Can't send external mail

[Bizzaro31]

Ok, this is my problem. We just set up our office with Microsoft Small business server which came with exchange server on it. We already have email set up with our ISP that handles our "domain.com" email. We do not want to use exchange server for email. However, when setting up outlook to send mail out using our ISP's SMTP server, it doesnt work. But when using a different email client(thunderbird) it works just fine.

Seem's like outlook has some feature on it that only lets mail go out through the exchange server or something. Is there a policy or something that is causing this. I been pullin my hair out messing with connectors and everthing....nothing is working.....

We would like to use outlook with the Exchange server to use the contact and calender sharing features. Is it possible or will I have to use thunderbird?

Thanks
Matt

 

[Bizzaro31]

I forgot to mention.....I get "the connection to mail server was interrupted" as teh error when it does not send. I thought it might be the firewall or antivirus software causing that but the Thunderbird client works just fine so I ruled that out.

 

[Bizzaro31]

ok, here are some other trouble shooting steps taken so far.

1) can send using Thunderbird client.

2) can send when directly connect to the internet and not going through the server (server is doing routing to the internet but bypassed it and went directly to the broadband router)

3)cant send when on the internal network using outlook using both exchange account or ISP except when replying to the email message that was sent using Thunderbird and reply back too. In other words. The mail was sent using thunderbird to external user. He then relpied to it and it was downloaded to outlook. then it was replied to and it sent it out without a problem.

 

[Bizzaro31]

Ok, well, I seem to be talking to myself but whats new? Anyway....this is the latest. If I reboot the server, I can send email using either the external mail or exchange. But after about 5 to 10 minutes....it stops working again.....any Ideas?

I am going insane.

 

[Bizzaro31]

anyone have any Ideas?.....I can send from outlook express also.....just not outlook.

 

[Xanaxo]

Honestly it sounds like a client configuration problem. I wanted to say it could be a firewall not letting port 25 traffic go outbound from your clients but Thunderbird seems to work fine which should use this same port. Do you have ISA 2004 installed on the SBS server?

How do you have the Outlook profile configured? How many clients/computers/accounts have you tested this from?

Did you know SBS has a POP3 connector that you can configure to download mail from your ISP into your Exchange mailboxes? This would allow you to use Exchange MAPI connectivity and your get all the ooh's and aww's you are wanting.

Here is everything you need to know about this:

http://support.microsoft.com/?id=885685

Steven Parent [MSFT]

 

[Bizzaro31]

Well, its not the firewall since thunderbird and outlook express work fine. ISA 2004 is not installed.

As far as the outlook profile, Im not sure. I would say the default? All clients(5) have this problem.

I have the pop3 connector working. The clients have no problem getting the email using either the pop3 connector or directly connecting to the ISP. They just cant send using SMTP connector or SMTP to the ISP directly. I feel everything is setup right and after rebooting the server, everything works. Just stops working after about 5 to 10 minutes. I have everyone using outlook express right now for email.

I guess my next step is to look into the outlook profile.

Thanks for the response.

There is one other thing that also dosn't make sense that might be related. None of the clients can run windows update(acts like it does then it fails) and Microsoft Office would not activate....it would just quit when attempting. Both worked when hooked directly to the internet(broadband router) without using the server for routing. Same holds true for the outlook emails. If I connect it directly to the broadband router it sends out fine.

 

[Xanaxo]

Okay was unaware that it works when you reboot for a few minutes. I did a lot of reading and might have missed you saying that. Anyway, your issues with your clients seem like a proxy error or perhaps the default gateway isnt set right on your network interfaces. It's hard to say, but something certainly doesnt seem to add up.

What kind of connection do you have to the internet? Have you considered using SBS to host your own domain and make your Exchange server live? (maybe you are and I missed that point also)If you utilize the potential of SBS, your clients should never have to make a connection to the internet to send email, or recieve it. I am also curious what firewall you are working with.

Have a good day.

Steven Parent [MSFT]

 

[Bizzaro31]

The internet connection is DSL (SBC Yahoo). The server is being used with routing and remote access with its built in firewall. It then connects to a Linksys Broadband router with firewall. Each client also has windows firewall on it (disabled and tested still didnt work).

I would like to use the SBS to host the domain but the owner is too cheap. The ISP does not allow internal Email servers and will block them unless you pay for the static IP package and upgraded bandwidth. Since we get free email and web space with our domain register, he thinks it is a waste of money. Plus, this is what we have been using for the past few years and has been working just fine for such a small office. The server was installed last month.

I agree that it doesnt seem to add up, this is why I am going crazy. The Internet works just fine from all workstations and all applications. Nortons AV activation and live updates work. Just Microsoft products are having the problem. I was thinking it was some kind of policy setting the server has for Microsoft products that prevents it. Thought since the workstations were already running when the server reboots the policy might take a few minutes to kick in so the emails send during that time. I dont know....I am probally way off.

I will keep trying different things.

Thanks again for your responses

 

[Xanaxo]

I doubt it is a policy, but I cannot rule it out at this point. (I do not knowe policies as well as I should) The quickest way to check to see is to either look over your policies manually and see if they contain an element that would cause this, or you can disable them long enough to test. I would not recommend disabling the DC policy any longer than nessecary to test however. If you have a domain policy in place or any other policy I would recommend you disable them to test it first. I can say for sure that if this is a new server, by default, neither Windows 2003 or Exchange 2003 would have a policy of this nature.

I know PSS has a tool that will reset your polcies to default, but I do not have it available or know exactly what it is off the top of my head.

Hope this helps.

Steven Parent [MSFT]

 

[Bizzaro31]

one more thing. When I set the default mail server to the ISP, it is automaticly set back to Exchange server after a reboot or over a short period of time. How do I stop that.....I think if I find where that setting is I can find the other probelm.

 

[Xanaxo]

Did you test by disabling the policies?

Steven Parent [MSFT]

 

[Bizzaro31]

no, I looked into policies, but there was no policy that I could see installed. I heard form another forum to have SBC remove the port 25 block (he said by law they have to) from our account because it solved their problem. I put a request in. If that doesnt fix the send through the sbc account problem then it will fix using the built in SBS SMTP to send email......so either way it looks like a solution. I hope that fixes the SBC account send because if it doesnt then I will always wonder what happened. I set up so many servers and never had a problem like this. But I usually set it up from scratch...this one came pre-installed (was thinking of wiping it out and starting over). I had less problems setting up linux servers....lol

I still have no Idea why windows update and microsoft activation does not work either. I diabled all firewalls and still nothing. Maybe it is a messed up server install.