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I'm trying to troubleshoot an SMTP issue. My credentials work fine via the OS X Mail client (and in other areas), so the credentials are definitely good. However, when I try to submit them via: openssl s_client -starttls smtp -crlf -connect smtp.mail.me.com:587, I get a 535 response (Failed Authentication).

I used Wireshark to watch both exchanges, and they look similar, although I haven't figured out how to decrypt the traffic so as to be able to see the Mail client's exchange in plaintext.

[Edit: I tried my gmail account using openssl, and it works fine, using AUTH PLAIN. Is there something weird about Apple's AUTH system?]

Here is the openssl exchange, anonymized where needed:

openssl s_client -starttls smtp -crlf -connect smtp.mail.me.com:587
CONNECTED(00000003)
depth=2 /C=US/O=VeriSign, Inc./OU=VeriSign Trust Network/OU=(c) 2006 VeriSign, Inc. - For authorized use only/CN=VeriSign Class 3 Public Primary Certification Authority - G5
verify error:num=20:unable to get local issuer certificate
verify return:0
---
Certificate chain
 0 s:/C=US/ST=California/L=Cupertino/O=Apple Inc./CN=*.mail.me.com
   i:/C=US/O=VeriSign, Inc./OU=VeriSign Trust Network/OU=Terms of use at https://www.verisign.com/rpa (c)10/CN=VeriSign Class 3 Secure Server CA - G3
 1 s:/C=US/O=VeriSign, Inc./OU=VeriSign Trust Network/OU=Terms of use at https://www.verisign.com/rpa (c)10/CN=VeriSign Class 3 Secure Server CA - G3
   i:/C=US/O=VeriSign, Inc./OU=VeriSign Trust Network/OU=(c) 2006 VeriSign, Inc. - For authorized use only/CN=VeriSign Class 3 Public Primary Certification Authority - G5
 2 s:/C=US/O=VeriSign, Inc./OU=VeriSign Trust Network/OU=(c) 2006 VeriSign, Inc. - For authorized use only/CN=VeriSign Class 3 Public Primary Certification Authority - G5
   i:/C=US/O=VeriSign, Inc./OU=Class 3 Public Primary Certification Authority
---
Server certificate
-----BEGIN CERTIFICATE-----
MIIFC......certificate characters....50bq4=
-----END CERTIFICATE-----
subject=/C=US/ST=California/L=Cupertino/O=Apple Inc./CN=*.mail.me.com
issuer=/C=US/O=VeriSign, Inc./OU=VeriSign Trust Network/OU=Terms of use at https://www.verisign.com/rpa (c)10/CN=VeriSign Class 3 Secure Server CA - G3
---
No client certificate CA names sent
---
SSL handshake has read 4717 bytes and written 491 bytes
---
New, TLSv1/SSLv3, Cipher is AES128-SHA
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol  : TLSv1
    Cipher    : AES128-SHA
    Session-ID: 15987251B4A0B361AC3690B88A2A972C57747B5CAD15B613D92F6CE97284789F
    Session-ID-ctx: 
    Master-Key: [long string here]
    Key-Arg   : None
    Start Time: 1417991368
    Timeout   : 300 (sec)
    Verify return code: 0 (ok)
---
250 SIZE 28311552
ehlo testing
250-st11p00mm-asmtp002.mac.com
250-8BITMIME
250-PIPELINING
250-CHUNKING
250-DSN
250-ENHANCEDSTATUSCODES
250-EXPN
250-HELP
250-XADR
250-XSTA
250-XCIR
250-XGEN
250-XLOOP 2CE0B8913D00E705D3D542BA5DF0FCE8
250-AUTH PLAIN LOGIN ATOKEN
250-AUTH=LOGIN PLAIN
250-NO-SOLICITING
250 SIZE 28311552
AUTH PLAIN
334 
[base-64 credentials entered here]
535 5.7.8 Bad username or password (Authentication failed).

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