A customer needed some help with microsoft outlook (receiving emails but not able to send). He has a new laptop & the wife has an older laptop.

Once I get there, it starts looking a lot more complicated. They are running microsoft small business server, with exchange server.

I think: this shouldn’t be too difficult, I was once an NT system administrator (10 years ago!), so I should be able to fix a small mis-configuration.

They are only using 1 email account (exchange server is probably overkill), so it’s looking promising.

Apparently the whole system was set up by a somewhat unreliable computer technician, who could not (or would not) fix all the issues with the system.

I look at the server & after some time familiarising myself with the setup, I notice that the email account is close to its max quota. Just to stop the hassle of email messages about “you are going to exceed your limit”, I increase the max limit.

Outlook on the older laptop is not receiving or sending emails… the wife connects to the server via remote desktop & runs outlook on the exchange server… that’s not right… but it works.

The new laptop is a little better… it seems to show the email contents (ie the received emails) correctly, but cannot send emails.

I cannot be sure if the exchange server is misconfigured, and tracking down a slight mis-config could take a long time…

I look at the outlook configuration on the 2 laptops & I see that outlook has 2 accounts:
– an exchange server account… that is normal
– an account that connects directly to the isp account… now this shouldn’t be necessary, the exchange server should handle that.

Anyway, I change the order of the accounts, so that the exchange server account is first, but it still doesn’t work.

It looks like my predecessor might have had some trouble configuring the exchange server, so he tried to work around it by setting up the direct isp connection (the way I’d expect outlook to work without the exchange server).

Now I try many combinations with outlook (over 2 visits) but I just cannot get outlook to work consistently & I don’t have the diagnostic knowledge of outlook & exchange server to be able to fix everything.

I can ping the isp mail server, but cannot get outlook nor outlook express to connect to the isp mail server… very odd.

There is not much info on the web, so that doesn’t help.

In the end, I admit defeat & recommend that the customer finds someone who specialises in exchange server, as there could be multiple problems; and although I’d love to fix the problem, it would take a lot of my time & it wouldn’t be fair to expect the customer to wait while I spend days experimenting, when all they want is to have it fixed “now”.

Maybe someone can point me towords a good resource for diagnosing exchange server / outlook problems?