Getting the (E)Mail Through

At its best, email is fast, fun and tremendously productive. But email, like the weather, is largely unpredictable. That’s because it depends on the Internet, which belongs at once to everyone and no one. In short, no one’s in charge of making sure email gets through.

While there are no delivery guarantees, it is possible to tilt the odds in your favor. Here are some tips in order of importance.

Address Book. Most undelivered email fails because of a bad email address. Although email addresses are not case sensitive, everything else about an email address must be just right. You can avoid typos and misspellings by addressing email from verified addresses in your address book. This also prevents common substitutions, e.g. name@com for name@org or name@edu, and incorrectly transcribed addresses, i.e., my friend Michael spells his name Micheal; was that Coles, or Kohls, or Coals? Remember, even the owners of email addresses misspell them. Don’t click on Reply to send an email. Use your address book!

Sidestep SPAM Filters. Today, most hosts filter inbound email to quarantine or delete SPAM and viruses. Some hosts, notably AOL and Hotmail, are notoriously aggressive, generating a high percentage of false positives. Even Big Blue (the famous chess-playing IBM computer) can’t outwit SPAM filters. The best solution is an end-run around the filter: ask your contacts to add your email address to the list of accounts whose email will be accepted without filtering. This may be called a Friend’s List, Contact List, White List, Acceptance List, etc.

You Get What They Paid For. Some email accounts are more equal than others. Many users have so-called free (meaning ad-supported) email accounts. Others pay. You can’t sex them by looking at the email domain. For example, I have an email account at which is free, and an account at, which I pay for. It won’t surprise you to learn that email to my paid Yahoo! account gets through virtually all the time, with intelligent SPAM filtering, virus and spyware protection. Email to my Hotmail account is pokey, unreliable, and likely to wind up in the SPAM bin. The best defense against a pokey recipient is to join the fray. If you’re having difficulty getting through to a recipient who uses AOL, open an AOL account and send from there. Intra-ISP transmission is fast, and subject to few rejections and misclassifications.

Don’t Play in Traffic. Just as there are good and bad times to go to the mall, cross a busy street, or call a help desk for service, timing counts when sending email. As you might expect, first thing in the morning is a busy time for email, and Monday mornings are generally worst of all. Your email is more likely to get through quickly and with the least likelihood of loss if you send it later in the day, and in the middle of the week. Need more timing info? Check out the Internet Traffic Report .

Size Counts. Size counts in two ways. Large emails automatically receive a low priority and are delivered more slowly than small ones. And some emails, usually with large attachments, may be accepted on your end but turned away or just deleted on the receiving end. In general, emails less than 10 MB in size will get through — eventually.

Makeup Matters. The makeup of your email — how it looks and what it contains — matters. Not only do the Intenet routers assign a lower priority to email with attachments, but many receiving ISPs, including AOL, Gmail, Hotmail, Earthlink, and Yahoo!, check incoming mail for viruses and spyware, and machine-read email to filter for SPAM, and to place contextual ads.

HTML-formatted email and email with attachments that can harbor viruses or run spyware — including *.doc, *.html, *.exe, *.pif, *.swf, *.com, *.bat — will be processed more slowly, and sometimes mistakenly rejected or deleted. NB: AOL is infamous for deleting inbound email without notifying the sender or the recipient. Emails that include URLs, viz. website or email addresses, may also be misclassified. If your email address is not in your recipient’s Accept List, makeup with care! Your best bet is short, plain-text email with no attachments.

Consider The Alternatives. Email is free. You can’t pay anyone to guarantee when or if it’s delivered. Important communications need to be sent by postal mail or a parcel delivery service. For quick and easy communication with a friend or collaboration with a business partner, consider Instant Messaging (AOL, Yahoo!, MSN, Google, ICQ all offer free, and generally reliable services) or text messaging (Short Messaging Service). When it comes to communications, we can all take a lesson from the under-30 crowd.

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