Cannot send email to one specific email address????

I'm the IT professional of a certain office. one specific person in the office cannot send email to one specific person outside the office.

We'll call this person address A.
and the person they cannot send email to, address B.

Address A cannot send email to address B.
Address B CAN send email to address A.

both companies are using outlook to check email
both compaines have an exchange server set up, but do not revieve their pop3 email through the echange server.
both companies are using the same shared hosting company. both offices can send email to anyone else in either office.

I set up address A's email address on a test computer outside the office, and was able to send email to subject B.

I'm baffled. There are no rules, no junk email filtering, nothing.

I also tried to set up address A to recieve pop3 email through the exchange server, and the same issue happened. Address B can send to Address A, but Address A cannot send to Address B, even when replying.
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scampgbConnect With a Mentor Commented:
Do you mean a problem with your ISPs server?
Are you configured to send outbound mail via your ISPs smarthost?
Hi ZaKapitan,

What exactly happens when A sends an email to B?  Do they get an NDR message back saying that it couldn't be delivered?
If so, can you please post that here - it'll help us work out what's happening.

One other thing:
> I set up address A's email address on a test computer outside the
> office, and was able to send email to subject B.

Can you please describe how exactly you set up A's email address on this other PC?

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ZaKapitanAuthor Commented:
ok, I spent the last 5 hours researching this problem, trying to find any other trends.

first, to answer the question: Address A sends an email to address B, and it leaves outlook successfully, but address B never recieves it. it does not come back, there are no errors, etc... it just does not get there.

Now, I wondered if any other people in the office also are unable to send address B email, and it turns out there are 4 or 5 other email addresses that cannot send email to address B.

Address B can send email to anyone, which makes me believe this is a receive error, not a send error...

I found another email address in the same office as address A that CAN send messages to addrecc B, we'll call this email address "c".

So C can send email to B, and B can send to C.

Here's the kicker: If address A sends an email to C, and then THAT email is forwarded to address B, it doesnt go.

A->B, no
B->A, yes

C->B, yes
B->C, yes

A-> C -> B, no

A and C are in the same office, same domain, different email address
B is in another office, on a different domain.

I'm absolutely baffled.

all emails send normally, and do not return with any errors. A and C are on the same domain, and B is on a different domain, but both are using the same web hosting company.

all email addresses can send email to every other known email address.

Another point:
If I set up a completely unrelated email account in outlook on computer A, address B STILL cannot recieve the email.

If I set up address A on a completely unrelated copmuter, then address B CAN recieve Email...

could it have something to do with IP addresses?
ZaKapitanAuthor Commented:
all email is set up through outlook, standard pop3/smtp
I don't blame you for getting confused with all of this!

How is your network (A & C) connected to the outside world?  Is it through a firewall that's using NAT to a single external address, or does each PC have it's own external address?

If it's the latter, then it could be related to the IP addresses.  The IP address that's getting mapped could be on a spam blacklist.

More likely, there's something on PC "A" that's causing the receiver to quietly delete the email.
This could be spyware or a virus.

Download and run Spybot and AdAware on the machine to check for that:
Spybot -
Adaware -

Make sure that the AV software is up-to-date, and then to a thorough virus scan.

The next thing to eliminate is Outlook altogether.
On PC "A":
Go to a command prompt and type:
telnet (address of SMTP server) 25

This is a test

(the blank lines and "." above are important.

This will send the email via SMTP straight to the server, bypassing Outlook.

Contact the recipient and see if they got it.

It's also worth speaking to the receipient to see if they can think of any cause.  They might have some spam-filtering software that's identifying your emails as junk.
ZaKapitanAuthor Commented:
both networks are connected through a router on a static IP address. If I use a standard webmail console (not outlook) to log in to address A, I CAN send email to address B.

Your test works, it DOES send an email.

I have not been able to see the recipient's computer, but according to him, he has no spam or mail filtering, and no firewall. I will hopefully be going down to check HIS computer sometime this week.
From what you've said, it sounds like there's a problem with Outlook on computer "A".  The telnet test I suggested is basically doing what Outlook would be doing.
However, there's a load of header info missing and no subject - so it could still be a problem with recipient filtering.

I didn't realise that you had access to computer "B".  I suggest you check their Outlook (assumed Outlook!) rules and Junk Mail filter.
ZaKapitanAuthor Commented:
ok, I went down and checked out computer "B", and ther is nothing wron on his side. He is using outlook express, and all settings seem to be fine.

What I did is set upi Email address "B" on my test computer at work, and tried to recieve email from computer "A". Id dit not get there.

I'm suspecting that copmuter A has some very specific problem with sending out the email to address B. I cannot for the life of me figure it out.
Sorry, I'm running out of ideas here!

From what you've said so far, it does sound like something on Computer A
Have you tried a reinstall of Outlook on it?
Also, have you done the usual spyware/anti-virus checks? :-)
ZaKapitanAuthor Commented:
I think it's actually a problem with the mailserver....

We played around with some settings for no reason, and sent some test emails, and finally, Computer A recieved this message:

Your message did not reach some or all of the intended recipients.
Subject: RE: Deposit 9/24

Sent: 9/28/2004 8:05 AM

The following recipient(s) could not be reached:

<address B> on 9/28/2004 8:05 AM

The message reached the recipient's e-mail system, but delivery was refused. Attempt to resend the message. If it still fails, contact your system administrator.

<address a>

I'm going to contact the ISP.

ZaKapitanAuthor Commented:
yes,I think it's a problem with that specific email addres on the ISP's server. Address B likes to play with settings, and it could possibly have locked a few emails that are preventing any other emails from that address...

I dont know what a smarthost is.
The smarthost is the ISP's mail server that you can use to send emails through.
Basically, you can configure your Exchange server to send all outbound emails to your ISP's smarthost.
The ISP's server then deals with the job of delivering it for you.

ZaKapitanAuthor Commented:
hey, you're right! it IS the smarthost... it was their problem... Thanks!

Glad that we got there in the end!

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