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failed email delivery (TLS connections)

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richyd

MIS
Jan 4, 2002
82
GB
Hi, I'm experiencing a weird problem which is preventing emails from a particular client. The client mentions they're able to send emails to other companys apart from ours so there must be a problem with the connection between these two companies.

Below are a couple of errors bouncing back to the senders -


----- The following addresses had permanent fatal errors ----- <richard.davis@xxxxxxx.co.uk>

----- Transcript of session follows ----- <richard.davis@xxxxxxx.co.uk>... Deferred: Bad file number Message could not be delivered for 3 days Message will be deleted from queue ========



And



Your document: mail test
was not delivered to: test.user@xxxxxxx.co.uk
because: 451 Remote connection lost - psmtp




One thing I do know is that the company who sends the email send using TLS connections. However our ISP tells me we're able to recieve TLS emails.

Further troubleshooting has revealed that our email systems do not seem to allow the Postini servers which deliver outbound mail from the client to connect to our email servers via TLS, which produces the error.

The sender said they have run some tests and these are the results -

I sent a mail to the address you listed, In the Postini outbound routed case the message failed on STARTTLS, on the direct send the STARTTLS failed and the server reverted back to standard SMTP transmission. By the way GMAIL and Yahoo probably don't send TLS which could explain why they work.

Burt

# /usr/lib/sendmail -v -q Ij8NKAQS2029739

Running /var/spool/mqueue/q18/df/j8NKAQS2029739 (sequence 1 of 1)

<test.user@mass-systems.co.uk>... Connecting to outbounds6.obsmtp.com. via relay...

220 Postini ESMTP 3 r6_3_2c0 ready. CA Business and Professions Code Section 17538.45 forbids use of this system for unsolicited electronic mail advertisements.

>>> EHLO rtpsfimr001.glaxo.com

250-Postini says hello back

250-STARTTLS

250-8BITMIME

250 HELP

>>> STARTTLS

220 Go ahead

>>> EHLO rtpsfimr001.glaxo.com

250-Postini says hello back

250-8BITMIME

250 HELP

>>> MAIL From:<burt.a.marshall@gsk.com>

250 Ok

>>> RCPT To:<test.user@mass-systems.co.uk>

451 Remote connection is failed in STARTTLS - psmtp

<test.user@mass-systems.co.uk>... Deferred: 451 Remote connection is failed in STARTTLS - psmtp

>>> RSET

250 Ok

Closing connection to outbounds6.obsmtp.com.

>>> QUIT

221 Catch you later

I changed mailertable

and retried message

# /usr/lib/sendmail -v -q Ij8NKAQS2029739

Running /var/spool/mqueue/q18/df/j8NKAQS2029739 (sequence 1 of 1)

<test.user@mass-systems.co.uk>... Connecting to mail.mass-systems.co.uk. via esmtp...

220 denzil.priv.mass-systems.co.uk Microsoft ESMTP MAIL Service,
Version: 5.0.2195.6713 ready at Fri, 23 Sep 2005 21:24:09 +0100

>>> EHLO rtpsfimr001.glaxo.com

250-denzil.priv.mass-systems.co.uk Hello [192.58.204.11]

250-TURN

250-ATRN

250-SIZE

250-ETRN

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-8bitmime

250-BINARYMIME

250-CHUNKING

250-VRFY

250-TLS

250-STARTTLS

250-X-EXPS GSSAPI NTLM LOGIN

250-X-EXPS=LOGIN

250-AUTH GSSAPI NTLM LOGIN

250-AUTH=LOGIN

250-X-LINK2STATE

250-XEXCH50

250 OK

>>> STARTTLS

220 2.0.0 SMTP server ready

<test.user@mass-systems.co.uk>... Connecting to dsl-relay1.gxn.net. via esmtp...

<test.user@mass-systems.co.uk>... Closing connection to mail.mass-systems.co.uk.

Here are the log entries, the STARTTLS is failing

Sep 23 16:19:01 rtpsfimr001 sendmail[2591]: [ID 801593 mail.error]
j8NKAQS2029739: STARTTLS=client, error: connect fail

ed=-1, SSL_error=5, timedout=0, errno=131

Sep 23 16:19:01 rtpsfimr001 sendmail[2591]: [ID 702911 mail.notice] ruleset=tls_server, arg1=SOFTWARE, relay=mail.mass-

systems.co.uk, reject=403 4.7.0 TLS handshake failed.

Sep 23 16:19:02 rtpsfimr001 sendmail[2591]: [ID 801593 mail.info]
j8NKAQS2029739: to=<test.user@mass-systems.co.uk>, de

lay=00:08:36, xdelay=00:00:01, mailer=esmtp, pri=301971, relay=dsl-relay1.gxn.net. [195.147.9.38], dsn=2.0.0, stat=Sent

(OK id=1EIv1C-0003kA-00)Closing connection to mail.mass-systems.co.uk.

Here are the log entries, the STARTTLS is failing

Sep 23 16:19:01 rtpsfimr001 sendmail[2591]: [ID 801593 mail.error]
j8NKAQS2029739: STARTTLS=client, error: connect fail

ed=-1, SSL_error=5, timedout=0, errno=131

Sep 23 16:19:01 rtpsfimr001 sendmail[2591]: [ID 702911 mail.notice] ruleset=tls_server, arg1=SOFTWARE, relay=mail.mass-

systems.co.uk, reject=403 4.7.0 TLS handshake failed.

Sep 23 16:19:02 rtpsfimr001 sendmail[2591]: [ID 801593 mail.info]
j8NKAQS2029739: to=<test.user@mass-systems.co.uk>, de

lay=00:08:36, xdelay=00:00:01, mailer=esmtp, pri=301971, relay=dsl-relay1.gxn.net. [195.147.9.38], dsn=2.0.0, stat=Sent

(OK id=1EIv1C-0003kA-00)

220 dsl-relay1.gxn.net ESMTP Exim 3.16 #1 Fri, 23 Sep 2005 22:23:42 +0100

>>> EHLO rtpsfimr001.glaxo.com

250-dsl-relay1.gxn.net Hello rtpsfimr001.glaxo.com [192.58.204.11]

250-SIZE 10000000

250-ETRN

250-PIPELINING

250 HELP

>>> MAIL From:<burt.a.marshall@gsk.com> SIZE=2237

250 <burt.a.marshall@gsk.com> is syntactically correct

>>> RCPT To:<test.user@mass-systems.co.uk>

>>> DATA

250 <test.user@mass-systems.co.uk> is syntactically correct

354 Enter message, ending with "." on a line by itself

>>> .

250 OK id=1EIv1C-0003kA-00

<test.user@mass-systems.co.uk>... Sent (OK id=1EIv1C-0003kA-00)

Closing connection to dsl-relay1.gxn.net.

>>> QUIT

221 dsl-relay1.gxn.net closing connection


Any help would be greatly appreciated

Thanks in advance.
 
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