[stunnel-users] Unable to authenticate with Outlook.com servers (SMTP)

Michal Trojnara Michal.Trojnara at mirt.net
Thu Oct 15 17:12:54 CEST 2015 

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Hi Aerowinder,

The protocolUsername and protocolPassword options are currently only
supported with the "connect" protocol.  There are plans to also
support them in the "smtp" protocol, but this feature is not
implemented yet.

Best regards,
	Mike

On 15.10.2015 17:03, Aerowinder wrote:
> Greetings,
> 
> Running stunnel 5.25 latest beta (2015-10-15), but also had the
> same issues on 5.24 final.
> 
> My config file looks like this:
> 
> debug = debug output = xxxxx client = yes cert = stunnel.pem
> 
> [outlook-smtp] accept = 127.0.0.1:25 connect =
> smtp-mail.outlook.com:587 protocol = smtp ;protocolUsername = xxxx 
> ;protocolPassword = xxxx CAfile = ca-certs.pem checkHost =
> smtp-mail.outlook.com OCSPaia = yes verify = 2
> 
> 
> I am testing functionality to make sure that I am able to send
> mail with my Outlook.com address. I currently have User/Pass field 
> commented out, but I've tried with them not commented out, and the 
> actual values instead of "xxxx" (the app I'm using has fields for 
> username and password).
> 
> My log:
> 
> 2015.10.15 11:01:24 LOG7[cron]: Cron started 2015.10.15 11:01:24
> LOG7[main]: No limit detected for the number of clients 2015.10.15
> 11:01:24 LOG5[main]: stunnel 5.25 on x86-pc-msvc-1500 platform 
> 2015.10.15 11:01:24 LOG5[main]: Compiled/running with OpenSSL 
> 1.0.2d-fips 9 Jul 2015 2015.10.15 11:01:24 LOG5[main]:
> Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI 
> 2015.10.15 11:01:24 LOG7[main]: errno: (*_errno()) 2015.10.15
> 11:01:24 LOG7[ui]: GUI message loop initialized 2015.10.15 11:01:24
> LOG5[main]: Reading configuration from file stunnel.conf 2015.10.15
> 11:01:24 LOG5[main]: UTF-8 byte order mark detected 2015.10.15
> 11:01:24 LOG5[main]: FIPS mode disabled 2015.10.15 11:01:24
> LOG7[main]: Compression disabled 2015.10.15 11:01:24 LOG7[main]:
> PRNG seeded successfully 2015.10.15 11:01:24 LOG6[main]:
> Initializing service [outlook-smtp] 2015.10.15 11:01:24 LOG6[main]:
> Loading certificate from file: stunnel.pem 2015.10.15 11:01:24
> LOG6[main]: Loading key from file: stunnel.pem 2015.10.15 11:01:24
> LOG7[main]: Private key check succeeded 2015.10.15 11:01:24
> LOG7[main]: SSL options: 0x03000004 (+0x03000000, -0x00000000) 
> 2015.10.15 11:01:24 LOG5[main]: Configuration successful 2015.10.15
> 11:01:24 LOG7[main]: Listening file descriptor created (FD=652) 
> 2015.10.15 11:01:24 LOG7[main]: Service [outlook-smtp] (FD=652)
> bound to 127.0.0.1:25 2015.10.15 11:01:31 LOG7[main]: Found 1 ready
> file descriptor(s) 2015.10.15 11:01:31 LOG7[main]: FD=408 ifds=r-x
> ofds=--- 2015.10.15 11:01:31 LOG7[main]: Service [outlook-smtp]
> accepted (FD=692) from 127.0.0.1:58065 2015.10.15 11:01:31
> LOG7[main]: Creating a new thread 2015.10.15 11:01:31 LOG7[main]:
> New thread created 2015.10.15 11:01:31 LOG7[0]: Service
> [outlook-smtp] started 2015.10.15 11:01:31 LOG5[0]: Service
> [outlook-smtp] accepted connection from 127.0.0.1:58065 2015.10.15
> 11:01:31 LOG6[0]: s_connect: connecting 65.55.176.126:587 
> 2015.10.15 11:01:31 LOG7[0]: s_connect: s_poll_wait
> 65.55.176.126:587: waiting 10 seconds 2015.10.15 11:01:31 LOG5[0]:
> s_connect: connected 65.55.176.126:587 2015.10.15 11:01:31 LOG5[0]:
> Service [outlook-smtp] connected remote server from
> 172.26.1.51:58066 2015.10.15 11:01:31 LOG7[0]: Remote descriptor
> (FD=704) initialized 2015.10.15 11:01:31 LOG7[0]:  <- 220
> BLU436-SMTP245.smtp.hotmail.com Microsoft ESMTP MAIL Service,
> Version: 8.0.9200.16384 ready at  Thu, 15 Oct 2015 08:01:34 -0700 
> 2015.10.15 11:01:31 LOG7[0]:  -> 220
> BLU436-SMTP245.smtp.hotmail.com Microsoft ESMTP MAIL Service,
> Version: 8.0.9200.16384 ready at  Thu, 15 Oct 2015 08:01:34 -0700 
> 2015.10.15 11:01:31 LOG7[0]:  -> EHLO localhost 2015.10.15 11:01:31
> LOG7[0]:  <- 250-BLU436-SMTP245.smtp.hotmail.com Hello
> [70.90.151.129] 2015.10.15 11:01:31 LOG7[0]:  <- 250-TURN 
> 2015.10.15 11:01:31 LOG7[0]:  <- 250-SIZE 41943040 2015.10.15
> 11:01:31 LOG7[0]:  <- 250-ETRN 2015.10.15 11:01:31 LOG7[0]:  <-
> 250-PIPELINING 2015.10.15 11:01:31 LOG7[0]:  <- 250-DSN 2015.10.15
> 11:01:31 LOG7[0]:  <- 250-ENHANCEDSTATUSCODES 2015.10.15 11:01:31
> LOG7[0]:  <- 250-8bitmime 2015.10.15 11:01:31 LOG7[0]:  <-
> 250-BINARYMIME 2015.10.15 11:01:31 LOG7[0]:  <- 250-CHUNKING 
> 2015.10.15 11:01:31 LOG7[0]:  <- 250-VRFY 2015.10.15 11:01:31
> LOG7[0]:  <- 250-TLS 2015.10.15 11:01:31 LOG7[0]:  <- 250-STARTTLS 
> 2015.10.15 11:01:31 LOG7[0]:  <- 250 OK 2015.10.15 11:01:31
> LOG7[0]:  -> STARTTLS 2015.10.15 11:01:31 LOG7[0]:  <- 220 2.0.0
> SMTP server ready 2015.10.15 11:01:31 LOG6[0]: SNI: sending
> servername: smtp-mail.outlook.com 2015.10.15 11:01:31 LOG7[0]: SSL
> state (connect): before/connect initialization 2015.10.15 11:01:31
> LOG7[0]: SSL state (connect): SSLv2/v3 write client hello A 
> 2015.10.15 11:01:31 LOG7[0]: SSL state (connect): SSLv3 read server
> hello A 2015.10.15 11:01:31 LOG7[0]: Verification started at
> depth=2: C=BE, O=GlobalSign nv-sa, OU=Root CA, CN=GlobalSign Root
> CA 2015.10.15 11:01:31 LOG7[0]: CERT: Pre-verification succeeded 
> 2015.10.15 11:01:31 LOG7[0]: OCSP: Ignoring root certificate 
> 2015.10.15 11:01:31 LOG6[0]: Certificate accepted at depth=2:
> C=BE, O=GlobalSign nv-sa, OU=Root CA, CN=GlobalSign Root CA 
> 2015.10.15 11:01:31 LOG7[0]: Verification started at depth=1:
> C=BE, O=GlobalSign nv-sa, CN=GlobalSign Organization Validation CA
> - G2 2015.10.15 11:01:31 LOG7[0]: CERT: Pre-verification succeeded 
> 2015.10.15 11:01:31 LOG5[0]: OCSP: Connecting the AIA responder 
> "http://ocsp.globalsign.com/rootr1" 2015.10.15 11:01:31 LOG6[0]:
> s_connect: connecting 108.162.232.204:80 2015.10.15 11:01:31
> LOG7[0]: s_connect: s_poll_wait 108.162.232.204:80: waiting 10
> seconds 2015.10.15 11:01:31 LOG5[0]: s_connect: connected
> 108.162.232.204:80 2015.10.15 11:01:31 LOG7[0]: OCSP: Connected
> ocsp.globalsign.com:80 2015.10.15 11:01:31 LOG7[0]: OCSP: Response
> received 2015.10.15 11:01:31 LOG6[0]: OCSP: Status: good 2015.10.15
> 11:01:31 LOG6[0]: OCSP: This update: Oct 15 10:27:35 2015 GMT 
> 2015.10.15 11:01:31 LOG6[0]: OCSP: Next update: Oct 19 10:27:35
> 2015 GMT 2015.10.15 11:01:31 LOG5[0]: OCSP: Certificate accepted 
> 2015.10.15 11:01:31 LOG6[0]: Certificate accepted at depth=1:
> C=BE, O=GlobalSign nv-sa, CN=GlobalSign Organization Validation CA
> - G2 2015.10.15 11:01:31 LOG7[0]: Verification started at depth=0:
> C=US, ST=Washington, L=Redmond, O=Microsoft Corporation,
> CN=*.hotmail.com 2015.10.15 11:01:31 LOG7[0]: CERT:
> Pre-verification succeeded 2015.10.15 11:01:31 LOG6[0]: CERT: Host
> name "smtp-mail.outlook.com" matched with "*.outlook.com" 
> 2015.10.15 11:01:31 LOG5[0]: OCSP: Connecting the AIA responder 
> "http://ocsp2.globalsign.com/gsorganizationvalg2" 2015.10.15
> 11:01:31 LOG6[0]: s_connect: connecting 108.162.232.196:80 
> 2015.10.15 11:01:31 LOG7[0]: s_connect: s_poll_wait 
> 108.162.232.196:80: waiting 10 seconds 2015.10.15 11:01:31 LOG5[0]:
> s_connect: connected 108.162.232.196:80 2015.10.15 11:01:31
> LOG7[0]: OCSP: Connected ocsp2.globalsign.com:80 2015.10.15
> 11:01:31 LOG7[0]: OCSP: Response received 2015.10.15 11:01:31
> LOG6[0]: OCSP: Status: good 2015.10.15 11:01:31 LOG6[0]: OCSP: This
> update: Oct 15 08:26:15 2015 GMT 2015.10.15 11:01:31 LOG6[0]: OCSP:
> Next update: Oct 16 08:26:15 2015 GMT 2015.10.15 11:01:31 LOG5[0]:
> OCSP: Certificate accepted 2015.10.15 11:01:31 LOG5[0]: Certificate
> accepted at depth=0: C=US, ST=Washington, L=Redmond, O=Microsoft
> Corporation, CN=*.hotmail.com 2015.10.15 11:01:31 LOG7[0]: SSL
> state (connect): SSLv3 read server certificate A 2015.10.15
> 11:01:31 LOG7[0]: SSL state (connect): SSLv3 read server key
> exchange A 2015.10.15 11:01:31 LOG7[0]: SSL state (connect): SSLv3
> read server done A 2015.10.15 11:01:31 LOG7[0]: SSL state
> (connect): SSLv3 write client key exchange A 2015.10.15 11:01:31
> LOG7[0]: SSL state (connect): SSLv3 write change cipher spec A 
> 2015.10.15 11:01:31 LOG7[0]: SSL state (connect): SSLv3 write
> finished A 2015.10.15 11:01:31 LOG7[0]: SSL state (connect): SSLv3
> flush data 2015.10.15 11:01:31 LOG7[0]: SSL state (connect): SSLv3
> read finished A 2015.10.15 11:01:31 LOG7[0]:      1 client
> connect(s) requested 2015.10.15 11:01:31 LOG7[0]:      1 client
> connect(s) succeeded 2015.10.15 11:01:31 LOG7[0]:      0 client
> renegotiation(s) requested 2015.10.15 11:01:31 LOG7[0]:      0
> session reuse(s) 2015.10.15 11:01:31 LOG6[0]: SSL connected: new
> session negotiated 2015.10.15 11:01:31 LOG7[0]: Peer certificate
> was cached (3461 bytes) 2015.10.15 11:01:31 LOG6[0]: Negotiated
> TLSv1.2 ciphersuite ECDHE-RSA-AES256-SHA384 (256-bit encryption) 
> 2015.10.15 11:01:31 LOG7[0]: Compression: null, expansion: null 
> 2015.10.15 11:01:31 LOG6[0]: SSL socket closed (SSL_read) 
> 2015.10.15 11:01:31 LOG7[0]: Sent socket write shutdown 2015.10.15
> 11:01:31 LOG5[0]: Connection closed: 139 byte(s) sent to SSL, 351
> byte(s) sent to socket 2015.10.15 11:01:31 LOG7[0]: Remote
> descriptor (FD=704) closed 2015.10.15 11:01:31 LOG7[0]: Local
> descriptor (FD=692) closed 2015.10.15 11:01:31 LOG7[0]: Service
> [outlook-smtp] finished (0 left)
> 
> 
> 
> I don't see any errors in the log, but Outlook is reporting an 
> incorrect password on the security section of my Microsoft
> Account. More specifically, I'm seeing error 5.7.3: Requested
> action aborted, user not authenticated," I know the password works
> because I set it up as an account in Outlook 2010 and tested
> sending the email. It works great. I am using 2FA with an
> app-specific password. But I have also tried without 2FA. I am 100%
> certain the account name xxxx at outlook.com and the password are
> correct. As far as the config file goes, I've tried just about
> everything I could find on Google. Nothing works, always the same
> error message.
> 
> I also experienced similar failures with Gmail.
> 
> Any ideas? _______________________________________________ 
> stunnel-users mailing list stunnel-users at stunnel.org 
> https://www.stunnel.org/cgi-bin/mailman/listinfo/stunnel-users
> 
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