Sending email from OE over ISP connection while VPN connection exists

My sister has a conventional ADSL connection with Freedom to Surf via a
Netgear router. Sometimes she needs to access her network at work so she has
VPN software (not sure which) to set up a VPN connection.

I was trying to configure Outlook Express so it would still send and receive
email via her broadband connection to F2S's POP and SMTP servers while the
VPN session was in place. When the VPN is active, ipconfig shows two LAN
connections and IP addresses: the real one to the router and the virtual one
provided by the VPN.

Reading POP mailboxes is fine: indeed while OE's mail accounts were initally
set on "Use any connection", it quite happily read the POP mail over the VPN
connection! But even with all the mail accounts explicitly set to "LAN
connection", I cannot send SMTP mail while the VPN is active: I get a
"cannot relay" error which normally means that I am trying to access an SMTP
server via a "foreign" ISP (ie one that doesn't own the SMTP server). But
OE's status window shows that all transactions, both reading POP and sending
SMTP are going over the LAN connection, so the presence of the VPN should be
irrelevant.

What's going on? I could probably solve the problem by configuring SMTP to
authenticate with the same user ID as for reading POP, so that if traffic
does go over the VPN connection instead of the LAN connection, it will not
be refused by F2S's SMTP server. But that's solving the wrong problem: if
there are two ways of connecting and OE is explicitly set to use one of
them, and its status window confirms that this is what is happening, then
why am I getting symptoms of data going over the other connection? And
anyway, the VPN connection will be slower than the direct LAN connection
because of all the encryption.

(I've just remembered that I need to set Internet Explorer explicitly to use
the LAN connection as well, otherwise that may sometimes access web pages
via the VPN connection!)

On 19 Oct 2006, "Martin Underwood" <a@b> wrote:

>Reading POP mailboxes is fine: indeed while OE's mail accounts were initally
>set on "Use any connection", it quite happily read the POP mail over the VPN
>connection! But even with all the mail accounts explicitly set to "LAN
>connection", I cannot send SMTP mail while the VPN is active: I get a
>"cannot relay" error which normally means that I am trying to access an SMTP
>server via a "foreign" ISP (ie one that doesn't own the SMTP server). But
>OE's status window shows that all transactions, both reading POP and sending
>SMTP are going over the LAN connection, so the presence of the VPN should be
>irrelevant.

What happens if you try to traceroute to the SMTP server ? Is it really
going via just the F2S connection or into the VPN and therefore it would
appear as a 'foreign connection' wrt F2S... I don't use VPN here at all
but get the impression that some aspects of Windows related network use
will depend on the *last* TCP/IP connection, so may take on the route
set up last, and in that case, could be going via the VPN (whatever
you were wanting to happen!).


>(I've just remembered that I need to set Internet Explorer explicitly to use
>the LAN connection as well, otherwise that may sometimes access web pages
>via the VPN connection!)

MS Outlook Express uses (AFAIK) the same connection control as MS IE (so if
you set MS IE to "work offline", MS OE will also think you are 'offline'
yet Firefox and Opera, and various [but not all, as some others depend
on Microsoft's settings too] other applications will still work.

Of course you could check whether external sites report the F2S IP, or one
from the work's network allocated when the VPN connection is established.
www.danasoft.com/sig/mywebpages.jpg (or http://ipcheck.dyndns.org AFAICR)
will show you the IP address if viewed with a browser (and try MSIE and
some *other* browser to see if it's the Microsoft setup giving the problem)

"Martin Underwood" <a@b> wrote in message
news:45377dd5$0$8749$(E-Mail Removed)...
> My sister has a conventional ADSL connection with Freedom to Surf via a
> Netgear router. Sometimes she needs to access her network at work so she
> has VPN software (not sure which) to set up a VPN connection.
>
> I was trying to configure Outlook Express so it would still send and
> receive email via her broadband connection to F2S's POP and SMTP servers
> while the VPN session was in place. When the VPN is active, ipconfig shows
> two LAN connections and IP addresses: the real one to the router and the
> virtual one provided by the VPN.
>
> Reading POP mailboxes is fine: indeed while OE's mail accounts were
> initally set on "Use any connection", it quite happily read the POP mail
> over the VPN connection! But even with all the mail accounts explicitly
> set to "LAN connection", I cannot send SMTP mail while the VPN is active:
> I get a "cannot relay" error which normally means that I am trying to
> access an SMTP server via a "foreign" ISP (ie one that doesn't own the
> SMTP server). But OE's status window shows that all transactions, both
> reading POP and sending SMTP are going over the LAN connection, so the
> presence of the VPN should be irrelevant.
>
> What's going on? I could probably solve the problem by configuring SMTP to
> authenticate with the same user ID as for reading POP, so that if traffic
> does go over the VPN connection instead of the LAN connection, it will not
> be refused by F2S's SMTP server. But that's solving the wrong problem: if
> there are two ways of connecting and OE is explicitly set to use one of
> them, and its status window confirms that this is what is happening, then
> why am I getting symptoms of data going over the other connection? And
> anyway, the VPN connection will be slower than the direct LAN connection
> because of all the encryption.
>
> (I've just remembered that I need to set Internet Explorer explicitly to
> use the LAN connection as well, otherwise that may sometimes access web
> pages via the VPN connection!)
>

I have had this issue before. Depending upon the type / setup of the VPN,
you will find that in some instances ALL traffic is routed over the VPN.
This is very annoying if you are "working from home" and want to undertake a
bit of browsing that you know your company would not approve...