id	summary	reporter	owner	description	type	status	component	version	severity	resolution	keywords	cc	stage	has_patch	needs_docs	needs_tests	needs_better_patch	easy	ui_ux
36119	Attaching email file to email fails if the attachment is using 8bit Content-Transfer-Encoding	Trenton H	Gregory Mariani	"If the attached email file is attached to an email, such as the code snipped below, the sending will fail due to the presence of non-ASCII content in the attachment.

{{{#!python
email = EmailMessage(
    subject=""subject"",
    body=""body"",
    to=""someone@somewhere.com"",
)
email.attach_file(original_file)
n_messages = email.send()
}}}

{{{
Traceback (most recent call last):
  File ""/usr/src/paperless/src/documents/signals/handlers.py"", line 989, in email_action
    n_messages = email.send()
                 ^^^^^^^^^^^^
  File ""/usr/local/lib/python3.12/site-packages/django/core/mail/message.py"", line 301, in send
    return self.get_connection(fail_silently).send_messages([self])
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File ""/usr/local/lib/python3.12/site-packages/django/core/mail/backends/smtp.py"", line 136, in send_messages
    sent = self._send(message)
           ^^^^^^^^^^^^^^^^^^^
  File ""/usr/local/lib/python3.12/site-packages/django/core/mail/backends/smtp.py"", line 156, in _send
    from_email, recipients, message.as_bytes(linesep=""\r\n"")
                            ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File ""/usr/local/lib/python3.12/site-packages/django/core/mail/message.py"", line 148, in as_bytes
    g.flatten(self, unixfrom=unixfrom, linesep=linesep)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 117, in flatten
    self._write(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 182, in _write
    self._dispatch(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 219, in _dispatch
    meth(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 286, in _handle_multipart
    g.flatten(part, unixfrom=False, linesep=self._NL)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 117, in flatten
    self._write(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 182, in _write
    self._dispatch(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 219, in _dispatch
    meth(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 372, in _handle_message
    g.flatten(msg.get_payload(0), unixfrom=False, linesep=self._NL)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 117, in flatten
    self._write(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 182, in _write
    self._dispatch(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 219, in _dispatch
    meth(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 446, in _handle_text
    super(BytesGenerator,self)._handle_text(msg)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 263, in _handle_text
    self._write_lines(payload)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 156, in _write_lines
    self.write(line)
  File ""/usr/local/lib/python3.12/email/generator.py"", line 420, in write
    self._fp.write(s.encode('ascii', 'surrogateescape'))

                    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
 UnicodeEncodeError: 'ascii' codec can't encode characters in position 10-15: ordinal not in range(128)
}}}"	Bug	closed	Core (Mail)	5.1	Normal	fixed	compat32	Mike Edmunds	Ready for checkin	1	0	0	0	0	0