Earlier this week, InfoWorld reported that “Apple lied” about the secure mail functions of its original and 3G iPhones. While that claim could be argued, you’d be going too far to agree with the article that says the iPhone has now betrayed business users.

Encryption of e-mail is the issue here. Microsoft Exchange mail servers, used in so many corporations and large companies, insist on encrypted mail when they deliver your messages. They don’t double-check your assurance, however. The trouble stems from more than Apple’s previous iPhones. Exchange will apparently believe anything that a mobile mail program tells it about messages.

That’s not new behavior from Microsoft engineering, but Apple took advantage of it ever since it released the 3.0 version of its iPhone software. 3.0 was touted as being ready to swap mail with Exchange. All the software was doing was claiming to send and receive messages with encryption. Only the newest 3GS iPhones can actually do this. Apple’s done the right thing after mis-reporting security. So now the earlier iPhones can’t exchange secure mails if they’re updated to the 3.1 software.

It’s complicated, but the situation’s fallout isn’t as simple as the InfoWorld article claims. If your iPhone user is a corporate-level officer, like a VP of Sales, they’re going to insist on being able to read company mail over their iPhone — security be hanged. You just try to tell them they have to buy a new iPhone to do that. And there may be a good data for believing the iPhone has become a C-level officer’s tool. Microsoft might have to wear some of the egg on its face. Read the rest of this entry »