IIS6 SMTP Problem

[sialivi]

I'm new to all this so I'll include the changes to the default settings I've done (hope I haven't left anything out)

* OS: Windows Server 2003 Service Pack 2 running on a dedicated server

* Domain: Let's call it example.com, http/ftp is working fine

* Firewall: Windows Firewall for the time being, port 21, 25 and 110 has been opened. Have also tried with firewall disabled on both server and client.

* SMTP and POP3 services have been installed and activated, confirmed by running telnet from the server to itself

SMTP:

* Address: Set to the server IP and port 25

* Authentication: Integrated Windows Authentication

* Delivery / Advanced / Fully-qualified domain name: example.com

* Security: added "info" (info is a user created under POP3 below)

* Domains: example.com

POP3:

* Port: 110

* SPA activated (have tried deactivated as well)

* Domain: example.com

* Mailbox: info (automaticly create user, let's assume the password was set to "infopassword")

On the clientside I've configured outlook 2003 like this:

* E-mail address: info@example.com

* User Name: info (or info@example.com depending on if SPA is active or not)

* Password: infopassword

* SPA activated (have tried deactivated as well, depending on what I set on the server)

* POP3: example.com

* SMTP: example.com

* More Settings/ Outgoing server / Use same settings as my incoming mail server

Result from "Test Account Settings...":

* Send test e-mail message: The specified server was found, but there was no response from the server.

* Find outgoing mail server (SMTP): Outlook could not connect to the outgoing mail server.

Telnet:

* Port 110 (POP3) responds normally

* Port 25: "Could not open connection to host on port 25, Connect failed

* Port 25 from the server itself: responds normally

Log:

* The only Port 25 references in the log is from the above local test, 127.0.0.1

ISP:

* I've contacted the company that host this dedicated server and made sure they aren't blocking any ports

What am I missing? FTP, HTTP, POP3 seems to work just fine but I'm getting nowhere with SMTP. Any help would be greatly appreciated cause I'm running out of ideas. Thanks.

[+BudMan MVC]

What virus scanner are you running - quite a few of them block 25 outbound by default now. PM me the IP of this server, an I will tell you if it answer on 25

[bobbba]

I'm no expert on smtp servers but it seems to me that your dns names aren't right. shouldn't the smtp and pop3 server be server.example.com?

do you have an Active directory? if so is example.com your external internet domain and is your windows AD domain the same?

if you have a different AD domain, myinternaldomain.local for example I would expect your smtp server to be server.myinternaldomain.local

[+BudMan MVC]

Does not matter what he stated in the post about the name.. Clearly he can get to the server by IP or by FQDN from his client, if

  Quote

Telnet:

* Port 110 (POP3) responds normally

* Port 25: "Could not open connection to host on port 25, Connect failed

* Port 25 from the server itself: responds normally

From this I assume its his client side blocking outbound on 25 - lots of virus scanners do this by default now..

Only other thing to check - he mentions the server to itself responds.. is this to its public IP or 127.0.0.1 - maybe smtp is not listening on public IP?. But I would bet the issue is on his client side with his virus scanner blocking outbound to 25. Or -- it could be his ISP, lots of ISPs also block outbound to 25 off of their network. Trying to stop virus/trojans/worms/etc from sending email of themselves or spam, keeping people from running their own smtp servers, etc..

[bobbba]

  BudMan said:

Does not matter what he stated in the post about the name.. Clearly he can get to the server by IP or by FQDN from his client

Ok, I didn't spot that in the detail, I just read the "smtp server = example.com" and thought that isn't going to work...

[sialivi]

  Quote

do you have an Active directory?

No

  Quote

he mentions the server to itself responds.. is this to its public IP or 127.0.0.1

Public IP

  Quote

What virus scanner are you running

None at the moment, to eliminate usual suspects

  Quote

shouldn't the smtp and pop3 server be server.example.com

I earlier tried with an MX set to mail.example.com but it made no difference so I removed it to simplify

  Quote

lots of ISPs also block outbound to 25 off of their network.

I'm pretty sure they don't but I'm going to check just to be sure

  Quote

But I would bet the issue is on his client side with his virus scanner blocking outbound to 25

I've tried both with and without and it made no difference. When it is turned on it detects that telnet tries to access port 25 and asks for permission, so it's not the clientside firewall.

[+BudMan MVC]

Can you telnet to any mail server on 25?

examples..

Trying 66.28.242.207...

Connected to mail.neowin.net (66.28.242.207).

Escape character is '^]'.

220-mail.neowin.net ESMTP

220-MagicMail Daemon with Built-In Anti-Spam

220 See http://www.linuxmagic.com for info

telnet gmail-smtp-in.l.google.com 25

Trying 72.14.205.27...

Connected to gmail-smtp-in.l.google.com (72.14.205.27).

Escape character is '^]'.

220 mx.google.com ESMTP z21si7624232qbc

If not -- then something on your machine is blocking, or your router, or your ISP is.. If those work - then its something on server end.

[sialivi]

You're right, it's my ISP. Thanks alot :)