Dear Mr. Internet:
When I use e-mail to send attached files my recipients sometimes either can not open them or don't receive them at all.  How can I make sure that the files I want to send always get through and can be opened?

Jim Bellow
RE/MAX Realty Group
Atlanta, GA

Without a doubt, e-mail is still one of the most powerful online tools we have at our disposal.  And, its ability to help us send digital files is part of that power.  However, because it was originally designed for text messaging only, there are some quirks to how various e-mail systems handle attached files.

When using e-mail to send attached files, there are only two issues to consider:

1. Will the recipient receive the attached file?;

2. If so, can they open it?

There are ways to send attached files so that the answer to both of these questions is always a resounding "yes!"  However, we will look at each issue independently since, depending upon your particular circumstances, the approach may be different.

Neither Sleet, Nor Rain, Nor Snow...

There are several reasons why someone may not be able to receive your attached file.  They are:

• Too Large and/or Too Many - most e-mail systems choke on large attached files or too many sent at the same time.  A good rule of thumb is to avoid sending attachments that are over 1MB in size or more than three files together;
• Not Allowed - because of ever-expanding threat of viruses, many e-mail systems will not allow certain types of files sent as attachments (e.g. executable files - .exe).  In fact, some of your clients and prospects that give you their work e-mail address may not be able to receive any kind of attachment due to their company security policies.

There is an easy and affordable solution to both instances above and it involves avoiding the use of e-mail attachments all together.  Whalemail is a US $7.95/mo service (as of this writing) that allows you to deliver any number of files of any size (up to 100MB) to anyone who has access to the Web. 

This is the way it works.  Once you create an account and log into Whalemail, you are given 100MB of temporary file storage space on their server.  You simply upload the files you want to send via your Web browser (by just clicking a couple of buttons) and then have Whalemail send a simple text message to your recipients that includes a link to where they can download those files via their Web browser.  This simple process completely circumvents all the file delivery issues associated with e-mail attachments.  Also, recipients don't have to have a Whalemail account or log in to receive the files which makes it very convenient for them.

While getting the file there is one thing, making sure it is readable by your recipient is another issue all together...

Opening A Can Of Worms

If you use e-mail to send attached files, your recipient may not be able to view them for one of the following reasons:

• File Data Is Scrambled - when you send an attached file, e-mail systems "encode" purely digital data into a text file so it can be sent over standard e-mail systems (remember, e-mail was originally designed only for text messaging).  If your recipient uses a different kind of encoding scheme than you, then they will not be able to open your attached files.  This happens frequently with corporate e-mail systems;
• Doesn't Have Appropriate Software - if your recipient does not have the same software you used to create the file, they will unlikely be able to open it.

The first issue above is easily handled by Whalemail since it does not change the file in any way when uploading or downloading via the Web.  The second one can be handled by creating a PDF version of the file using Adobe Acrobat.  PDF (Portable Document Format) files are universally viewable files that most people can view with the free Adobe Acrobat reader.

The only fly in this ointment is that the Acrobat software necessary to create PDF files can be pricey (several hundred US dollars).  A much less expensive alternative is PDFMailer (currently about US $49) which does a good job of creating PDF files quickly and easily -- though it does not have the extensive extra features that the more expensive Adobe Acrobat software offers.

The least expensive option (i.e. free) for creating universally viewable files is one of my all time favorites: eFax Messenger Plus.  Like Acrobat, it creates universally viewable files that are typically much smaller than the original.  However, it requires the recipient to download and install (just one time) the free eFax viewer to read these files --something that most clients and prospects are not likely to do.  This leaves the PDF option as the surest way to go.

However, just because you create files that are universally viewable, it doesn't mean they will arrive that way.  Remember, many e-mail systems will scramble your attached files, even PDFs if they use a different encoding scheme than you.  In that instance you would again use Whalemail to send your PDF or eFax files so they retain their integrity.

The ability to almost instantly send any kind of file directly to any person on the planet with an Internet connection is easily one of the most powerful benefits of using the Net.  Being aware of the limitations and how to get around them not only makes your life easier, it will impress your clients and prospects too --and that is another kind of power we could all use more of!

(NOTE: Mr. Internet, his company and staff receive no compensation whatsoever from any third party vendors or service providers. Investigate any products or services found on the Net thoroughly to your satisfaction before using them at your own risk.)