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Bug #1806: Figure out why wincent.dev SMTP is stuck at "RENEGOTIATING" when outside of office

Kind bug
Product wincent.dev
When Created , updated
Status closed
Reporter Greg Hurrell
Tags no tags

Description

Other email accounts hosted on the same server work fine: 

$ openssl s_client -connect wincent.dev:465
...
EHLO 127.0.0.1
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-AUTH DIGEST-MD5 CRAM-MD5 LOGIN PLAIN
250-DELIVERBY
250 HELP
AUTH LOGIN
334 foo
username_digest
334 bar
password_digest
RENEGOTIATING
^C

Other accounts on same server authenticate fine:

AUTH LOGIN
334 foo
username_digest
334 bar
password_digest
235 2.0.0 OK Authenticated
QUIT
DONE

Seeing a similar thing with my Gmail account. Works at the office, fails outside the office: 

535-5.7.1 Username and Password not accepted. Learn more at                   
535 5.7.1 http://mail.google.com/support/bin/answer.py?answer=14257 i3sm1879026pbb.26

(Well, technically speaking, I can send mail via Mail.app at the office, but when using the openssl s_client -connect smtp.gmail.com:465 trick, I fail...

Comments

  1. Greg Hurrell

    Answer found here. The renegotiation is triggered because my the Base 64 representation of my password just happens to start with a capital R, meaning that it will trigger renegotiation as soon as I enter it.

    This can be suppressed with the -ign_eof switch. Also from that link, I see that the -crlf is a good idea to ensure that the end-of-message marker is correctly processed (the RFC expects \r\n.\r\n to indicate the end of the message submission.

    No idea why this only recently became a problem in Mail.app. Never noticed it before.

    Easiest work around for now seems to be to just change my password.

  2. Greg Hurrell

    Ok, I've changed my password and tested sending mail from the web interface and over the command line and both work but Mail.app is still being stubborn. Going to reboot just in case it's hanging on to some stale authentication info somewhere (although no idea where that might be, seeing as it should be in the keychain and the keychain is up to date).

  3. Greg Hurrell

    Nope, still not working, so something bizarre going on.

  4. Greg Hurrell

    Just tested with Thunderbird and it works fine for all 3 accounts, so this is buggy behavior in Mail.app.

  5. Greg Hurrell

    Ok, after deleting and re-adding all the server configs, things seem to be working in Mail.app again (all three servers).

  6. Greg Hurrell

    Status changed:

    • From: new
    • To: closed
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