Running the test case I ran into the same error Christian did, mentioned
in comment #8, but after hacking on the testcase a bit (I don't know
Ruby, but studying the code in /usr/lib/ruby/2.5.0/net/smtp.rb gave
enough clues) I was able to reproduce:

$ ./testcase-ruby-ssl.rb 
1
2
3
4
5
6
6.1Traceback (most recent call last):
        26: from ./testcase-ruby-ssl.rb:46:in `<main>'
        25: from /usr/lib/ruby/2.5.0/net/smtp.rb:519:in `start'
        24: from ./testcase-ruby-ssl.rb:48:in `block in <main>'
        23: from /usr/lib/ruby/2.5.0/net/smtp.rb:659:in `send_message'
        22: from /usr/lib/ruby/2.5.0/net/smtp.rb:854:in `rcptto_list'
        21: from /usr/lib/ruby/2.5.0/net/smtp.rb:659:in `block in send_message'
        20: from /usr/lib/ruby/2.5.0/net/smtp.rb:898:in `data'
        19: from /usr/lib/ruby/2.5.0/net/smtp.rb:960:in `critical'
        18: from /usr/lib/ruby/2.5.0/net/smtp.rb:904:in `block in data'
        17: from /usr/lib/ruby/2.5.0/net/protocol.rb:304:in `write_message'
        16: from /usr/lib/ruby/2.5.0/net/protocol.rb:224:in `writing'
        15: from /usr/lib/ruby/2.5.0/net/protocol.rb:305:in `block in 
write_message'
        14: from /usr/lib/ruby/2.5.0/net/protocol.rb:339:in 
`using_each_crlf_line'
        13: from /usr/lib/ruby/2.5.0/net/protocol.rb:306:in `block (2 levels) 
in write_message'
        12: from /usr/lib/ruby/2.5.0/net/protocol.rb:291:in `write_message_0'
        11: from /usr/lib/ruby/2.5.0/net/protocol.rb:350:in `each_crlf_line'
        10: from /usr/lib/ruby/2.5.0/net/protocol.rb:360:in `buffer_filling'
         9: from /usr/lib/ruby/2.5.0/net/protocol.rb:360:in `step'
         8: from /usr/lib/ruby/2.5.0/net/protocol.rb:362:in `block in 
buffer_filling'
         7: from /usr/lib/ruby/2.5.0/net/protocol.rb:352:in `block in 
each_crlf_line'
         6: from /usr/lib/ruby/2.5.0/net/protocol.rb:292:in `block in 
write_message_0'
         5: from /usr/lib/ruby/2.5.0/net/protocol.rb:233:in `write0'
         4: from /usr/lib/ruby/2.5.0/openssl/buffering.rb:338:in `write'
         3: from /usr/lib/ruby/2.5.0/openssl/buffering.rb:338:in `inject'
         2: from /usr/lib/ruby/2.5.0/openssl/buffering.rb:338:in `each'
         1: from /usr/lib/ruby/2.5.0/openssl/buffering.rb:339:in `block in 
write'
/usr/lib/ruby/2.5.0/openssl/buffering.rb:316:in `do_write': incompatible 
character encodings: ASCII-8BIT and UTF-8 (Encoding::CompatibilityError)

At least, this seems to match the original reported error string, so
presumably it's a positive.

Next I'll start patch testing.

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https://bugs.launchpad.net/bugs/1835968

Title:
  Regression in backported patch for openssl 1.1

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