Web Informant #132, 2 December 1998:
Delete this email now


The ongoing trials of Microsoft have brought a new dimension of paranoia to business computing. While it certainly has been entertaining to read the private emails of Gates & Co., the notion that anyone's business correspondence can be aired in public is certainly a fearful thought. I dare say none of us welcome the notion, and many of you might have spent the Thanksgiving holiday going back over your old emails and doing some house cleaning. Several well-meaning people have suggested that you should have corporate policies to delete your email as soon as possible. The idea being that once deleted, the record is swept clean and no more worries about what your correspondence.

I'll come clean and tell you that I use both Eudora and Outlook Express and keep copies automatically of all my outgoing emails. I've done so for years, and it is extremely helpful. Sometimes I forget what I said to a client, or a potential client, or someone who I interviewed for a story, or whatnot. Being able to sort through my outgoing mailbox and find the message has saved me tons of time and eliminated some embarrassing moments.

(promotion: If you want to know how to do this, get a copy of my Internet Messaging book. We talk about how to configure various email programs to automatically save copies and how to find them once you have saved them.)

Deleting your past emails sounds good in theory, but when you really begin to think about the concept, you find out that doing so is actually something quite hard to do. The trouble is that email lives in more than one place in your computing universe, and depending on what kind of system you are running and how diligent your network administrator is, you might not find all the places.

There are four issues to the deletion problem. First is the operation of your own computer operating system: deleting a file, whether that file is an email or a document, may just temporarily hide the file from view. Second is the backup issue: your network administrator may make tape backup copies of your email servers on a regular basis. Third is how the email software itself operates: some keep copies locally on your hard disk (like what I do with Eudora), some keep copies on the server itself (if you are running an IMAP system that is one way these operate), and some keep copies in both places. Finally is the problem of your correspondents, who may keep copies of your emails on THEIR machines, totally out of your control.

The first issue is the easiest to solve. If you are running Windows 95/98/NT, you can go right now to your trash can (oops, I mean Recycle Bin) and click on it and see what files you thought were deleted are still lurking about. If you are running 98, you can go to Programs|Accessories|System Tools|Disk Cleanup and it will take care of this for you. If not, (and if you are using a Mac) you can delete the files with the Delete key. You probably also want to look around your hard disk and see if there are temporary files that your email and word processing software (along with any other applications you use) has tucked away someplace: these ought to go as well.

The second issue is harder. Remember Ollie North? He thought he was deleting his PROFS messages forever, only to be faced with the very same messages down the road when he had to testify in front of Congress. That was because his email system was mainframe-based, and the mainframe people make backups on a regular basis. Once the right Congressional staffer got ahold of the right backup tape, Ollie was toast. If you are running Lotus Notes, Novell Groupwise, and Microsoft Exchange/Outlook, chances are good your network people also have backup tapes of your emails. So deleting them from your own local disk doesn't do much to keep the lawyers from getting copies later, if the lawyers know whom to ask.

Now, I think these backups play a valuable role. Back when I toiled in the trenches of Transamerica IS department, we needed backups because users did occasionally delete things they needed later. It was good to have the tapes to restore the files. What I do suggest is that you keep a limited supply of tapes (say one or two months' worth) on hand, or perhaps segregate individual user data from other kinds of corporate data. Still, you should be aware of your corporation's backup policy in any event.

But we still have to deal with the third issue, that of how your email software operates. Notes et al. can be configured not to save copies, but most corporations don't configure these products in this fashion. It makes it harder to use these products when people travel and want to replicate their mailboxes on their laptops. You should ask your email administrator what the situation is, and perhaps make some formal corporate policy here if this is a concern.

Here is where having a 100% pure Internet email system comes in handy. One of the nice features of these kinds of products is that they can be set to automatically delete email from the server when you collect your messages. You can also set the product to keep copies on the server, but most people only use this setting temporarily, otherwise their messages would pile up!

You also have a problem with how these email products delete messages too. Email products can work just like the overall operating system - lurking around your disk can be a special directory containing deleted messages. Eudora keeps these in its Trash folder, which you need to empty periodically by choosing the appropriate command. Again, read my book if you are interested in how to set up your software.

The final scenario (that of having packrat correspondents) is the hardest challenge. You can't be sure that everyone will practice the same kind of computing hygiene that you desire. One suggestion is to use encrypted email products to ensure that only your correspondents can view your messages. That is a good suggestion, although setting up these encryption tools isn't for the casual user.

There is also the issue that any Internet-based email travels around the Internet as plain text, which argues for encrypting these messages while in transit. However, once the encrypted mail lands on your correspondent's disk, it is unencrypted, making it vulnerable to the same sorts of problems discussed earlier.

I wish secure email were easier to use and more interoperable. In a study I did for a private client, I found all sorts of problems when different products were used to communicate. That is subject for another Web Informant, although if you are interested in seeing the results you can go learn more about S/MIME and PGP products.

This is probably more information than you bargained for, but it just shows that while paranoia is nice, getting a solid understanding of the technology behind your email is essential before you too become another email poster child. It would be nice if someone invented a product that would deal with all of these issues, and where you could just dial in a particular policy setting for your Notes or Exchange server and let it take care of the housekeeping. But until then, happy cleaning!

Self-promotions dep't

Okay, no more book promotions - promise. In the meantime, go here if you want to read some of my recent columns on Fawcette's Web Builder site.

David Strom
+1 (516) 944-3407
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