Making Microsoft products play nice together
I recently recommended MS Office 2003 Small Business Edition to a customer for his new laptop. There are several reasons why I did not recommend Office 2007 but I’ll save that for another time. He took my advice and, since he paid for it, he wanted to use as many of the programs as he could. Everyone in his office uses Outlook Express but he was now using Outlook. A couple days in, it was noticed, that certain attachments were not getting to recipients in the office – the ones using Outlook Express. The email would come through and so would some attachments but, for the attachments that were gone, there was never any indication that they even existed in the first place. These were standard graphics files, mind you, nothing fancy. Well, after going around for a bit with Microsoft (a bit = 1 week, or so), the problem was traced to the ISP email server.
Outlook and Exchange encode certain attachments in a manner that are stripped when processed by “improperly configured” email servers – namely Open Source ones. That seemed a little odd to me that the ISP was to blame for the attachments disappearing between two Microsoft products, so I tested it. I sent a few emails from Outlook to Outlook Express through our Open Source mail server – no problems, everything got where it was supposed to go. I then disabled support in our MTA for TNEF encoding – that, according to Microsoft, was the culprit, and sure enough, the attachments that weren’t working for my customer stopped working for me. Apparently, the ISP did have their server mis-configured.
Transport Neutral Encapsulation Format, or TNEF is, paradoxically, a proprietary attachment format used in Outlook and Exchange – there really is nothing neutral about it. Our company MTA was compiled with TNEF decoding so there were no problems passing these attachments to the recipients. Since it is unlikely for an ISP to rebuild it’s mail servers, TNEF related issues can be largely avoided by sending email as HTML of plain text. Avoid RTF in Outlook as this format uses TNEF while HTML and plain text use the standard MIME encoding. TNEF encoding can sometimes contain user login names, file paths, and other potentially sensitive information from which attack vectors could be derived. This vulnerability was patched in 2006 but there are certainly a large number of un-patched systems out there.
Eventually, my customer grudgingly went back to using Outlook Express, accusing the entire IT industry of being a racket, since the large cable company that provides their internet service was not interested in reconfiguring their mail servers, I advised him to buy a product that didn’t work with this mis-configured equipment, Microsoft, the biggest software company in the world, couldn’t get two of it’s flagship products to play nice with each other. Microsoft did offer free support hours to quell my irritation with them, demanding that they make their products work with each other. I declined because, as a Microsoft Partner, we get free critical support – and I only call them when it’s critical. I did get a really nice golf shirt with the Microsoft logo emblazoned on the sleeve though. I believe that Microsoft sent my customer a credit for future purchase, but he never got it. It was sent as an attachment.
