Apple is a great company with great products, and the stuff they do right is well known and documented by hordes of fanboys and fangirls. I am no disciple, but I do use and love Apple products. But as someone who is part of the Internet of Things intelligentsia, I must say they have made some missteps lately, and both of them are in areas squarely in our wheelhouse.
First let's talk about upgrading to iOS 5. Apple's servers strained under the load of the hordes downloading the updates on day one, and many were met with decidedly non-Applesque error messages related to the servers' inability to keep up. This made the updates fail in horrible ways, with little guidance to help recover. I evaded the server problems on day 3, but only got through the long painful iCloud-ification of my iPhone's backup thanks to a preflight review of the blogosphere. For 2 hours, while my iPhone was still tethered to my desktop and appeared updated, my apps were gone and continued to trickle down either over the USB cable or through iCloud. I could not tell which.
Then there's iCloud. It's an obvious evolution of the iDevice platform, and is deservedly greeted with frothing excitement by the Apple community. But it's not ready for prime time. As I researched how this was all supposed to work, all I found was Apple marketecture promises of photo streams syncing automatically, all my device data backed up and replicated for me automagically. Great, I thought. Now where do I configure all of these rules about where photos get sent, which updates, apps, and content to send to which of my devices. I have 7 iOS devices under my management. I don't want them all getting the same content. I need a management portal to keep all of this straight. The reality is, www.icloud.com ain't it, kids. At present, one needs to manually configure each device, and even then I am still really foggy about what happens, and when.
This is M2M - welcome to our world, Apple. Devices doing things automatically, communicating in the cloud and influencing people and other devices in real time. Except with iCloud, there's very little in the way of privacy or "solution" management for the end user.
M2M newb mistake #1: when millions of devices all need to check in to your server cloud, you better have surge-scaled that cloud appropriately and thought of all the ways things will go wrong and provide a rollback process when they do. This lesson is well understood by M2M practitioners and our customers - we don't have the luxury of having a technophile in front of devices. Software updates to M2M devices need to happen silently, automatically, and reliably. We have spent thousands of engineering days working on exactly this problem, because with M2M there is no user around to do something about this:

M2M newb mistake #2: users need to be in control and know they are orchestrating this wonderfully magic information synchronization. Simply saying "automatic and effortless" is not enough, even if that were the case. I know our customers would be more comfortable in hearing "secure, manageable, and automated". That's why our motto is "Connect, Manage, and Innovate". Don't forget the "manage" part - it's important.
Perhaps iCloud's new product manager may want to give us a call.
