoded content
  • fix the default encoding while casting an attachment to string

1.3 (2020-10-05)

  • CHANGED:
    • .attach(filename=) renamed to .attach(name=)
    • --attachment renamed to --attach
    • .to(), .cc(), .bcc(), .from_(), .sender(), .reply_to(), .recipients() now return an Address object(s), not str
  • .as_message -> Message
  • e-mail validation
  • proper e-mail addresses handling: they can be in a string delimited by comma (or semicolon)
  • text alternatives
  • fix encoded headers
  • fix attainable contents fetching
  • embedding inline images
  • loading parses attachments and decrypts
  • contacts might be cleared (ex: to clear To header intuitively type .to(False))
  • .attachments, --attachments [NAME] -> read the list of the attachments
  • preview returns nicely formatted headers

1.2 (2020-06-18)

  • fix: smtplib.SMTP_SSL handshake operation timed out caught
  • if a line is longer than 1000 characters, makes the message be transferred safely by bytes (which would not break up DKIM)
  • when "Content-Transfer-Encoding" is set to "base64" or "quo-pri" and reading message, it gets decoded (useful when loading EML files cat file.eml | envelope --message)
  • preview method available from CLI

1.1 (2020-05-30)

  • fix: default object
  • better EML files loading
  • generic header manipulation (removing, adding multiple, mostly preserves order when loading)
  • reply-to allows multiple addresses

1.0.0 (2020-05-28)

  • CHANGED:
    • Envelope.init parameters re-ordered
    • from envelope import Envelope is the only right way to import, import envelope no more supported (slightly longer, however better suits Python naming conventions)
  • fix: --attach-key flag in CLI did not work
  • auto-import GPG key from file
  • auto-encrypt GPG possibility
  • S/MIME multiple recipients
  • "sender" works as an alias for "from_" if both are not used; otherwise standard "Sender" header is included
  • .date(date) method allows turn off automatic Date header adding
  • fix: object is modified whenever a parameter changes (ex: if user changes subject multiple times), not at send time
  • .message has new aliases: .body and .text to facilitate the programmer's workflow because when autocomplete

0.9.9 (2020-02-10)

  • smime dependency is optional – thus package can be installed directly without having swig library

0.9.8 (2020-01-27)

  • set signing to "auto" for signing if there is a key matching to the "from" header
  • preview method
  • recipients method
  • read subject(), message()
  • load method

0.9.7 (2020-01-17)

  • choose mime subtype (html or plain) + conditional conversion of line breaks to
    #4
  • experimental load function to create e-mail object from text templates
  • fix: possibility to include own "Content-Type" into headers

0.9.6 (2020-01-14)

  • fix: Subject tried to be re-set when no GPG neither S/MIME used

0.9.5 (2019-12-12)

  • CHANGED:
    • encrypt-file changed to encrypt-path (to match the encrypt_path parameter of the encrypt method)
    • parameter swap from .encrypt(sign=None, key=True) to .encrypt(key=True, sign=None) due to S/MIME that does not take the key from the GPG keyring but needs the certificate to be specified every time.
  • S\MIME
    • signing (M2Crypto instead of smime package)
    • insert subject while encrypting
  • unit tests + travis build status
  • SMTP
    • if SMTP/INI file is given as a relative path and not found at CWD, we try program directory (useful when importing Envelope as a library from another program)
    • TLS security supported
    • if security not defined, determined by port
  • bash completion
  • --quiet flag

0.9.4 (2019-12-03)

  • fix launching with no flags (bare message erroneously tried to be GPG-signed by default)

0.9.3 (2019-11-30)

  • attachment file not found caught
  • output attached to the complex example in the README
  • fix launched in a loop

0.9.2

  • CLI: if nothing to do, assume parameters are a bone of an e-mail message to produce output
  • check GPG signing failed
  • fix GnuPG home
  • fix encrypted subject
  • SMTP supports INI file
  • check will print out DNS information of the sender's domain
  • CLI: metavar display names added
  • attach_key flag added

0.9.1

  • signing, encrypting, sending
  • GPG, S/MIME support
  • cli, one-liner, fluent interface
  • SMTP reconnection