Virgin Media Community

[engineer350]

Having problems setting up Microsoft Exchange 2019 to send emails through my Virgin Media Account, I had Exchange 2010 set up fin and all worked, but although I have set up the Exchange 2019 send connector to send through my Virgin Media account it is not working.

Can anyone help or advise?

[Anonymous]

you should be sending though your exchange email. VM email is not exchange based

[Ayisha_B]

Thanks @Anonymous 🙂

Let us know if you have any other questions @engineer350

[engineer350]

Thank you for your reply, smtp was working before from my SBS 2011 with Exchange 2010 once I changed the port in Exchange from Port 25 to Port 465, now that I have installed Exchange 2019 it will not send through VM, still trying to find my way around Exchange 2019 may be the port setting again

[ravenstar68]

Have you checked your error logs.

Also if you are using port 465 to relay - have you set it to use SSL/TLS?

Tim

[ravenstar68]

Just so people understand what the OP's situation is.

The OP is running their own Microsoft Exchange email server, I believe on their VM residential IP address.  (I've assisted with other issues in the past)

While running a mail server on a DHCP allocated address is NOT recommended, it's not expressly forbidden either.  In the OP's favour is the fact that although allocated via DHCP - VM public IP addresses rarely change.

However because they are Dynamic, they are listed on Spamhaus' PBL, so in order to send mail from such servers, The OP is sending via Virgin Media's outbound SMTP relays, or should I say trying to.

Unless Microsoft have changed the relay connectors since last I checked we may have a problem though.

smtp.virginmedia.com ONLY allows connections using Implicit SSL/TLS on port 465.

IIRC Microsoft Exchange ONLY supports Explicit SSL/TLS (via the StartTLS command)

To get round this the OP could use something like stunnel - and set the configuration so it listens on the localhost (127.0.0.1 or ::1) on an unencrypted port and then sets up a connection to smtp.virginmedia.com on port 465 SSL/TLS.

Tim

[engineer350]

Thank you for your reply, I am by no means and expert so I understand what you are saying a little, but I have managed to get around the problem anyway, have installed a program called hmailserver https://www.hmailserver.com I send emails from my Outlook to Exchange it then sends them to hmailserver, I have then configured this to send them to VM smtp, all works 

I am told I could just use hmailserver to send and receive my emails but I want to keep my calendar and other things supported by Exchange, because VM don't support Domains I pick my email up from my Domain managed by namesco.

Thank you for your help

[ravenstar68]

A bit involved as you've got 2 mail servers doing the job when you only need one.

stunnel is what it says on the tin, a secure tunnel.  I use it to telnet to smtp.virginmedia.com and imap.virginmedia.com when I want to double check that the servers up and running.  (Telnet only supports plain text connections - it doesn't handle SSL/TLS).  I simply Telnet localhost on the listening ports and stunnel makes the onward connection for me.

telnet localhost 25

220 know-smtprelay-8-imp cmsmtp ESMTP server ready
quit
221 Closing connection. Good bye.

Connection to host lost.

stunnel comes with a default configuration that listens on ports 110, 143 and 25 and connects to gmail using ports 995, 993 and 465 respectively..  It took all of 5 minutes to amend the file.

; **************************************************************************
; * Include all configuration file fragments from the specified folder     *
; **************************************************************************

;include = conf.d

; **************************************************************************
; * Service definitions (at least one service has to be defined)           *
; **************************************************************************

; ***************************************** Example TLS client mode services

[vm-pop3]
client = yes
accept = 127.0.0.1:110
accept = ::1:110
connect = pop3.virginmedia.com:995
verifyChain = yes
CAfile = ca-certs.pem
checkHost = pop3.virginmedia.com
OCSPaia = yes

[vm-imap]
client = yes
accept = 127.0.0.1:143
accept = ::1:143
connect = imap.virginmedia.com:993
verifyChain = yes
CAfile = ca-certs.pem
checkHost = imap.virginmedia.com
OCSPaia = yes

[vm-smtp]
client = yes
accept = 127.0.0.1:25
accept = ::1:25
connect = smtp.virginmedia.com:465
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.virginmedia.com
OCSPaia = yes

For your usage I would have done the following.

Remove the POP3 and IMAP listeners

Change the listening port for the SMTP connector

; **************************************************************************
; * Include all configuration file fragments from the specified folder     *
; **************************************************************************

;include = conf.d

; **************************************************************************
; * Service definitions (at least one service has to be defined)           *
; **************************************************************************

; ***************************************** Example TLS client mode services

[vm-smtp]
client = yes
accept = 127.0.0.1:2025
accept = ::1:2025
connect = smtp.virginmedia.com:465
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.virginmedia.com
OCSPaia = yes

Then fire up stunnel and finally set your Exchange connector to send to localhost port 2025

stunnel can be found here::

https://www.stunnel.org/downloads.html

Try setting it up on a different machine first if you're worried about messing up the mail server setup.

Tim

[engineer350]

Once again thank you for your help, I will give it a try sound interesting, I will let you know how I get on

[engineer350]

Thank you for your previous help, I did give stunnel a go but I cannot get it to work, I think I have followed your instructions Telnet is installed and working but I get the error log below

[ ] Initializing inetd mode configuration
[ ] Running on Windows 6.2
[ ] No limit detected for the number of clients
[.] stunnel 5.59 on x64-pc-mingw32-gnu platform
[.] Compiled/running with OpenSSL 1.1.1k 25 Mar 2021
[.] Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,OCSP,PSK,SNI
[ ] errno: (*_errno())
[ ] GUI message loop initialized
[ ] Initializing inetd mode configuration
[ ] Running on Windows 6.2
[.] Reading configuration from file stunnel.conf
[.] UTF-8 byte order mark detected
[!] stunnel.conf:1: "? Sample stunnel configuration file for Win64 by Michal Trojnara 2002-2020": No '=' found
[!] Configuration failed
[ ] Deallocating temporary section defaults

[!] Server is down