Outlook 2003 Message-ID madness!

[Jason McClellan]

Reposting message previously from exchange.misc forum due to no replies!
-----------------------------------------------------------


Hi all... I have recently acquired Exchange 2003 along with enough CAL's
for all my users, which includes Outlook 2003. So, I have been upgrading
users to O2K3, most are now using the new version, but I haven't got
Exchange installed yet.

A number of my users have recently started complaining that some of our
contacts are not receiving their emails. Upon further investigation with
the admins at the receiving end, it seems that their spam filters are
dropping mails from some people due to a lack of the message-id header - the
Outlook 2003 users. I found mention online about Outlook 2003 deliberately
omitting the message-id, since it 'technically' still RFC compliant -
another Microsoft "feature".. but, very little information seems to be
available on this matter! I could find nothing official at all, only remarks
from other users, such as this one; and few of those even..

http://extelligence.ringlet.net/roam/archives/000018.html

Questions are - does anyone know some way to either have Outlook 2003 add
the message-id header, or some way to add it between outlook and the SMTP
server? Can anyone confirm this issue or point me towards some official
mention (ie. MS's website?)? Can anyone confirm that Exchange 2003 DOES add
the message-id header to outgoing messages from Outlook 2003 clients?

Thanks in advance for your help.
Jason

 

[neo [mvp outlook]]

Go to google's newsgroup search feature and search
microsoft.public.outlook.* for items posted by jeff stephenson [msft] for
items concerning this issue. it should answer your question as to why
microsoft dropped adding the message-id and why it shouldn't be a problem if
the smtp server is doing what it is supposed to be doing. (if you can't find
it, let me know since i know i paraphrased at least once or twice and should
be able to find the ones i posted.)

Exchange 2003 does attach a message id to all internet bound messages. If
the internal server that the site uses doesnt, might want to try bouncing a
few through Windows 2003 SMTP server (part of IIS) to see if you can get a
temporarily solution up in place before moving on to Exchange 2003. Outside
of that, many are having to go back to their 3rd party spam solution
providers and look for updates to deal with this change.

 

[Jason McClellan]

Thanks for the info. I did the search, read the messages I could find.
Nothing there I didn't already know, regarding why it's not there anymore.
I just thought that there would be at least some mention of this from MS..
like the KB or something.

I already own Exchange, it's just not implemented yet. I am looking for an
interim solution only. Currently we're using Software602's Lansuite, it's
served fairly well for 4 years, but does not add a message-id. Is it part
of some spec that servers must add this? What says that the smtp server is
'supposed' to do this? If it is just an implied 'good idea' that's one
thing.. but if it's part of a spec somewhere, I'll submit a bug
report/feature request on it.

Are you suggesting that the SMTP service alone will add the header? Only
2003 svr. SMTP, or will 2000 do it too? This would be exactly the kind of
temporary solution I'm looking for. I could simply enable the smtp service
(I assume I can select the network interface to bind it to somehow.. ?) on
the LAN only and use it to forward from my users to my existing SMTP server
for transmission. (changing ports on the existing server's LAN interface as
needed)

The problem isn't MY spam solution, it's OTHER people's spam solutions..
like archaic stuff that drops on hard rules rather than scoring.. this is
what started this, one of our business contacts had some rules, one of which
was if it had no message-id, the message was routed to the bit bucket.. not
even a notification to a soul. Irresponsible administration in my opinion..
but anyway..

Thanks for your help
Jason

Go to google's newsgroup search feature and search
microsoft.public.outlook.* for items posted by jeff stephenson [msft] for
items concerning this issue. it should answer your question as to why
microsoft dropped adding the message-id and why it shouldn't be a problem if
the smtp server is doing what it is supposed to be doing. (if you can't find
it, let me know since i know i paraphrased at least once or twice and should
be able to find the ones i posted.)

Exchange 2003 does attach a message id to all internet bound messages. If
the internal server that the site uses doesnt, might want to try bouncing a
few through Windows 2003 SMTP server (part of IIS) to see if you can get a
temporarily solution up in place before moving on to Exchange 2003. Outside
of that, many are having to go back to their 3rd party spam solution
providers and look for updates to deal with this change.

Reposting message previously from exchange.misc forum due to no replies!
-----------------------------------------------------------


Hi all... I have recently acquired Exchange 2003 along with enough CAL's
for all my users, which includes Outlook 2003. So, I have been upgrading
users to O2K3, most are now using the new version, but I haven't got
Exchange installed yet.

A number of my users have recently started complaining that some of our
contacts are not receiving their emails. Upon further investigation with
the admins at the receiving end, it seems that their spam filters are
dropping mails from some people due to a lack of the message-id header - the
Outlook 2003 users. I found mention online about Outlook 2003 deliberately
omitting the message-id, since it 'technically' still RFC compliant -
another Microsoft "feature".. but, very little information seems to be
available on this matter! I could find nothing official at all, only remarks
from other users, such as this one; and few of those even..

http://extelligence.ringlet.net/roam/archives/000018.html

Questions are - does anyone know some way to either have Outlook 2003 add
the message-id header, or some way to add it between outlook and the SMTP
server? Can anyone confirm this issue or point me towards some official
mention (ie. MS's website?)? Can anyone confirm that Exchange 2003 DOES add
the message-id header to outgoing messages from Outlook 2003 clients?

Thanks in advance for your help.
Jason

 

[Jason McClellan]

Ok, to follow up on your suggestion.. I installed the SMTP service in W2K
pro, which I assume would be the same as the SMTP service in W2K server.. I
sent a test message using O2K3 to myself through my isp, and as expected
there is no message-id within it. Then I set outlook to send to localhost
and sent a message that way. That one DOES have the message-id. So, it
appears that the W2K SMTP service does add the header! That's great!

So what I have in mind is this; I'll change my current SMTP server to
listen on port 25 on the Internet interface only. That will leave the SSL
SMTP server listening on the LAN on a different port. Then I can set the
SMTP service to listen on the LAN on port 25. If I set the SMTP service to
use my SSL SMTP as 'smarthost', the end result should be what I need.

Hmm.. Just tried this.. and in the 'smarthost' field of the SMTP Virtual
Server properties, it won't let me define a port!

Anyone know how I can define a smarthost with custom port number in the SMTP
server properties?

Thanks

Go to google's newsgroup search feature and search
microsoft.public.outlook.* for items posted by jeff stephenson [msft] for
items concerning this issue. it should answer your question as to why
microsoft dropped adding the message-id and why it shouldn't be a problem if
the smtp server is doing what it is supposed to be doing. (if you can't find
it, let me know since i know i paraphrased at least once or twice and should
be able to find the ones i posted.)

Exchange 2003 does attach a message id to all internet bound messages. If
the internal server that the site uses doesnt, might want to try bouncing a
few through Windows 2003 SMTP server (part of IIS) to see if you can get a
temporarily solution up in place before moving on to Exchange 2003. Outside
of that, many are having to go back to their 3rd party spam solution
providers and look for updates to deal with this change.

Reposting message previously from exchange.misc forum due to no replies!
-----------------------------------------------------------


Hi all... I have recently acquired Exchange 2003 along with enough CAL's
for all my users, which includes Outlook 2003. So, I have been upgrading
users to O2K3, most are now using the new version, but I haven't got
Exchange installed yet.

A number of my users have recently started complaining that some of our
contacts are not receiving their emails. Upon further investigation with
the admins at the receiving end, it seems that their spam filters are
dropping mails from some people due to a lack of the message-id header - the
Outlook 2003 users. I found mention online about Outlook 2003 deliberately
omitting the message-id, since it 'technically' still RFC compliant -
another Microsoft "feature".. but, very little information seems to be
available on this matter! I could find nothing official at all, only remarks
from other users, such as this one; and few of those even..

http://extelligence.ringlet.net/roam/archives/000018.html

Questions are - does anyone know some way to either have Outlook 2003 add
the message-id header, or some way to add it between outlook and the SMTP
server? Can anyone confirm this issue or point me towards some official
mention (ie. MS's website?)? Can anyone confirm that Exchange 2003 DOES add
the message-id header to outgoing messages from Outlook 2003 clients?

Thanks in advance for your help.
Jason

 

[neo [mvp outlook]]

Jeff is a Microsoft employee and I think this is about the best you are
going to get at this point since he was involved in Outlook 2003's
development.

RFCs that you would want to point support folks to is 2821/2822 for
server/server communication and 2476 for client/server.

Not sure if the SMTP service part of IIS5 will add the message-id since
Windows 2000 was released before the date shown on rfc 2821/2822. I was
just making a WAG that it might be a possible temporary solution to the
problem at hand since I know that the IIS/SMTP service of Windows
2000/XP/2003 can be bound to a specific IP or all unassigned. Guess it
shouldn't be to hard to take a Windows 2000 (SP4) and Windows 2003 server to
confirm what does and doesn't fit the bill.

At the very least, you get confirmation that Outlook 2003 doesn't add a
message-id to items sent via SMTP, there is no built-in option to get it
added, and that the issue has been raised before in this forum and does
cause issues with 3rd party spam suppression products. Not an answer you
wanted to hear most likely, but it is an honest one.

Thanks for the info. I did the search, read the messages I could find.
Nothing there I didn't already know, regarding why it's not there anymore.
I just thought that there would be at least some mention of this from MS..
like the KB or something.

I already own Exchange, it's just not implemented yet. I am looking for an
interim solution only. Currently we're using Software602's Lansuite, it's
served fairly well for 4 years, but does not add a message-id. Is it part
of some spec that servers must add this? What says that the smtp server is
'supposed' to do this? If it is just an implied 'good idea' that's one
thing.. but if it's part of a spec somewhere, I'll submit a bug
report/feature request on it.

Are you suggesting that the SMTP service alone will add the header? Only
2003 svr. SMTP, or will 2000 do it too? This would be exactly the kind of
temporary solution I'm looking for. I could simply enable the smtp service
(I assume I can select the network interface to bind it to somehow.. ?) on
the LAN only and use it to forward from my users to my existing SMTP server
for transmission. (changing ports on the existing server's LAN interface as
needed)

The problem isn't MY spam solution, it's OTHER people's spam solutions..
like archaic stuff that drops on hard rules rather than scoring.. this is
what started this, one of our business contacts had some rules, one of which
was if it had no message-id, the message was routed to the bit bucket.. not
even a notification to a soul. Irresponsible administration in my opinion..
but anyway..

Thanks for your help
Jason

Go to google's newsgroup search feature and search
microsoft.public.outlook.* for items posted by jeff stephenson [msft] for
items concerning this issue. it should answer your question as to why
microsoft dropped adding the message-id and why it shouldn't be a

problem

if
the smtp server is doing what it is supposed to be doing. (if you can't find
it, let me know since i know i paraphrased at least once or twice and should
be able to find the ones i posted.)

Exchange 2003 does attach a message id to all internet bound messages. If
the internal server that the site uses doesnt, might want to try

bouncing

a
few through Windows 2003 SMTP server (part of IIS) to see if you can get a
temporarily solution up in place before moving on to Exchange 2003. Outside
of that, many are having to go back to their 3rd party spam solution
providers and look for updates to deal with this change.

header -
the DOES
add

 

[Jason McClellan]

No, that's a fine answer. It pointed me in the right direction! Just seems
silly to remove something like that, even if it is technically optional..
how hard is a checkbox to enable/disable it? anyway, just ranting..

Since you posted that, I have been trying to make it work. I confirmed that
sending mail through myrealbox.com (my mail provider) with Outlook 2003
results in no message-id (already knew that!).

I setup the SMTP service on W2K. If I send the same message from outlook to
'localhost', it then relays it on, and in the process it DOES add the
message-id header. So, this could be a good temporary solution.

But, I would want the SMTP service to receive from my clients on port 25 as
usual, then forward the mail to my existing server which is on another port
on the LAN. It would continue to receive from the 'net on the WAN
interface. The 'smarthost' setting seems to work good for this and I can
set another port no problem. I just have to figure out how to make it send
on SSL.. this is because with my current server, I can set the port for SMTP
and SSL SMTP separately, and select which interface each is active on, but I
can't set different ports for one service on two interfaces.

Thanks for your help.

Jeff is a Microsoft employee and I think this is about the best you are
going to get at this point since he was involved in Outlook 2003's
development.

RFCs that you would want to point support folks to is 2821/2822 for
server/server communication and 2476 for client/server.

Not sure if the SMTP service part of IIS5 will add the message-id since
Windows 2000 was released before the date shown on rfc 2821/2822. I was
just making a WAG that it might be a possible temporary solution to the
problem at hand since I know that the IIS/SMTP service of Windows
2000/XP/2003 can be bound to a specific IP or all unassigned. Guess it
shouldn't be to hard to take a Windows 2000 (SP4) and Windows 2003 server to
confirm what does and doesn't fit the bill.

At the very least, you get confirmation that Outlook 2003 doesn't add a
message-id to items sent via SMTP, there is no built-in option to get it
added, and that the issue has been raised before in this forum and does
cause issues with 3rd party spam suppression products. Not an answer you
wanted to hear most likely, but it is an honest one.

Thanks for the info. I did the search, read the messages I could find.
Nothing there I didn't already know, regarding why it's not there anymore.
I just thought that there would be at least some mention of this from MS..
like the KB or something.

I already own Exchange, it's just not implemented yet. I am looking for an
interim solution only. Currently we're using Software602's Lansuite, it's
served fairly well for 4 years, but does not add a message-id. Is it part
of some spec that servers must add this? What says that the smtp server is
'supposed' to do this? If it is just an implied 'good idea' that's one
thing.. but if it's part of a spec somewhere, I'll submit a bug
report/feature request on it.

Are you suggesting that the SMTP service alone will add the header? Only
2003 svr. SMTP, or will 2000 do it too? This would be exactly the kind of
temporary solution I'm looking for. I could simply enable the smtp service
(I assume I can select the network interface to bind it to somehow.. ?) on
the LAN only and use it to forward from my users to my existing SMTP server
for transmission. (changing ports on the existing server's LAN interface as
needed)

The problem isn't MY spam solution, it's OTHER people's spam solutions..
like archaic stuff that drops on hard rules rather than scoring.. this i s
what started this, one of our business contacts had some rules, one of which
was if it had no message-id, the message was routed to the bit bucket.. not
even a notification to a soul. Irresponsible administration in my opinion..
but anyway..

Thanks for your help
Jason

Go to google's newsgroup search feature and search
microsoft.public.outlook.* for items posted by jeff stephenson [msft] for
items concerning this issue. it should answer your question as to why
microsoft dropped adding the message-id and why it shouldn't be a

problem

if
the smtp server is doing what it is supposed to be doing. (if you

can't
find

it, let me know since i know i paraphrased at least once or twice and should
be able to find the ones i posted.)

Exchange 2003 does attach a message id to all internet bound messages. If
the internal server that the site uses doesnt, might want to try

bouncing

a
few through Windows 2003 SMTP server (part of IIS) to see if you can

get

a 2003
add