Hi,

IMO, this problem has nothing to do with stunnel.

There are plenty of issues reported on the web, most of them related to Outlook.

Does it happen with all email addresses or a specific one ?

Flo

On Tue, May 15, 2018 at 9:56 AM, Alix Janeth Jerez <alixj@hotmail.com> wrote:
Hi

I am using lastest stunnel version. 

When i try to send an email, i get:

"error permanente de SMTP: 503 Bad sequence of commands".

This is the trace generated when I try to send an email.

 2018.05.14 12:59:08 LOG5[main]: Reading configuration from file stunnel.conf
 2018.05.14 12:59:08 LOG5[main]: UTF-8 byte order mark not detected
 2018.05.14 12:59:08 LOG5[main]: FIPS mode disabled
 2018.05.14 12:59:08 LOG5[main]: Configuration successful
 2018.05.14 12:59:08 LOG7[main]: Binding service [pseudo-ssmtp]
 2018.05.14 12:59:08 LOG7[main]: Listening file descriptor created (FD=568)
 2018.05.14 12:59:08 LOG7[main]: Option SO_EXCLUSIVEADDRUSE set on accept socket
 2018.05.14 12:59:08 LOG7[main]: Service [pseudo-ssmtp] (FD=568) bound to 172.31.41.84:116
 2018.05.14 12:59:08 LOG7[main]: Signal pipe is empty
 2018.05.14 12:59:22 LOG7[main]: Found 1 ready file descriptor(s)
 2018.05.14 12:59:22 LOG7[main]: FD=324 ifds=r-x ofds=r--
 2018.05.14 12:59:22 LOG7[main]: Dispatching signals from the signal pipe
 2018.05.14 12:59:22 LOG7[main]: Processing SIGNAL_RELOAD_CONFIG
 2018.05.14 12:59:22 LOG7[main]: Running on Windows 6.1
 2018.05.14 12:59:22 LOG5[main]: Reading configuration from file stunnel.conf
 2018.05.14 12:59:22 LOG5[main]: UTF-8 byte order mark not detected
 2018.05.14 12:59:22 LOG5[main]: FIPS mode disabled
 2018.05.14 12:59:22 LOG7[main]: Compression disabled
 2018.05.14 12:59:22 LOG7[main]: Snagged 64 random bytes from C:/.rnd
 2018.05.14 12:59:22 LOG7[main]: Wrote 1024 new random bytes to C:/.rnd
 2018.05.14 12:59:22 LOG7[main]: PRNG seeded successfully
 2018.05.14 12:59:22 LOG6[main]: Initializing service [pseudo-ssmtp]
 2018.05.14 12:59:22 LOG7[main]: Ciphers: HIGH:!DH:!aNULL:!SSLv2
 2018.05.14 12:59:22 LOG7[main]: TLS options: 0x03000004 (+0x03000000, 0x00000000)
 2018.05.14 12:59:22 LOG6[main]: Loading certificate from file: stunnel.pem
 2018.05.14 12:59:22 LOG6[main]: Certificate loaded from file: stunnel.pem
 2018.05.14 12:59:22 LOG6[main]: Loading private key from file: stunnel.pem
 2018.05.14 12:59:22 LOG6[main]: Private key loaded from file: stunnel.pem
 2018.05.14 12:59:22 LOG7[main]: Private key check succeeded
 2018.05.14 12:59:22 LOG5[main]: Configuration successful
 2018.05.14 12:59:22 LOG7[main]: Unbinding service [pseudo-ssmtp]
 2018.05.14 12:59:22 LOG7[main]: Service [pseudo-ssmtp] closed (FD=568)
 2018.05.14 12:59:22 LOG7[main]: Service [pseudo-ssmtp] closed
 2018.05.14 12:59:22 LOG7[main]: Binding service [pseudo-ssmtp]
 2018.05.14 12:59:22 LOG7[main]: Listening file descriptor created (FD=568)
 2018.05.14 12:59:22 LOG7[main]: Option SO_EXCLUSIVEADDRUSE set on accept socket
 2018.05.14 12:59:22 LOG7[main]: Service [pseudo-ssmtp] (FD=568) bound to 172.31.41.84:116
 2018.05.14 12:59:22 LOG7[main]: Signal pipe is empty
 2018.05.14 12:59:34 LOG7[main]: Found 1 ready file descriptor(s)
 2018.05.14 12:59:34 LOG7[main]: FD=324 ifds=r-x ofds=---
 2018.05.14 12:59:34 LOG7[main]: Service [pseudo-ssmtp] accepted (FD=584) from 172.31.41.84:53557
 2018.05.14 12:59:34 LOG7[main]: Creating a new thread
 2018.05.14 12:59:34 LOG7[main]: New thread created
 2018.05.14 12:59:34 LOG7[37]: Service [pseudo-ssmtp] started
 2018.05.14 12:59:34 LOG7[37]: Option TCP_NODELAY set on local socket
 2018.05.14 12:59:34 LOG5[37]: Service [pseudo-ssmtp] accepted connection from 172.31.41.84:53557
 2018.05.14 12:59:34 LOG6[37]: failover: round-robin, starting at entry #1
 2018.05.14 12:59:34 LOG6[37]: s_connect: connecting 212.227.15.158:465
 2018.05.14 12:59:34 LOG7[37]: s_connect: s_poll_wait 212.227.15.158:465: waiting 10 seconds
2018.05.14 12:59:34 LOG5[37]: s_connect: connected 212.227.15.158:465
2018.05.14 12:59:34 LOG5[37]: Service [pseudo-ssmtp] connected remote server from 172.31.41.84:53558
2018.05.14 12:59:34 LOG7[37]: Option TCP_NODELAY set on remote socket
2018.05.14 12:59:34 LOG7[37]: Remote descriptor (FD=552) initialized
2018.05.14 12:59:34 LOG6[37]: SNI: sending servername: smtp.1and1.es
2018.05.14 12:59:34 LOG6[37]: Peer certificate required
2018.05.14 12:59:34 LOG7[37]: TLS state (connect): before/connect initialization
2018.05.14 12:59:34 LOG7[37]: TLS state (connect): SSLv2/v3 write client hello A
2018.05.14 12:59:34 LOG7[37]: TLS state (connect): SSLv3 read server hello A
2018.05.14 12:59:34 LOG7[37]: Verification started at depth=2: C=US, O="thawte, Inc.", OU=Certification Services Division, OU="(c) 2006 thawte, Inc. - For authorized use only", CN=thawte Primary Root CA
2018.05.14 12:59:34 LOG7[37]: CERT: Pre-verification succeeded
2018.05.14 12:59:34 LOG7[37]: OCSP: Ignoring root certificate
2018.05.14 12:59:34 LOG6[37]: Certificate accepted at depth=2: C=US, O="thawte, Inc.", OU=Certification Services Division, OU="(c) 2006 thawte, Inc. - For authorized use only", CN=thawte Primary Root CA
2018.05.14 12:59:34 LOG7[37]: Verification started at depth=1: C=US, O="thawte, Inc.", CN=thawte SSL CA - G2
2018.05.14 12:59:34 LOG7[37]: CERT: Pre-verification succeeded
2018.05.14 12:59:34 LOG5[37]: OCSP: Connecting the AIA responder "http://t2.symcb.com"
2018.05.14 12:59:34 LOG6[37]: s_connect: connecting 23.5.251.27:80
2018.05.14 12:59:34 LOG7[37]: s_connect: s_poll_wait 23.5.251.27:80: waiting 10 seconds
2018.05.14 12:59:34 LOG5[37]: s_connect: connected 23.5.251.27:80
2018.05.14 12:59:34 LOG7[37]: OCSP: Connected t2.symcb.com:80
2018.05.14 12:59:34 LOG7[37]: OCSP: Response received
2018.05.14 12:59:34 LOG6[37]: OCSP: Status: good
2018.05.14 12:59:34 LOG6[37]: OCSP: This update: May 13 18:15:02 2018 GMT
2018.05.14 12:59:34 LOG6[37]: OCSP: Next update: May 20 18:15:02 2018 GMT
2018.05.14 12:59:34 LOG5[37]: OCSP: Certificate accepted
2018.05.14 12:59:34 LOG6[37]: Certificate accepted at depth=1: C=US, O="thawte, Inc.", CN=thawte SSL CA - G2
2018.05.14 12:59:34 LOG7[37]: Verification started at depth=0: C=DE, ST=Rheinland-Pfalz, L=Montabaur, O=1&1 Internet SE, CN=smtp.1and1.es
2018.05.14 12:59:34 LOG7[37]: CERT: Pre-verification succeeded
2018.05.14 12:59:34 LOG6[37]: CERT: Host name "smtp.1and1.es" matched with "smtp.1and1.es"
2018.05.14 12:59:34 LOG5[37]: OCSP: Connecting the AIA responder "http://tj.symcd.com"
2018.05.14 12:59:34 LOG6[37]: s_connect: connecting 23.5.251.27:80
2018.05.14 12:59:34 LOG7[37]: s_connect: s_poll_wait 23.5.251.27:80: waiting 10 seconds
2018.05.14 12:59:35 LOG5[37]: s_connect: connected 23.5.251.27:80
2018.05.14 12:59:35 LOG7[37]: OCSP: Connected tj.symcd.com:80
2018.05.14 12:59:35 LOG7[37]: OCSP: Response received
2018.05.14 12:59:35 LOG6[37]: OCSP: Status: good
2018.05.14 12:59:35 LOG6[37]: OCSP: This update: May 14 01:38:59 2018 GMT
2018.05.14 12:59:35 LOG6[37]: OCSP: Next update: May 21 01:38:59 2018 GMT
2018.05.14 12:59:35 LOG5[37]: OCSP: Certificate accepted
2018.05.14 12:59:35 LOG5[37]: Certificate accepted at depth=0: C=DE, ST=Rheinland-Pfalz, L=Montabaur, O=1&1 Internet SE, CN=smtp.1and1.es
2018.05.14 12:59:35 LOG7[37]: TLS state (connect): SSLv3 read server certificate A
2018.05.14 12:59:35 LOG7[37]: TLS state (connect): SSLv3 read server key exchange A
2018.05.14 12:59:35 LOG6[37]: Client certificate not requested
2018.05.14 12:59:35 LOG7[37]: TLS state (connect): SSLv3 read server done A
2018.05.14 12:59:35 LOG7[37]: TLS state (connect): SSLv3 write client key exchange A
2018.05.14 12:59:35 LOG7[37]: TLS state (connect): SSLv3 write change cipher spec A
2018.05.14 12:59:35 LOG7[37]: TLS state (connect): SSLv3 write finished A
2018.05.14 12:59:35 LOG7[37]: TLS state (connect): SSLv3 flush data
2018.05.14 12:59:35 LOG7[37]: TLS state (connect): SSLv3 read finished A
2018.05.14 12:59:35 LOG7[37]:      1 client connect(s) requested
2018.05.14 12:59:35 LOG7[37]:      1 client connect(s) succeeded
2018.05.14 12:59:35 LOG7[37]:      0 client renegotiation(s) requested
2018.05.14 12:59:35 LOG7[37]:      0 session reuse(s)
2018.05.14 12:59:35 LOG6[37]: TLS connected: new session negotiated
2018.05.14 12:59:35 LOG7[37]: Peer certificate was cached (5543 bytes)
2018.05.14 12:59:35 LOG6[37]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)
2018.05.14 12:59:35 LOG7[37]: Compression: null, expansion: null
2018.05.14 12:59:53 LOG3[36]: transfer: s_poll_wait: TIMEOUTclose exceeded: closing
2018.05.14 12:59:53 LOG5[36]: Connection closed: 15 byte(s) sent to TLS, 166 byte(s) sent to socket

I can't find the error.

Thanks in advance for your help.


Best regards,

Alix

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