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iPhone Help: Troubleshooting the top five enterprise problems

When enterprise users need help with their iPhones, IT is charged with troubleshooting their shiny toys. Here's how.

With the launch of the 3G iPhone on July 11, many users will undoubtedly want to bring the device into your environment and, like it or not, you may have to help support it.

"If you have a BlackBerry and you have problems, IT is going to be in charge of that," said Avi Greengart, research director with Current Analysis. "If you have an iPhone or a laptop or a desktop, the company is providing it and needs to make sure it works."

The good news, Greengart said, is that the iPhone is generally simple to repair and has become more enterprise-ready as Apple broadens its scope. "With the coming update, it's becoming viable for enterprises that couldn't even support it before, let alone handle manageability," he said.

With that potential influx in mind, we've assembled a guide for some of the most common problems today, while others (Exchange email, remote wipe) will soon have solutions when the iPhone 2.0 software becomes available Friday. Have a problem not covered? Send it in and we'll do our best to find a solution.

1. How can I charge my company for an iPhone?

Assuming that the iPhone has already been approved for corporate use (we can't help you otherwise, sorry!), AT&T has a page explaining how to activate and get reimbursed for iPhone purchases, if applicable.

If your company generally distributes mobile phones to employees, the iPhone is no different and everything should be done through IT. If your company reimburses you for phone costs, go to the AT&T store, starting July 11, with your corporate account contract number and your device will be activated in store. Sources: AT&T, Gizmodo

2. How can I give away my iPhone without giving away all my data?

Apple thought of almost everything they could to make sure users have a great iPhone experience … until they want to resell or refurbish it. A few months ago, security researcher Jonathan Zdziarski reported that a toolkit he published was being used to pull deleted data off refurbished iPhones after they came back from the Apple store.

Data ranging from sensitive financial information to Facebook updates was recovered, and as your users weigh trading in their 2G for a 3G iPhone, it's important to make sure they know the risks ... and how to mitigate them.

While Zdziarski recommends jailbreaking (which breaks Apple's device restrictions and allows you to install custom software) your iPhone and doing some midlevel hacking, security researcher Rich Mogull developed a simpler method to wipe iPhone data:

After restoring the iPhone in iTunes, unselect all the sensitive data you want wiped under the iTunes "Info" tab. Now, create a playlist the size of your iPhone's hard drive and sync, making sure the storage bar at the bottom looks full afterwards. Unselect that playlist and repeat twice, with two different playlists.

Mogull warns that this method isn't fully tested, but it should be enough to prevent "casual recovery."

On July 11, however, this all should get much simpler. Apple Insider reports that iPhone version 2 software includes a complete device wipe option that avoids all of these steps, so it might be simpler (and secure) to upgrade the iPhone's software performing this workaround. For those who want to upgrade from 2G to 3G on Day 1, however, this option is still handy. Sources: , Securosis

3. How do I un-brick or un-jailbreak my iPhone?

Technically, it shouldn't be your problem when the boss's nephew "jailbreaks" his iPhone to let him run a few unauthorized applications, but when the device suddenly stops working, or when he wants to wipe it to get the official 2.0 upgrade in a few days, you'll probably be called to save the day.

There are several methods floating around on the Internet, but many have the potential to permanently disable Bluetooth or other features, so we recommend going by Apple's instructions first:

  1. Make sure you're using a computer with the latest iTunes installation (7.5 or later).
  2. With the device disconnected, hold the top power/sleep button until a red slider appears, indicating that you can power down the device.
  3. Press the bottom home button while reconnecting your device to the computer. Continue holding the home button.
  4. A dialog box saying "Connect to iTunes" will appear, and you can release the home button and walk through the on-screen instructions.

NOTE: While any contacts, music, and other data will be wiped off the device, iTunes should have most of that data backed up and ready to go as soon as the device is finished syncing. Sources: Apple Support

4. My iPhone is broken. Fix it.

Though not a technical question, breakage -- support staff report -- is still a common problem. If the solution isn't obvious and you don't have a trained iPhone technician on staff (not surprising, since there aren't certifications outside Apple's internal workings at the moment), your best bet might be to avoid hours of frustration and drop the problem in Apple's lap with AppleCare. Each iPhone comes with a year of hardware repair coverage and two years of phone technical support, and the year of hardware coverage can be doubled with the purchase of AppleCare for the phone.

Hacking your phone or dropping it from a ledge might very well void this coverage, but many other day-to-day problems are covered, and Apple's customer support is known for going out of its way to make things right quickly.

Do note that this isn't the same as insurance, which still isn't offered for the iPhone, so if you have users who just aren't good at keeping devices alive for more than a month or so, perhaps the iPhone isn't the right fit for them. Sources: Apple Store, ITKnowledge Exchange

5. How do I get Exchange push email?

With the iPhone 2.0 software, the iPhone will begin supporting Microsoft Exchange ActiveSync and push email, contacts, calendaring and more. Apple has a PDF checklist guiding IT managers through what they will need and how to deploy, but note that the iPhone's ActiveSync support only includes Exchange Server 2003 SP 2 and Exchange Server 2007. If those don't work for your enterprise, you can always deploy IMAP, which has many, but not all, of the features (MS Exchange Team has an ActiveSync/IMAP comparison).

If you still have security or usability concerns, a host of third parties like Syncronica offer workarounds to help provide access without compromising security.

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