Bizarre - Outlook not using the right SMTP server

[Logan Noyes]

I've got Outlook 2003 SP2 configured with a single mail account on a
laptop. The mail account config has a specific outgoing (SMTP) server
configured. When the laptop user sends mail, it never uses that SMTP
server, instead the mail headers I see usually list one or two other
SMTP servers before getting to the recipient's ISP's SMTP server.

Anyone else with the same config sees headers that go straight from
their machines to the desired SMTP server and then to recipient's
ISP's SMTP server.

What's strange about this troublesome laptop is that the SMTP servers
its using change. When the user was in Boston, messages hopped
through an SMTP server that I think was run by the hotel's IT company
and then through a DSL address in Ohio. While the user was in Boston,
it always used the same pair. When the user traveled to North
Carolina and plugged into that hotel's set up, the headers started
showing hops through a different pair.

Bottom line: why isn't Outlook honoring the SMTP server I've
configured?

Thanks in advance!

 

[Gordon]

I've got Outlook 2003 SP2 configured with a single mail account on a
laptop. The mail account config has a specific outgoing (SMTP) server
configured. When the laptop user sends mail, it never uses that SMTP
server, instead the mail headers I see usually list one or two other
SMTP servers before getting to the recipient's ISP's SMTP server.

Anyone else with the same config sees headers that go straight from
their machines to the desired SMTP server and then to recipient's
ISP's SMTP server.

What's strange about this troublesome laptop is that the SMTP servers
its using change. When the user was in Boston, messages hopped
through an SMTP server that I think was run by the hotel's IT company
and then through a DSL address in Ohio. While the user was in Boston,
it always used the same pair. When the user traveled to North
Carolina and plugged into that hotel's set up, the headers started
showing hops through a different pair.

Bottom line: why isn't Outlook honoring the SMTP server I've
configured?

Thanks in advance!

If the user is not in a fixed location, then the smtp server will change
with whatever ISP the user happens to connect with....

 

[Logan Noyes]

If the user is not in a fixed location, then the smtp server will change
with whatever ISP the user happens to connect with....

Are you sure? I'm pretty sure DHCP only handles stuff like IP
address, gateway and DNS servers. Once connected to the Internet, I
would assume Outlook would simply talk directly to the SMTP server
that's configured in Outlook. In this case, his outgoing emails are
completely bypassing our designated SMTP server.

 

[Gareth]

Are you sure? I'm pretty sure DHCP only handles stuff like IP
address, gateway and DNS servers. Once connected to the Internet, I
would assume Outlook would simply talk directly to the SMTP server
that's configured in Outlook. In this case, his outgoing emails are
completely bypassing our designated SMTP server.

Yes, I posted about this phenomenon a number of years ago in relation to
Outlook Express - I've also seen a few (but only a few) other posts
describing the same thing in relation to Outlook and Outlook Express.

In any case I can't replicate the feature using my current setup (using
either Outlook or OE) but yes it certainly happens and there doesn't seem to
be an adequate explanation for it.

It's a bloody useful feature however and it's just a shame that it isn't
possible to set it up as standard. It seems to be a quirk with Outlook and
OE.

Gareth.

 

[Logan Noyes]

Yes, I posted about this phenomenon a number of years ago in relation to
Outlook Express - I've also seen a few (but only a few) other posts
describing the same thing in relation to Outlook and Outlook Express.

In any case I can't replicate the feature using my current setup (using
either Outlook or OE) but yes it certainly happens and there doesn't seem to
be an adequate explanation for it.

It's a bloody useful feature however and it's just a shame that it isn't
possible to set it up as standard. It seems to be a quirk with Outlook and
OE.

Gareth.

Thanks for the info, but its not a terribly useful feature. For
example, one of the servers that Outlook decided to use the other
night was one that had been blacklisted for spam, so many of my user's
recipients dropped or bounced his mails.

Do you have any idea if this was being driven by Outlook/OE or at the
OS level? I'd be very curious to know which subsystem is deciding to
bypass the specified setting and how it is deciding what to use.

 

[df]

I've got Outlook 2003 SP2 configured with a single mail account on a
laptop. The mail account config has a specific outgoing (SMTP) server
configured. When the laptop user sends mail, it never uses that SMTP
server, instead the mail headers I see usually list one or two other
SMTP servers before getting to the recipient's ISP's SMTP server.

Anyone else with the same config sees headers that go straight from
their machines to the desired SMTP server and then to recipient's
ISP's SMTP server.

What's strange about this troublesome laptop is that the SMTP servers
its using change. When the user was in Boston, messages hopped
through an SMTP server that I think was run by the hotel's IT company
and then through a DSL address in Ohio. While the user was in Boston,
it always used the same pair. When the user traveled to North
Carolina and plugged into that hotel's set up, the headers started
showing hops through a different pair.

Bottom line: why isn't Outlook honoring the SMTP server I've
configured?

Thanks in advance!

The common thing here is the hotel. As you may know, travelers face some
issues when trying to send email on a hotels guest network. Due to the fact
that the SMTP server that is configured in outlook will only accept email
from clients inside the ISP's network (Unless it's configured to use SMTP
AUTH). This poses a problem for travelers and hotel staff alike, travelers
can't send email and hotel staff have to become makeshift IT pros.

Alot of hotels these days employ devices that perform the billing,
accounting and a range of other functions. One of the functions of these
devices is to listen for outgoing SMTP requests, and redirect them to
another SMTP server that will accept the email.

It's totally transperant to the end user, unless they look at the email
headers then they see the different SMTP servers in the headers. But totally
hassle free for the corporate joe.

These devices will even ignore SMTP auth and redirect anyway.


P.S Some, not all devices will even MAC translate to computers with static
IP addresses, and proxy settings. So it "Just works" for the traveler.

 

[Logan Noyes]

The common thing here is the hotel. As you may know, travelers face some
issues when trying to send email on a hotels guest network. Due to the fact
that the SMTP server that is configured in outlook will only accept email
from clients inside the ISP's network (Unless it's configured to use SMTP
AUTH). This poses a problem for travelers and hotel staff alike, travelers
can't send email and hotel staff have to become makeshift IT pros.

Alot of hotels these days employ devices that perform the billing,
accounting and a range of other functions. One of the functions of these
devices is to listen for outgoing SMTP requests, and redirect them to
another SMTP server that will accept the email.

It's totally transperant to the end user, unless they look at the email
headers then they see the different SMTP servers in the headers. But totally
hassle free for the corporate joe.

These devices will even ignore SMTP auth and redirect anyway.


P.S Some, not all devices will even MAC translate to computers with static
IP addresses, and proxy settings. So it "Just works" for the traveler.

That's absolutely fascinating. Where do I find out more about these
devices? And If I absolutely positively want to make sure my SMTP
server is being used (which *does* accept authenticated connections
from anywhere in the Internet), is there a way around it? For
example, if I use SMTP on something other than port 25 will these
devices still "steal" the SMTP transactions?

Thanks for the info!

 

[df]

That's absolutely fascinating. Where do I find out more about these
devices? And If I absolutely positively want to make sure my SMTP
server is being used (which *does* accept authenticated connections
from anywhere in the Internet), is there a way around it? For
example, if I use SMTP on something other than port 25 will these
devices still "steal" the SMTP transactions?

Thanks for the info!

These guys are generally the market leader.

http://www.nomadix.com/

Info about them is thin on the ground i'm afraid.

This is some text from their user manual:

When SMTP redirection is enabled (for misconfigured or properly configured
subscribers), the

AG 3000 redirects the subscriber's E-mail through a dedicated SMTP server,
including SMTP

servers which support login authentication. To the subscriber, sending and
receiving E-mail is

as easy as it's always been. This function is transparent to subscribers


Much of what i've already told you i'm afraid.

I did however just do a test then. I set up a basic SMTP server on port 5000
at another location and connected via RDP to a computer we have inside one
of our hotel networks, and ran a telnet connection to the SMTP server on
port 5000 and it wasn't redirected, and was able to send email from telnet.
It seems that only connections on port 25 are redirected to another SMTP
server.

So your plan to set up an SMTP server on another port will work according to
my tests on the Nomadix deployed at one of our sites. I cannot say with
certainty that all devices behave the same way, but i'm 90% sure that they
would.


Good Luck.

 

[Logan Noyes]

These guys are generally the market leader.

http://www.nomadix.com/

Info about them is thin on the ground i'm afraid.

This is some text from their user manual:

When SMTP redirection is enabled (for misconfigured or properly configured
subscribers), the

AG 3000 redirects the subscriber's E-mail through a dedicated SMTP server,
including SMTP

servers which support login authentication. To the subscriber, sending and
receiving E-mail is

as easy as it's always been. This function is transparent to subscribers


Much of what i've already told you i'm afraid.

I did however just do a test then. I set up a basic SMTP server on port 5000
at another location and connected via RDP to a computer we have inside one
of our hotel networks, and ran a telnet connection to the SMTP server on
port 5000 and it wasn't redirected, and was able to send email from telnet.
It seems that only connections on port 25 are redirected to another SMTP
server.

So your plan to set up an SMTP server on another port will work according to
my tests on the Nomadix deployed at one of our sites. I cannot say with
certainty that all devices behave the same way, but i'm 90% sure that they
would.


Good Luck.

df - thanks for the info! You are awesome!

I'll report back with whether or not this works....hopefully my user's
in a hotel another day this week.