Table of Contents

• What are the major misconceptions about e-mail (outgoing)?


• What are the major misconceptions about e-mail (incoming)?


• What criteria should I use in choosing an e-mail server (and the people to manage it)?


• Sure, sure, we care about Internet standards. Don't we?


• What guidelines should the company use for setting e-mail policies?

Within an organization, you can make e-mail highly available, reliable and auditable-if you are willing to invest enough human and technical resources toward that goal. However, no amount of effort and expense can make external e-mail function like your corporate mail. Part of that is intentional. Some features of corporate mail systems (such as out of office notices, read receipts, address lookup and verification) carry security concerns. Getting Internet e-mail to work nearly like corporate e-mail can only be done on a piecemeal basis by making special arrangements with outside partners in the specific cases where you need corporate-level e-mail functionality.

All attempts to add reliability to SMTP after the fact (such as adding return receipt) have either failed or been withdrawn from use after massive abuse, primarily by spammers.

Just remember: E-mail isn't guaranteed. This issue causes your e-mail administrators no end of angst. One wrote, "Boy, do I struggle getting that one through to my marketing guy, who not only expects all e-mails to definitely get to the recipient but also expects me to be able to track whether they got it, how long they read it for, etc. When I first informed him-rather forcefully-that there is no guarantee of delivery, and hence he should not have any contractual or legal obligations dependent on e-mail delivery, he thought I was just being needlessly obstructionist, possibly incompetent."

A few more short points:

• Read mail server messages before you complain. Many end users act as though e-mail were magically delivered from their computer to the recipient's computer. In reality, each message transits a number of servers along the way. If faced with a temporary failure to deliver your message to the next-in-line server, e-mail servers retry the connection. (They are supposed to retry in a short period of time, such as 15 or 30 minutes, but a surprising number of servers wait for as long as 12 hours.) If the retry is unsuccessful after a while (say, four hours), the mail server may send the e-mail author a status update. Eventually, the server gives up and sends a bounce message. Your users should be taught to tell the difference between the words "permanent" and "temporary" before they freak out in the direction of the e-mail administrator.



• If the message doesn't reach the intended recipient, it isn't always the fault of the technology. Sending e-mail is like dialing a phone number: if the address isn't right, your mail won't go where you want it to.



• E-mail is never really private. If you want the message contents truly to be secret, encrypt the file first, and then send it as an attachment. A mail admin may rummage through the mail queue while trying to find the cause of a server problem. If it's in plain text, it can't be secret.

What are the major misconceptions about e-mail (incoming)?

End users make many false assumptions about the messages that land in their inboxes.

Often, users are confused about why they received a message when their names aren't in the To: header. There are many possible answers, benign and otherwise. For example, someone could have placed the user on a Bcc list. In reality, the addresses in the To: and Cc: headers do not necessarily bear any relation to the actual list of recipient addresses. It is only by convention that mail clients place the actual recipient addresses in those headers.

It's the less harmless messages that cause the problems.

From the server's point of view, the only thing that matters for routing is the e-mail envelope. This is easily visualized. Grab a sheet of paper, write any name on it (say, "Esther") and fold the page into an "envelope." Write a different name on the envelope (for example, "Sandy"). The envelope will be "routed" through the post office to Sandy, independent of whatever the envelope contains.