Cant send email through SMTP (post Office s003 SP1)

[CJM]

I have recently installed Office 2003 SP1 - I'm not sure if this is the
problem; I've only just noticed the problem, so can't guarantee that SP1 is
the cause.

I have multiple accounts configure in Outlook at both home and work. Up
until recently, all the accounts on my work machine worked fine; they
included one exchange account and several pop3/smtp accounts.

My Exchange account still works fine. My yahoo accounts still appear to
work. But 3 other account with 3 different mail servers cant send outgoing
mail. The problem went unnoticed for a while because when I sent an email
from one of the problematic accounts, it didnt works, but the exchange
account picked it up and handled it.

E.g. I create a new mail, and specify which account to use to send it; it
gets sent, but the email appears in my outbox as if it has been sent from
the exchange acount (and the recipient also sees that it has come from the
exchange account).

If I do the same with a yahoo acount, it works as normal.

I tried creating a new Outlook profile for testing. I added one of the
problematic POP3 accounts. I tried sending a test email, as described above;
without the exchange account to fall back on, Outlook instantly returns an
error message:

"Undeliverable:

Your message did not reach some or all of the intended recipients.

Subject: test2
Sent: 01/09/2004 14:00

The following recipient(s) could not be reached:

'(e-mail address removed)' on 01/09/2004 14:00
None of your e-mail accounts could send to this recipient."

Everything continues to work at home. I havent installed SP1 there, nor do I
have the exchange account, but at least it shows that the email acounts in
question do work themselves.

As I said before, all these accounts have worked fine for years. The only
significant change recently was the upgrade to SP1. Unfortunately, because
Outlook falls back to using the exchange account, I havent noticed when the
problems started occuring. In fact, the thing that alerted me, was the fact
that I kept 'mistakenly' sending emails through the exchange account! But
when it kept happening, I figured that even I couldnt make the same mistake
that many times, and that something else must be wrong!

I'm puzzled why the Yahoo accounts keep working though!

Any ideas?

Thanks...

 

[Diane Poremsky [MVP]]

is your yahoo account through the internet provider? Can you send mail
through the yahoo SMTP? (change the SMTP to use the yahoo SMTP) Are you
authenticating with the SMTP? What are the connection settings (account
properties, more settings button)?

--
Diane Poremsky [MVP - Outlook]
Author, Teach Yourself Outlook 2003 in 24 Hours
Coauthor, OneNote 2003 for Windows (Visual QuickStart Guide)
Author, Google and Other Search Engines (Visual QuickStart Guide)



Join OneNote Tips mailing list: http://www.onenote-tips.net/

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[CJM]

is your yahoo account through the internet provider?

Not sure what you mean here...

Can you send mail through the yahoo SMTP? (change the SMTP to use the

yahoo SMTP)

I could do that I assume, but it's not really a solution. I want to know
what the problem is, not a workaround.

Are you authenticating with the SMTP?

Yes, both the yahoo and the other pop3 account authenicate in the same way
[use incoming username/pwd]

What are the connection settings (account properties, more settings

button)?

There are too many to detail here... besides, I suspect this is not the
problem.

Previously, these accounts worked. Now they dont. Nothing has changed in
terms of account configuration.

What may have changed is Outlook, or something outside outlook.

 

[Brian Tillman]

Yes, both the yahoo and the other pop3 account authenicate in the
same way [use incoming username/pwd]

But that's not what Diane asked. Authenticating to the POP server is
different from authenticating to the SMTP (outgoing) server.

 

[Diane Poremsky [MVP]]

is your yahoo account through the internet provider?

Not sure what you mean here...

Do you pay yahoo for it directly or do you get it through an SBC or other
internet access provider?

yahoo SMTP)

I could do that I assume, but it's not really a solution. I want to know
what the problem is, not a workaround.

We just need to know if it works to rule out possible causes.

button)?

There are too many to detail here... besides, I suspect this is not the
problem.

What do you suspect is the problem then? If you are trying to send them
through using a method that isn't the current connection method, it's going
to fail.

Previously, these accounts worked. Now they dont. Nothing has changed in
terms of account configuration.

What may have changed is Outlook, or something outside outlook.

We won't know for sure unless we are either in front of your computer or
have all of the information we need.

 

[CJM]

Yes, both the yahoo and the other pop3 account authenicate in the
same way [use incoming username/pwd]

But that's not what Diane asked. Authenticating to the POP server is
different from authenticating to the SMTP (outgoing) server.

That *is* what Diane was asking. You were reading too much into the phrase
'POP3'.

I have several accounts configured. One is an exchange account the other are
POP3/SMTP accounts; the 'POP3' I refer to means one of the non-exchange
accounts, which uses POP3 for incoming and SMTP for outgoing. That is, the
'POP3' means 'POP3/SMTP/Non-Exchange Account' and not 'POP3 server'. OK, I
know if I had been more explicit, this misunderstanding may not have
happened. Can we assume that I know the difference between a POP3 server and
a SMTP server.

All the yahoo accounts and all the other accounts have their outgoing
servers configured in the same way. As stated in my previous email, all use
the 'Use Incoming Username & Password' option.

Incidently, I tried an failed to run a test with Thunderbird - this is
possibly to do with my lack of knowledge with Thunderbird!

I also tried the same test with Outlook Express, which returned a 550 error:
SMTP authentication failure...

However, my spam filter uses both the POP3 and SMTP servers successfully...

One of the problems that I have noticed and confirmed, is that if an
outgoing email fails for one account, Outlook automatically tries to use a
different account - hence why it was falling back to using my Exchance
server. I'm sure this is designed to be a clever feature from MS but yet
again it's a foolhardy decision.

Chris

 

[CJM]

Do you pay yahoo for it directly or do you get it through an SBC or other
internet access provider?

It's just a free yahoo account, with the pop3 access option enabled...

We just need to know if it works to rule out possible causes.

Yes, this works.

What do you suspect is the problem then? If you are trying to send them
through using a method that isn't the current connection method, it's going
to fail.

My colleagues have been getting their hands dirty investigating. They think
that the non-working servers are not configured correctly, which rather lets
Outlook off the hook. I'm not an expert on ESTMP sadly, but what they
suspect seems to make sense - that the server configuration has changed
recently and is no longer correct.

However, when you consider than these very email accounts work fine in
Outlook on my home PC... it leaves me just as confused!

We won't know for sure unless we are either in front of your computer or
have all of the information we need.

True.

My colleagues are priming some questions to ask the IPP about the mail
server configuration. Until we find out if that is where the problem lies,
there is no point in continuing this thread.

I'll post back when I have either proved it is a mail server issue, or have
discounted that possibility instead.

Thanks

 

[Diane Poremsky [MVP]]

Incidently, I tried an failed to run a test with Thunderbird - this is

possibly to do with my lack of knowledge with Thunderbird!

I also tried the same test with Outlook Express, which returned a 550
error:
SMTP authentication failure...

My guess is the failure is related to the other failures, not thunderbird
config.

However, my spam filter uses both the POP3 and SMTP servers
successfully...

I'd be looking at this - which filter? is it locally instaleld? disable it
and see if it works.

One of the problems that I have noticed and confirmed, is that if an
outgoing email fails for one account, Outlook automatically tries to use a
different account - hence why it was falling back to using my Exchance
server. I'm sure this is designed to be a clever feature from MS but yet
again it's a foolhardy decision.

Some people are mad that ms changed things in 2003 to allow the secondary
accounts to send at all - it used to be that exchange sent all mail. I don't
have a problem with using secondary SMTP's, but the reasons my accounts fail
is different than yours, so they don;t need to roll to the next.

 

[Diane Poremsky [MVP]]

My colleagues have been getting their hands dirty investigating. They

think
that the non-working servers are not configured correctly, which rather
lets
Outlook off the hook. I'm not an expert on ESTMP sadly, but what they
suspect seems to make sense - that the server configuration has changed
recently and is no longer correct.

However, when you consider than these very email accounts work fine in
Outlook on my home PC... it leaves me just as confused!

it could be a change in the configuration and how you access the account,
especially if you are 'inside' the network now and outside it at home (or
inside at home and outside now). Also, the spam filter may have used an
autoupdate that messed things up.

 

[CJM]

My guess is the failure is related to the other failures, not thunderbird
config.

It could be, but never having used Thunderbird before I can't guarantee it
one way or the other, so I'll just ignore it for now.

I'd be looking at this - which filter? is it locally instaleld? disable it
and see if it works.

The filter is MailWasher. It only checks the the POP3 traffic, and only when
I say so, so it's not a contributing factor in this case.

 

[CJM]

The plot thickens...

Apparently the IPP have updated the mail server software overnight, and the
server now responds correctly to ESMTP commands and appears to be working
fine.

So this seems to put them emphasis back on my work situation; ie, Outlook,
Exchange and the network configuration.

To be honest, it seems unlikely the Outlook is the culprit. It may not
behave the way I would like it to, but it seems unlikely that it is
contributing to the SMTP problem.

My colleagues are going to try and monitor the SMTP traffic further to see
if we can further narrow down the problem. I'll post back if there are
further Outlook specific questions or issues, or indeed if we figure out
what is going on...


Thanks

 

[Brian Tillman]

My colleagues are going to try and monitor the SMTP traffic further
to see if we can further narrow down the problem. I'll post back if
there are further Outlook specific questions or issues, or indeed if
we figure out what is going on...

You might also consider turning on message logging
(Tools>Options>Other>Advanced Options). It should trace the communication
between your client and the server. The logs can be found either in
C:\Windows\Temp or %TEMP%

 

[CJM]

Right... well everything seems to be back to normal! I can only assume that
the issue is the way my work network communicated with the mis-configured
mail servers. Though it is unclear what was happening at the IPP's end - it
appears they were making changes to the server configuration as late as last
night.

The outstanding question I have is whether we can configure or control
Outlook's behaviour when it has problems with sending mail; is there a
setting or reg hack we can use to enable/disable the behaviour where Outlook
will use an alternative account where sending via the original account
fails?

Thanks

 

[Diane Poremsky [MVP]]

The outstanding question I have is whether we can configure or control

Outlook's behaviour when it has problems with sending mail; is there a
setting or reg hack we can use to enable/disable the behaviour where
Outlook
will use an alternative account where sending via the original account
fails?

None that I'm aware of.

--
Diane Poremsky [MVP - Outlook]
Author, Teach Yourself Outlook 2003 in 24 Hours
Coauthor, OneNote 2003 for Windows (Visual QuickStart Guide)
Author, Google and Other Search Engines (Visual QuickStart Guide)



Join OneNote Tips mailing list: http://www.onenote-tips.net/

Vote for your favorite Outlook and Exchange utilities in the
Slipstick Ratings Raffle at http://www.slipstick.com/contest/

 

[Matt Hickman]

I tried creating a new Outlook profile for testing. I added one of the
problematic POP3 accounts. I tried sending a test email, as described above;
without the exchange account to fall back on, Outlook instantly returns an
error message: ....
'(e-mail address removed)' on 01/09/2004 14:00
None of your e-mail accounts could send to this recipient."

When sending mail via an SMTP server from an IP address outside its
domain to an email address also outside its domain, you are using that
SMTP server as a SMTP Relay agent. Because SMTP relay agents are used
extensively by spammers, they are usually locked down.

For example, with Exchange 2003, the default property for authenticated
users is "submit permission" while "relay permission" is left unchecked.
To allow authenticated users to use Exchange as a relay agent, you need
to check that permission (SMTP virtual server => properties => access =>
authentication => users) -- Also check relay restrictions to ensure
authorized computers are allowed to relay. You are not confined to
using the authenicated users group for permissioning.

On the Outlook (client) side, in e-mail accounts => more settings =>
Outgoing Server, check requires suthentication. If the email account
isn't in the AD, use a valid AD account. If the e-mail account is
a valid account for the AD Exchange is using, just check "use same
settings"

Your situation may be a bit different so YMMV.

--
Matt Hickman www.craig-consulting.com
...he had let himself be bulldozed by the odds against
him. He promised himself never again to pay any attention
to the odds, but only the issues.
- Robert A. Heinlein (1907-1988)
_Between Planets_ (c. 1951)

 

[Jason Coleman]

Hello,

I think I am having a similar, or the same problem.
I have an Exchange server local, and I have a POP3/SMTP server.

I have configured mail accounts for both, and I've set the SMTP server to be
the default one. However no matter what I do I can't get outgoing SMTP mail
to be sent by logging into the SMTP server and sending it through that
server. I have verified this by sending an email from Outlook, specified
that I use the SMTP account. When I check the message I sent, the headers
all indicate that the mail was sent by my Exchange server directly to the
recipient instead of coming from the SMTP server like it should have.

I also configured a separate mail client for the same SMTP server and that
works fine as I expect(messages sent from that client are received as though
from the SMTP server as expected and not from my Exchange server).

I don't believe it is a configuration issue with my SMTP mail server. I
have checked it multiple times, I have done the test and it succeeds in the
sendmail test and the test email has a correct header(indicating it was sent
through the SMTP server). But when I try and send a mail from Outlook to an
SMTP address, it always goes through Exchange.

Is there anyway I can address this behavior so Outlook doesn't try to
deliver the message through Exchange? I'm still learning Exchange so this
maybe a config setting on Exchange I'm thinking? Is there a delivery path
that I can remove that might making Exchange think it can deliver Internet
outbound emails?

Thank you!
-JAson