Ever tried to send an elephant through the Postal Service? (Attachments Are Evil…)

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(The following was originally posted in January of 2005 — with additional comments and resources added by popular demand. -Dan)

That’s what many computer users are guilty of when they try to leverage the internet email system to transfer large files that are far too bulky to be squeezed through plumbing that simply wasn’t designed to handle that type of load.

Most technicians get frustrated by this scenario because they can’t understand why people would do such a thing. Here’s the business-honest truth:

1) Email is familiar. Most users keep their email client open at all times, and it’s quicker to Alt-Tab (or Command-Tab) over to it than to launch a shortcut or bookmark pointing to another application, network location, or site.

2) Contact information in users’ email client is ready-at-hand; but seldom does it include a working hyperlink to an FTP site or designated upload directory on a contact’s company network or web site.

3) Most users are not even aware that there are other methods of file transfer; the ‘file-attachment-in-email’ model is ubiquitous and might only be challenged by a rival solution when a user finds that this method doesn’t get the job done.

To combat this mentality, some IT departments will restrict attachments in email altogether; most will at the least limit the size of attachments that leave their server. A clear majority of mailboxes are limited in size to protect the server from becoming top-heavy (running out of free-space on a hard drive is a quick way to see what happens in your organization when a server goes down).

So assuming your users are average, most are happily humming along, sending dozens of email attachments a day to all points outward — and until something ‘breaks’ (in other words, until the user experiences ‘unexpected behavior’), the status quo will remain unchallenged and your email server will be slow and unweildy.

Like the proverbial cow chewing its cud, messages will eventually get to their intended destinations; but it may take a while and with multiple attempts.

Are there some ‘best-practices’ tips that can be provided to users that will help moooooooove things along? You betcha!

A) The First Law is this: ‘Attachments Are Evil: Just Because You Can, Doesn’t Mean You Should’.

I’ve seen people carefully craft a one-page document in Microsoft Word, choose an appropriate (or not) font, set their margins to taste, copy-and-paste a company logo, and run spell-check twice before saving the document. Then they’ll make it an attachment to an email message that has no more detail than, “please see the information in this attached Word document.”

Let’s examine the logic here:

A.1) Your email client probably has font, spell-check, and graphics capability.

A.2) An attachment to email usually can’t be read by recipients catching their incoming mail on a wireless device (like a BlackBerry or PalmOS-based unit).

A.3) You have no way of knowing (usually) whether the recipient even uses Microsoft Word.

A.4) You just used TWO applications to craft and send a one-page document; when ONE would have been easier, faster, and wouldn’t have meant storing the document in two different places (the Word file on your hard drive, and the identical information in your ‘Sent Items’ folder).

B) The Second Law is this: ‘Attachments Are Evil: Size Matters’.

As important an issue as file size is in every-day computer use, most users do not know how to check the size of a file, nor do they understand how important this awareness is. Tech-Support centers regularly get calls from people who are trying to shove an 80-megabyte PowerPoint presentation through Microsoft Outlook, and intend to complain that the company email system is at fault.

Here are the facts that are not self-evident to most non-technicians:

B.1) When an document is ‘attached’ to an email message, it usually increases in size by 40-50%. This is because email can only include text; images, Word and PowerPoint documents must be converted to an industry-standard format (MIME) that can be tacked on the end of the message as a stream of text. Your email client does this for you; but the trade-off is that the stream of text is even larger than the original file.

B.2) If you attempt to email an attachment to an individual who’s mailbox doesn’t have enough free space to receive your file, it won’t even matter that you were able to squeeze it past your own postmaster.

B.3) Beginning with Microsoft Office XP, users can compress and optimize the raster images (JPG, BMP, TIF, etc.) contained in Microsoft Office documents (namely, PowerPoint and Word) so that they are as small as possible without sacrificing quality. Example documents we tested let us slim down a 200-megabyte PowerPoint document to less than 2 megabytes.

B.4) Microsoft Office will let users import EPS images (often used for logos and complex diagrams); but Office applications do not always store these very efficiently. Take a look at how large your Microsoft document is before and after the import; if it balloons from 5 megabytes to 23, you might try importing the same image in a different format (JPG or WMF?)… get some help from an Adobe Illustrator user if you don’t have the software to do this yourself.

C) The Third Law is this: ‘Attachments Are Evil: Content First, Format Much Later…’

Many business PC users get wrapped up in the nifty bells and whistles available in Microsoft Office and competing suites. People who get so connected to a certain look-and-feel of ‘fully-formatted’ documents will balk at the idea that they are paying more attention to detail and dressing than actual communication… but that’s the human tendency.

Here are the facts that may help keep us grounded:

C.1) Actual business was conducted — successfully — before graphics and fonts could be included in word processing documents, email, and wireless transmissions.

C.2) Using bells and whistles to add glitz to a document may set it up to fail at the other end — if the recipient doesn’t have the same software, fonts, display resolution, media player, or computing platform you do.

C.3) If you can imagine sending a richly-formatted email to 30 people, and 3 out of the 30 will be reading it in an email client with fewer (or incompatible) formatting features from your own, you will have lost the chance to communicate clearly to 10% of your audience. If you have to, format your own email client so that you create your message in ‘plain text’ format to begin with. If your message stands up as a professional communication in plain text, you won’t have any reason to soil it with a Tammy-Fae makeup job, will you?

D) The Fourth Law is this: ‘Attachments Are Just Plain Evil’.

Having beaten this like the dead horse* that it is, understand that there is indeed a place for Evil in the world. Just don’t make it your standard to default to Evil practices, and your friends and business associates may someday start to believe in the professionalism you aspire to.

Here are a fistful of vendors who will let you deposit a large file in a web-based form, and notify a friend or business associate where to go to retrieve that file:

arunasend.com (100Mb max)
bigupload.com (500Mb max)
driveway.com (2000Mb max, plugin available to send batches from desktop)
filewind.com (500Mb max)
MailBigFile.com (100Mb max)
MegaUpload.com (500Mb max)
MyTempDir.com (100Mb max)
QuickSharin.com (500Mb max)
TransferBigFiles.com (1000Mb max)
Uploading.com (300Mb max)
YouSendIt.com (100Mb max)

(*My favorite quote of all time is from Jack Benny, when he said, “What’s the use of beating a dead horse; except for the pure joy of it?”)

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