This is super weird, you're having an identical issue to me, including from a sendgrid address:

ERROR: UID 126179 (<zf3lf1bgtw-ct-y9a15wlquq3bukrddphg-173.82.166...@ismtpd0003p1iad1.sendgrid.net>) has defects preventing it from being processed! UnicodeEncodeError: 'ascii' codec can't encode characters in position 434-435: ordinal not in range(128)

I've been meaning to post on stackoverflow or here about it but just haven't gotten around to it

It prevents me from keeping offlineimap running continously because it causes a crash.

I also wasn't able to find the offending email on my gmail server anywhere, at least not using gmail's search tools (or other applications), because if I could I'd just delete it and move on.

Jonathan Whitehead <[email protected]> writes:

I'm running imap in a docker container (maxkratz/onlineimap), after trying repeatedly to run it in bare debian. I'm backing up from
Gmail.  In the container, offlineimap -V shows:

offlineimap v8.0.0, imaplib2 v3.05, Python v3.10.6, OpenSSL 3.0.2 15 Mar 2022

The docker container gets me further, but in both cases, offlineimap eventually errors and closes after hitting 5-10 encoding errors, such
as:

ERROR: UID 140848 (<zf3lf1bgtw-ct-y9a5zzl3q6mxoddphg-212.129.51...@ismtpd0003p1iad1.sendgrid.net>) has defects preventing it from being processed!

UnicodeEncodeError: 'ascii' codec can't encode characters in position 434-435: ordinal not in range(128)

Traceback:

File "/usr/share/offlineimap3/offlineimap/folder/Base.py", line 810, in copymessageto

    message = self.getmessage(uid)

File "/usr/share/offlineimap3/offlineimap/folder/Gmail.py", line 69, in getmessage

    data = self._fetch_from_imap(str(uid), self.retrycount)

File "/usr/share/offlineimap3/offlineimap/folder/IMAP.py", line 930, in _fetch_from_imap

    raise OfflineImapError(

This seems to be related to UTF-8 encoding somehow. My next step would be to look at these message (or figure out a fix). But how do I determine which message is causing the failure? UID 140848 doesn't appear in my maildir yet, and Gmail does not see the sendgrid address when I search.

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- http://offlineimap.org

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