The crash happens on line 2015 of mail Gem, version 2.8.1:
def set_envelope_header
raw_string = raw_source.to_s
if match_data = raw_string.match(/\AFrom\s+([^:\s]#{Constants::TEXT}*)#{Constants::LAX_CRLF}/m)
To me it looks like the encoding
Content-Type: text/plain; charset=WINDOWS-1252
Content-Transfer-Encoding: 7bit
might be responsible along with a special apostrophe character in:
haven’t