The Sorry State of Email

Posted by Tom on Tuesday, March 13, 2007 to Random Thoughts, Small Business

We host a large percentage of our client’s websites, so every so often I spend a good deal of time setting up email on various applications such as Outlook and Outlook Express. About a year ago a number of clients started to report problems when sending emails. Outgoing emails bounced back with error messages such as “we do not relay.” After investigating the matter it turned out that most major ISPs now require their customers to send via their outgoing SMTP server, meaning they don’t “relay” to our outgoing server anymore in order to minimize the spread of viruses and spam. Everything that helps fight spam!

In order to comply with this change of rules you need authenticate yourself to your ISPs outgoing email server by entering a username and password in your email client. Most ISPs have walkthroughs in the help sections of their websites that outline how to accomplish this for all popular email applications.

So last week I set up a new Vista machine for a client and encountered the “we do not relay” message again. OK, I thought, let’s call the ISP and get the SMTP address as well as the username and password for the account. So I did just that, but Outlook 2007 continued to reject the username/password. I kept checking my settings over and over again to no avail. The strange thing was that I could login fine at the ISPs website with the username and password that was given to me by the customer support agent. After 45 minutes of this frustration I called the ISP again only to find out that this account had been “dormant” for too long (because there was never a need for my client to login to anything) and needed to be “reactivated.” And after that was done, Outlook happily accepted the username and password and even sent email!

Here is one thing that I to this day still don’t understand. Why is it that some machines won’t send without authentication and others send just fine? My client has a second PC in his office that forgoes the ISPs outgoing mail server completely, but sends just fine. Anyone?

Sounds almost like a happy end, right? Well, not so fast. Another issue cropped up only minutes later. Most emails addressed to recipients overseas bounced back with an indication that the IP address of the ISPs mail server was identified as a spammer by whatever means. Now this is even more frustrating since it can be a lengthy process to get off these lists and even worse, two weeks later the IP could very well be back on the black list. And while the ISPs involved play the finger pointing game, my client is left with crippled email service.

Has email gone mad? Chime in.

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