The iPhone as a mail device, 3.0 edition

[ Updated on 23 June 2009 to fix a couple of mistakes and add a few new tidbits ]

Last summer I wrote a post about the utility of the iPhone 2.0 as an e-mail device for people, like me, who are heavy e-mail users. Now that the 3.0 release of the iPhone OS is upon us, I wanted to post an update to see what Apple’s fixed, or not, from the original complaints. I had hoped to get some hands-on time with a Palm Pre as well, but haven’t quite made it there yet. However, I have spent some time using the version of Outlook Mobile from Windows Mobile 6.5, so that’s now my baseline standard for comparison.

Executive summary: Apple invested a ton of time in the 3.0 release, but most of it went to other aspects of the OS, not into the messaging and calendaring experience.

Policy and account control

I didn’t spot any changes here. The big one I was hoping for was the ability to create and manage multiple Exchange ActiveSync accounts. Sadly, Apple didn’t include this. The extended policies in EAS version 12 (like forced disablement of the camera or Bluetooth) still aren’t supported. You still can’t install your own certificates, either.

[Update]: As Chris Haaker pointed out in the comments, you can indeed disable the camera using Exchange 2007 EAS; for a complete list of the policies 3.0 supports, see this doc at Apple’s site; and, of course, you can install your own certs by e-mailing them to the device, using the over-the-air configuration utility, or distributing profiles with the utility. In addition, Apple improved certificate support quite a bit: 3.0 adds the ability to provide client certs for authentication, and it now uses OCSP for checking certificate validity online instead of depending on static CRLs.

E-mail

In my initial review, I started with basic e-mail operations. These are essentially unchanged: the look and feel of the Mail application is identical to the 2.0 version for the most part. The annoying automatic expansion of EVERY SINGLE FOLDER YOU HAVE is still there. You still cannot delete messages while the iPhone is offline. Instead of fixing this issue, Apple has chosen to deactivate the “delete” icon on the message toolbar. However, when you’re in the message list view, you can still use the swipe-to-delete gesture, or the Edit button, to delete a message… and then you get the same error that the message can’t be moved to the trash. Fail.

You can queue replies or forwards while offline, which is a welcome improvement.

One area where Windows Mobile 6.5 really shines in comparison to the iPhone is in the new conversation view for e-mail. There are a number of other WM 6.5 mail improvements that I won’t cover here; suffice to say that the new Outlook Mobile extends Microsoft’s lead by providing a better pro-level e-mail experience than the iPhone 3.0 does. Apple could definitely improve things just by using the correct EAS verbs for reply and forward, though, which they still don’t do

Oh, that bug with not properly sending IMAP EXPUNGE commands to remove deleted messages: still there. I guess Apple thinks it’s a feature.

Calendar

If you didn’t like the iPhone 2.0 calendaring experience, you won’t find much to change your mind here. You can now create meeting invitations for your Exchange calendar (but not for your MobileMe calendar, a baffling omission given that MobileMe is marketed as a service useful for families). I am hopeful that the forthcoming Exchange support in Apple’s Snow Leopard OS will force Apple to make iCal more useful, and that those changes will ripple out to the iPhone. Until then, though, Windows Mobile still kills the iPhone in calendaring usability.

Speaking of usability: since my original review I found a few more annoyances:

  • meeting cancellation notices show up on your calendar as “Canceled:whatever“; there’s no way for you to use the cancellation notice to remove the event.
  • If you receive an invitation on the device, then accept it from the desktop or OWA, it will still show up in the calendar app as a pending invite until you try to open it.
  • You still can’t see .ics files that arrive in IMAP-connected Exchange accounts. Fortunately, Exchange 2010 includes an OWA link in meeting invites, so you can click the link to jump into OWA and accept the invitation there.

[Update] One nice addition that I forgot to mention: when you get an invitation, you can see where it falls on your calendar, and there’s a new disclosure chevron next to meetings you create that lets you view the status of the invitees (provided you’re using Exchange 2007).

IMG_0105.PNG IMG_0106.PNG  

Tasks

Nope. This is another promised Snow Leopard feature that will hopefully make an appearance on the iPhone at some point. In the meantime, I’ve been using imTasks, which works flawlessly with all of my Exchange accounts. I also tried TaskTask, which has a somewhat nicer interface but which hasn’t worked very well for me.

Contacts

Steve Foskett summarizes this better than I could. Bottom line: it’s like the Mac OS X Address Book in your pocket, with all the good and bad that entails. No support for contact public folders, no way to add a GAL contact to your own contact list, and a 100% chance of getting duplicates if you use Entourage + Sync Services to sync contacts to the device through MobileMe.

New iPhone 3GS features [UPDATE]

Apple says that the 3GS has “hardware encryption”. It’s not really clear exactly what this means. In the enterprise deployment guide, This blog entry suggests that remote wipe is so much faster on the 3GS because it’s essentially a decommissioning operation– erase the master encryption key for the device and you’ve effectively erased all its data. I haven’t seen any confirmation of that, though, and it’s not clear what other value there is to encrypting data on the device given that apps are sandboxed and there’s effectively no external storage. (You also can’t force encryption on with EAS, as you can on Windows Mobile).

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12 Comments

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12 responses to “The iPhone as a mail device, 3.0 edition

  1. Ty Young

    Hi Paul, have you observed any improvements in support for certificate-based authentication for Exchange ActiveSync ? Thanks for your great comments meanwhile.

  2. I can’t delete emails at all since I upgraded to 3.0, even if I am online. This is seriously broken. :-/

  3. Hey Paul – With regards to your section on Policy and Account Control – iPhone OS v3 now supports EAS 1.2 policies w\E2K7. They specifically call out ‘Allow Camera’ and ‘Password History’ but I have not dug in enough to see if they support all of them or just a subset. I am on E2K3 so I am not able to test it easily.
    I do see in their docs (http://www.apple.com/iphone/enterprise/integration.html) that they do support enterprise client certificates for 2Fa. We are looking forward to this for our iPhone users as well as the ability to now hardware encrypt if you have the 3Gs model.
    I have been very happy (okay it has only been a few days) with the new model so far. It is definitely faster …

  4. Jeff Beckham

    Another issue I’ve found with the iPhone 3.0 software is that even if you have a password timeout policy enforced form Exchange, the iPhone ignores the timeout value. We have a 10 minute timeout period, but I can go on the phone and change it to 1 hour. This prevents the device from complying with our security policies.

  5. Apple says that the 3GS has “hardware encryption”. It’s not really clear exactly what this means. In the enterprise deployment guide, This blog entry suggests that remote wipe is so much faster on the 3GS because it’s essentially a decommissioning operation– erase the master encryption key for the device and you’ve effectively erased all its data. I haven’t seen any confirmation of that, though, and it’s not clear what other value there is to encrypting data on the device given that apps are sandboxed and there’s effectively no external storage. (You also can’t force encryption on with EAS, as you can on Windows Mobile).

    You only get hardware encryption on the 3GS. It’s always on, there’s no “off” option. The previous versions weren’t fast enough to deal with hardware encryption, so there’s no option for it.

    One area where Windows Mobile 6.5 really shines in comparison to the iPhone is in the new conversation view for e-mail.

    Only if you use conversations. Some of this isn’t better or worse unless you use it. If you only sort by received date, or a non-conversation criteria, then the fact that the iPhone doesn’t have it is meaningless. If you care? Sure. If you don’t? Then who cares.

    There are a number of other WM 6.5 mail improvements that I won’t cover here; suffice to say that the new Outlook Mobile extends Microsoft’s lead by providing a better pro-level e-mail experience than the iPhone 3.0 does.

    1) Apple and the iPhone are not trying to be Outlook Mobile. EAS is a convenience feature for iPhone users, not a critical device criteria.
    2) Like what? Saying “oh, there’s a bunch of other stuff that WM 6.5 wins on” and then listing none of them gives no one the ability to get any useful data out of that statement.

    Apple could definitely improve things just by using the correct EAS verbs for reply and forward, though, which they still don’t do

    Examples? Again, without that kind of info, there’s not much useful in that statement.

    Until then, though, Windows Mobile still kills the iPhone in calendaring usability.

    In what way? Usability-as-aFeature list? Sure. Usability as actually using the apps? Doubtful. Windows Mobile has never been nice to use, and it still tries to substitute “features” for “usability”. Having set up both WM and iPhones to use EAS, I can tell you which UI is less insane by FAR. WM has all the usability of a schizophrenic duck.

    No support for contact public folders, no way to add a GAL contact to your own contact list, and a 100% chance of getting duplicates if you use Entourage + Sync Services to sync contacts to the device through MobileMe.

    If you mean “Dupes when you sync EAS and Mobile Me”, well yes, you will get dupes, because the Mobile Me is a completely separate contact list from the EAS contact list, which is completely separate from LDAP. Unless you want the iPhone to mangle the contact info and not show you all the info you have. There are ways to manage this a bit better, but if you have 3 contact syncs going on, and someone is in all three, then you’re going to have duplicates. That’s not a bug.
    If you mean “Dupes due to E’rage sync”, yes, but that’s not entirely Apple’s fault. Middle names still aren’t properly supported in Entourage, and if you have someone with an iChat/AIM account, but no Microsoft-approved IM account, then E’rage has no idea what to do with it. That’s not anyone’s fault but the Mac BU’s for being so shortsighted about what contact fields to support in a Mac product. As well, duplicates *are* manageable, but it still takes too much manual action.
    However, sync services issues are not solely fixable by Apple.

  6. Thanks for stopping by, John– I appreciate the feedback.

    I know what “hardware encryption” means, and I understand why it’s not on previous-gen devices. I’ll wait to see what else Apple says about the feature before I pass a final judgement.
    The iPhone, AFAICT, doesn’t let you change the sort order of messages at all, which is another beef I have. After using conversation view in Outlook 2010, OWA 2010, and WM 6.5, I find it indispensable, and it’s one of the features that I most commonly see people get excited about.
    Well, here’s the deal: EAS is not a “convenience feature” for heavy e-mail users. Apple’s implementation is better than Palm’s, but it’s still got some shortcomings. As to what’s in WM6.5 that’s missing from the iPhone, here’s a short list:

    proper support for inline voice mail messages recorded by Exchange Unified Messaging
    the ability to see free/busy time for users when you create a meeting invite
    a shared nickname cache between OWA, Outlook, and WM, so that you get consistent addressing behavior and views across all three
    SMS sync, so that SMS messages on the phone appear in your e-mail inbox and can be searched, filtered, flagged, and so on just like regular messages
    There are separate verbs for “reply/forward” and “smart reply/forward”. The “smart” version only sends the reply/forward text to the server, and the server appends the original message so that you don’t have to download it and then immediately re-upload it. Apple was using the wrong verbs

    Calendaring: the iPhone doesn’t show free/busy, it doesn’t suggest meeting times, it doesn’t allow click-to-call in phone numbers in the location field, it doesn’t properly handle cancellation messages… the list goes on. It’s not so much a question of missing features, though there are plenty of those– but many of the features Apple did implement don’t work right! For example, why can you click-to-call in Safari, Mail, etc, but not in the calendar app?
    Give me some credit here, John :) I understand that if I put the same person in two different data stores they’ll appear twice on the phone. However, if I put Joe Blow in MobileMe and then the next day I see ten copies of his contact record, that’s a problem, and I routinely see that. I haven’t tried to pin down the problem to Entourage or Sync Services or MobileMe or moon phases. I don’t know and don’t care. It Should Just Work.

  7. Todd Booher

    Hey Jeff,
    You can get around this issue by creating a policy using the iPhone Configuration Utility and sending that policy to the device via email. We use this in conjunction with our server policy to lock down the device. It’s not ideal but seems to be the only way to remove that option from the UI. Not sure why it’s not removed if you have the idle timeout set to 15min in the EAS policy.
    Todd

  8. Paul,

    Well, here’s the deal: EAS is not a “convenience feature” for heavy e-mail users.

    EAS is not there for “heavy email users”. I’ll put my IMAP traffic up against anyone’s EAS traffic any day. EAS is for people who need specific functionality on their phone, either because they use Exchange as their email server, they use an EAS-compatible email server (Kerio, Communigate, etc.), and they want better integration. However, Exchange is not the sole source of heavy email use, no matter what the ExPR people say.

    proper support for inline voice mail messages recorded by Exchange Unified Messaging

    If you’re not using Exchange as your EAS source, this is a complete non-issue, and one thing you have to keep in mind is that the iPhone audience does not map 1:1 with the WM audience. WM is designed to be used with Exchange. Any other functionality is a convenience, and based on how craptacular dealing with non-Ex email services is on WM, it shows.
    The iPhone cannot treat non-Ex EAS implementations like an afterthought. So the fact that it doesn’t support an Ex-only feature doesn’t surprise me at all, and for my users, is a non-issue. For Exchange users, it sucks, but that’s an implementation detail. Using WM sans Ex is not a happy walk in the park either, but non-Ex is not a priority for that team.

    the ability to see free/busy time for users when you create a meeting invite

    Agreed. That is annoying, and kinda stupid.

    a shared nickname cache between OWA, Outlook, and WM, so that you get consistent addressing behavior and views across all three

    I doubt you’ll ever see this. Apple is not going to do that kind of work for MS client software, again, being a 100% EAS client, and going feature-for-feature with WM is not a design goal for the iPhone, and thank god for that. I think you need to reset your expectations here a bit. I highly, HIGHLY doubt the iPhone will be a full-on 100% feature compatible replacement for WM in an Exchange shop. But, if you have an iPhone, the EAS improvements make it easier to get work done.

    SMS sync, so that SMS messages on the phone appear in your e-mail inbox and can be searched, filtered, flagged, and so on just like regular messages

    Then they kind of stop being SMS messages, and are just short emails. I can almost see why you’d want this, but I can’t see why it should be a major design goal for the iPhone. It’s kind of a ‘meh’ feature, especially if you’re on an EAS server that isn’t Exchange, something far more common with the iPhone user base, (the people definitely giving Apple money), than the WM user base, (People who MIGHT give Apple money.)

    Calendaring: the iPhone doesn’t show free/busy, it doesn’t suggest meeting times, it doesn’t allow click-to-call in phone numbers in the location field, it doesn’t properly handle cancellation messages… the list goes on. It’s not so much a question of missing features, though there are plenty of those– but many of the features Apple did implement don’t work right! For example, why can you click-to-call in Safari, Mail, etc, but not in the calendar app?

    Some of that I agree with, in particular the free/busy issue. However, if you put the phone number in the notes field, you get click to call.
    I don’t know why that’s field specific, because I can’t see what difference it makes, but yeah, put the number in the notes field.

    I don’t know and don’t care. It Should Just Work.

    Okay, so now that you’re being specific here, yeah, I can’t argue that Sync Services has way too many issues. Unfortunately, that’s still too client-dependent. It’s particularly bad with calendaring, but then again, cross-client calendaring sucks period. (Categories in Outlook and Entourage for the easy example)
    Hopefully, Snow, and the next version of Entourage will smooth this out. Sigh.

  9. Chad Conrow

    One problem we’ve observed with iPhone 3.0 is that when someone accepts a meeting from the phone, it sends it from the first name in the to: field for the meeting request, and not the person accepting the meeting on the iPhone. This causes funny things like distribution lists “accepting” meetings, wrong users in responses, etc, and creates confusion… Here’s hoping they fix it in 3.1…
    One thing that Apple does have going for it is that the 2 year old hardware is getting the OS update, even if some features are missing. Windows Mobile is notorious for not keeping up to date on any given device. Go to the T-Mobile store and buy their currently on the shelf Dash and it only runs Windows Mobile 6.0 (no WM 6.1 update available at all unless you want to trust the homebrew hackers) and is considered a “legacy” device by T-Mobile…

  10. 118 blogs for OCS/UC (and counting)

    Looking for information on OCS or UC? The @DrRez Twitter team (http://twitter.com/DrRez) pulled this…

  11. Ed

    I hate iphones. They are a toy with no practical use over a blackberry. They don’t work properly with Exchange 2003 or Exchange 2007. The OWA side is fine, but the Exchange account just will not set up.
    We have a BES which works fine. Our Blackberry users are on Exchange 2003. All other mail users are on Exchange 2007. we changed from having a front end server to having our OWA published through our ISA server. Everything works for anything with a Web interface (including the iphone) but the Exchange setup on the iphone won’t work anymore, with the new server’s details.
    There seems to be no simple guide which doesn’t have something along the lines of “connect to the server that everyone connects their mobile devices to – your IT people will have the details” written in it.
    As an aside:
    Apple users are so bloody smug about their gadgets and how IT staff are so thick if they can’t get them to work. The fact that they don’t work simply is just another cross we IT people at the coal face have to bear from the Steve Jobs house of pain. People buy stuff and expect us to be able to get it to work in two minutes, or we are substandard in some way.
    I hate everything Apple have ever produced – the iphone doubly so. Mainly becasue it is senior people who keep bullying me into making the damned things work when they don’t do ANYTHING properly.
    Rant over.

  12. More things Apple needs to fix for Exchange e-mail on the iPhone

    Via Twitter, I found this post pointing out 3 things Apple needs to fix to make its Exchange e-mail client more useful, from the perspective of a BlackBerry user. Their selections: flagging messages for follow-up. Yes! Jump scrolling to the…