Why iPhone 2.0 won't yet rule the enterprise roost

The 13 key omissions Apple must fix before it can really compete with BlackBerry and Treo

Most of the world, it seemed, drank the Steve Jobs Kool-Aid about the new iPhone being a BlackBerry killer when the Apple CEO first announced the device earlier this year. But after nearly two weeks with the new iPhone 2.0 software on my iPod Touch, I can tell you that Apple has not yet delivered on that promise.

Don't get me wrong: The iPod Touch was the first PDA since my decade-old Handspring Visor that had a good enough user interface and capabilities to get my own money spent on it. And I'm addicted to using it on the train, having mapped out the unsecured Wi-Fi hot spots where I can do e-mail and other work during my commute. It's been a long time since a device has so enthralled me.

But despite being under that spell, I still see that Apple hasn't delivered what large businesses really need in a smartphone, despite its many amazing innovations thus far. That's actually the issue: Many of the misses are bread-and-butter ones that should have been there at the beginning, and certainly in the first explicitly business-oriented model. And, yes, its main competitors -- the Research in Motion BlackBerry; the Palm Treo, and even the Windows Mobile devices -- don't do everything below, either. But they do most of it, and Apple should be a leader, not a follower, in these business features, just as it is in the Web and user experience side of the equation. (Has anyone noticed how cool the new Calculator app is? Hint: Rotate it.)

Where Apple missed the boat on iPhone 2.0

Here's a baker's dozen of what's missing, done wrong, or done in a half-baked way. Individuals and many smaller businesses can probably adopt the iPhone despite them, but not larger companies or those for which security is important (such as hospitals, government agencies, and financial services providers). You already know all the legitimately good iPhone stuff from the ton of gushing reviews, so no need to repeat that here.

For more takes on what Apple needs to do in the next generation of the iPhone, check out the MacJury online radio panel that Jeff Garnet, Chuck Joiner, Chuck La Tournous, Terry White, and I participated in earlier this week. Some of the issues below came from these panelists, and the show covers others, such as better integration between e-mails and contacts.

If we're lucky, we'll see these in iPhone 2.1, not iPhone 3.0.

1. Voice dialing. In this day of hands-free-while-driving laws, how can the iPhone not support voice commands for the phone features? The user interface is great, but it still shouldn't be used when driving. (And why not voice commands for other items such as calendar entries? OK, that may require Mac OS X Snow Leopard.)

2. Attachment saving. I can save image attachments to the Photos folder, so why I can't I save other attachments such as Word and Excel files? Having to find the e-mail to which they are attached each time I want to refer to them is lame.

2.5. Oh, and why can't I open RTF files? RTF is the lingua franca word processing format used by many apps, including Apple's. The iPhone should support it, not just Apple's and Microsoft's proprietary formats. (And if Apple wants to attract lawyers, it should support WordPerfect format as well, although that could be a third-party app opportunity.)

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3. Primitive calendar support, part 1. I can sync to Exchange's public calendar, or I can sync to my computer's personal calendar (iCal, in my case), but not both. I don't put my personal business on the company's shared calendar, so I need to be able to sync to both. Sure, iCal has my Exchange appointments, but when I'm traveling or commuting and don't have my computer with me, if I sync with iCal (as I do), I can't get any updates from Exchange wirelessly. I can sort of get around that if I get an e-mail invitation from Exchange -- accepting the invitation puts it in my iPod Touch's calendar -- but that's really a workaround.

4. Primitive calendar support, part 2. Like many execs, I have some standing meetings that are every three weeks or the on fifth of the month. But iPhone doesn't support those -- yet Exchange does. Clearly, the iPhone's vaunted Exchange support isn't complete.

5. Primitive calendar support, part 3. As my colleague Tom Yager notes in his iPhone 3G review, you can't send out invitations from a calendar item you create on the iPhone, even though it's exactly the kind of thing a mobile user would expect to be able to do.

6. No ability to synchronize to-do notes or tasks. You can enter to-do items in the iPhone, but you can't sync them to your computer or to Exchange. And your task list from Exchange isn't visible to the iPhone. Again, what about that vaunted Exchange support?

7. Primitive security. It's great that you can now do remote kills of an iPhone, and thank you for supporting Cisco VPNs and Exchange access controls, and I'm perfectly OK that Apple makes you buy a Mac server to run that management software (IT departments could use more Macs in their lives). But the use of a four-digit numeric PIN as the first line of defense is pathetic. And why isn't the on-device data encrypted? This is standard in the competing platforms.

8. No keyboard option. I could never get the feel for the BlackBerry keyboard, but thousands of users love it. Apple (or a third party, but I think this is too key for delegating) should offer a keyboard attachment that offers the BlackBerry-style input for those who want it. Apple sells a Bluetooth charger, after all, so why not this?

8.5 Hey, and add a microphone while you're at it for the iPod Touch. The Touch is the perfect device on which to record notes, do VoIP in Wi-Fi range, or just "tape" podcasts. Griffin's iTalk device would do the trick, except it mysteriously does not work on the iPhone or iPod Touch, just the older iPods that can't connect wirelessly. (Hmmm!)

9. No ability to add comments. I love being able to see rich attachments in a meeting or follow along a budget conversation with the Excel spreadsheet in front of me. But imagine how much better that would be if I could add sticky notes to those files so when I get back to my office I have more context on what we discussed. (Switching to the Notes app is a poor substitute.)

10. No cut and paste. An iPhone is not quite a computer, but it's darn close. So why can't I cut and paste text among apps? A common issue is getting a malformed Web address in an e-mail, so you can't click it. If I could copy and paste it into Safari, I could then correct it and get to the desired page. I'd also like to cut and paste between e-mails and notes, or between e-mails and my contacts list. And hey, my decade-old, screen-scratched Handspring Visor can copy and paste.

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11. No native support for Notes or Groupwise. Yes, Exchange is the big gorilla in the world of enterprise messaging and collaboration, but a sizable minority of the world does not use Microsoft's systems. For example, I know a large California county government that would adopt iPhones and iPod Touches, except that there isn't any  GroupWise support. Thus, they can't enforce their security and access standards, which they can with most other PDAs and smartphones. Apple shouldn't have stopped with Exchange in building in core enterprise messaging support.

12. Poor e-mail account switching. If you have multiple e-mail accounts (and who doesn't?), it's great that the iPhone lets you access them all, keeping their e-mails separate. But switching among them is a pain; you have to go all the way back to the root of the mail app to switch. There's got to be an easier way to switch e-mail accounts at any time, such as through a pop-up menu.

13. Ability to work with multiple e-mails. Because the iPhone doesn't block spam e-mails, I get a lot of them on my POP account (Exchange does the work for me on my corporate e-mail). While I like the quick-delete swipe feature in my e-mail list, why can't I multiple-select e-mails to delete the trash, or move them to the same folder, or mark them all read?

Where Apple should lead

There also a few areas that are crying out for a better way, that Apple could and should pioneer given its mastery of user experience.

Enhanced time zone support. Here's something everyone could do better, so Apple, please take the lead. Like many people, I schedule calls with people all over the United States, Canada, and Europe -- and sometimes other countries. It's hard when entering an appointment to get the time zone right, especially for those time zones I don't deal with often (such as Atlantic time for Puerto Rico and New Brunswick, or whatever time zones Alaska and Hawaii are in). Sure, I could change the default time zone for the iPhone using Apple's Settings app, but that changes everything and forces me to tell the other party to hang on a minute. I'd like an unobtrusive option to change the time zone of a specific appointment as I enter it, so the iPhone can figure what local time it is for me.

Wi-Fi printing. More and more printers are wireless, and when you're on the road, it would be great to be able to print your notes, contacts, map, or whatever to one of them.

Other issues that affect everyone

There are a few other things I'm not sure are enterprise-specific but are annoyances nonetheless. So here goes:

First, my iPod Touch often is slower in switching among apps than it used to be now that I have the 2.0 software installed; a few times I thought the iPhone crashed after waiting 10 or more seconds for something to happen. I've heard others with similar problems, all those who upgraded pre-3G devices.

Second, syncing apps when you have multiple computers is tricky. Some third-party apps disappear when you sync on the second computer, and reappear when you later sync on the first. Others never disappear. Yes, I disabled the sync function on the second computer's iTunes, but it mysteriously re-enables itself, so I often forget to disable it again.

Third, Apple no longer includes a dock with the iPhone, and its expansion connector has changed, so not all previous peripherals fit. Bad Apple! That type of incompatibility is just not necessary, especially when some of these Bluetooth chargers come with US$100-plus earpieces.

Fourth, if you're going to put a camera in a smartphone, why wouldn't you support the sending of those pictures over the cellular network via MMS? The iPhone does not.

Fifth, can't Apple and Adobe figure out a way to support Flash on the iPhone? Flash files can be resource hogs, and badly implemented ones can cause crashes (ask any Firefox user), but these are so prevalent on the Web and so much a part of rich Internet content that it's nuts not to support them in a device as rich-Internet-focused as the iPhone. Ditto with Java support.

Finally, I wish the iPhone could store passwords, so when I go to a hot spot, for example, I wouldn't have to re-enter all that information each time. While I'm fairly proficient with the touch keyboard, it's still a pain to expand the Web page to be able to find the fields I need to complete to log in.

(For those of you wondering why I don't have an original or 3G iPhone: As much as I would like an iPhone 3G, I'm not willing to shell out nearly $1,000 per year for the service, which is what it would cost for me to shift from my current cell carrier, whose family plan I'm enmeshed in and can't get out of because other family members live in areas where AT&T's coverage sucks. So an iPhone would be a wholly new, additional plan. Fortunately, I've discovered that since I'm not a road warrior, I am perfectly happy having a regular cell phone in one pocket and the Wi-Fi-capable iPod Touch in another. Most of the time, anyhow.)