Can't send email when on the road

QUESTION:
I travel a fair amount on business and use motel/hotel wireless networks. However, when using Outlook 2003 (SP2), unless I'm sending an e-mail to a subscriber who uses the same ISP as I, I cannot get an outgoing e-mail to go through. I get an error message "550 relaying mail to ******** is not allowed."

My ISP says that the problem is with the network and the network administrator says that the problem is with the ISP. Of course, I can use WebMail OK but I really want to use Outlook. Any ideas?
- Neal D.

ANSWER:
Your problem is a common one. Here's what's happening: You're trying to use the SMTP server (outgoing mail server) of the ISP that you use at home to send your email, but you aren't connected to the ISP's network; you're connected to the hotel's network. When you try to send mail to an address outside your ISP's domain from the hotel network, that requires "relaying," which means the SMTP server has to pass off the mail to another SMTP server to send the mail. Once upon a time, most SMTP servers allowed relaying, but because spammers use it to disguise where their spam is coming from, most ISPs now configure their SMTP servers to not allow relaying. Unfortunately, that means people who are traveling get caught in the middle.

What we can tell you is that the problem is with your ISP, or more specifically with the way its SMTP server is configured to determine who is or isn't authorized to use the SMTP based on whether they're connected to its network. There are other ways an ISP can authenticate users, such as requiring a username and password to send mail just as you have to use those credentials to download your mail from their POP server. Sometimes you can contact your ISP and ask if you can use password authentication for SMTP instead of network connection authentication. You'll then need to configure Outlook for SMTP authentication and enter your credentials. Another solution is to change your Outlook account settings to use the SMTP server of the wireless network provider, if they have one. This is a little bit of a hassle because it requires changing these settings and changing them back when you travel, but will allow you to send mail - unless the ISP you're using also prohibits sending mail from an email domain that doesn't match the current network connection.

In that case, one solution that might work if you have a desktop computer at home with a broadband "always on" connection is to set up your home computer to accept VPN connections and connect to it from your laptop at the hotel, then use its connection to your ISP to send your mail. If the home computer runs XP, you can connect to it via Remote Desktop and send your mail from the Outlook running on the home computer.