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The Practical Mac

Mail Trouble A-Brewin'

- 2003.05.06 - Tip Jar

A problem with Apple's Mail program has been brewing for several weeks. Specifically, the problem lies with attachments sent to users on other (non-Mac) platforms. The attachments usually go through without a hitch, and the recipient can open them without a problem. But sometimes they don't, and therein lies the problem.

This is one of those issues that the IT department absolutely hates to hear about - the infamous "intermittent problem." If you give us a problem that always happens at the same time, when you do the same thing, or in the same way, we can fix it. But those ghost-in-the-machine, "well it didn't do it this time," "it only happens sometimes" problems drive us crazy.

I wonder if Apple feels the same way, because that is exactly what they have on their hands.

I have been following this on the Apple Support Forum as well as some third-party boards for a couple of months. I was unable to duplicate the problem, and it had never happened to me, as far as I knew. Then one day I received replies to two emails, both recipients asking me to resend the email because they could not open the attachment (in this case a Microsoft Word document, though it also happened with an Adobe PDF file). I resent it. They still could not open it. I resent it using Entourage. Now they could open the attachment.

I would be curious to find out if this is a situation that happens all of the time on some of computers. If that is the case, it could be duplicated and diagnosed. Unfortunately, neither of the two recipients who could not open my attachment are anything more than business associates. If I could find someone I knew personally who had this problem with Mail attachments, I could trade some email with them and hopefully narrow down the scope of the problem.

I first started seeing posts on this problem back in February. Apple, through the Forum, has admitted the problem, although alleging it also happens with other email programs and even on other platforms. I have never had this problem with Entourage, Outlook Express, or Eudora (the only other Mac email programs I have used extensively). [Editor's note: No problems with Claris Emailer or PowerMail 3 either.] However, I do recall having a similar issue with a Windows email client (of course, the name escapes me now) several years ago. It turned out to be a problem with the way the program encoded and compressed attachments.

This issue can be duplicated in Entourage. Create an email with an attachment. Change encoding from "Apple Double" to anything else and change compression to anything other than "none." Send it to enough users, and sooner or later this very issue will rear its ugly head.

As of this morning, I have reluctantly switched to Entourage as my every day email program. While this has fixed my most pressing problem, it has created a number of others. If Entourage can be made to use the Apple Address Book, I can't figure out how. I have found some third-party utilities to sync the Apple and Entourage address books, but this is cumbersome.

I have also lost use of Apple's fantastic spam filter. Once again, my inbox is full of mail from get-rich quick schemes, pornographers, online casinos, and medical practitioners offering to increase the size of every imaginable body part.

Have you had this same problem? Are you able to narrow it to certain recipients and/or file types? Let me hear from you. Maybe we can help track down the ghost in this machine together. I will report back when we know something more.

Right now, I have to go. The former Nigerian Minister of Finance needs my help with an "urgent matter."

Steve Watkins is the Vice President for Information Technology for a mid-sized bank and also an attorney. He has been a Mac user for about ten years. He has owned some PCs along the way - but always came back to the Mac. If you find Steve's's articles helpful, please consider making a donation to his tip jar.

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