The iPhone as a mail device

Apple has been getting a ton of press about the launch of v2.0 of the iPhone software (along with the iPhone 3G, of course!) I’ve been using a pre-release version of the v2.0 firmware on my iPhone, but I didn’t want to write about it until the release because I hoped that some of the glaring problems with Apple’s implementation would be fixed in the RTM version. Sadly, this doesn’t seem to be the case.

Apple has a page with lots of deeper information on the enterprise features of the v2 software. I haven’t spent any time with the device management or provisioning bits, nor the VPN support. However, I have spent a lot of time with the Exchange-compatible features, and overall I’d have to say Apple isn’t there yet. Windows Mobile still has some compelling features that the iPhone lacks. It’s entirely possible that I’ve just missed some iPhone features; I’ll update this post as I learn more (or am corrected).

Update 1: [0017 Monday 7/15] I should point out that Exchange ActiveSync is a protocol that supports lots of different content types and protocol option. Apple, like most other EAS licensees, has implemented a subset of EAS. I’m complaining about Apple’s implementation here, not EAS itself.

About the author

Before I get into the meat of my piece, a few words about my qualifications. I’ve been a Mac user since 1984, an iPhone user since July 8th of last year, and an Exchange admin since 1995. I’m a Microsoft MVP for Exchange and Office Communications Server. My day job involves every possible sort of exploration into how Exchange works, with a heavy focus on mobility. I carry a Windows Mobile 6.1 device daily and rely on it to get my work done. I’ve been in love with the polish and responsiveness of the iPhone UI from day 1. It’s an awesome device for most purposes. However, from my standpoint as an experienced Exchange administrator and WM device wrangler, there are still a lot of missing pieces (or things that are poorly implemented).


Let’s start with e-mail, which seems like an easy enough application to implement. Apple got the single biggest item right: push e-mail works properly. Mail arrives when it’s supposed to, and replies are sent like they’re supposed to be. HTML mail displays beautifully. In fact, the overall Mail experience is basically just like it was in v1, for better or worse.

We interrupt this review for a special gripe: Apple, why on earth do you expand the ENTIRE folder list when I want to navigate to a new folder or move a message? This is incredibly inefficient for large mailboxes. It would help a great deal if the Mail application would remember the most recently used folder and jump to it, or (even better) if the folder list were collapsible. Please fix this in the next point release. (Side gripe: why can’t I flick left or right to change e-mail accounts, like I can with Safari’s page selector?) We now resume our regular programming.

You might think that the iPhone would work well as an offline mail client. You might also think that you should be dating Danica Patrick and that gas should be $1.25/gallon. Bad news: the iPhone’s offline story is poor. When the device radios are off, any attempt to move or delete messages results in an error dialog. How lame is that? Did anyone at Apple test a Windows Mobile device to see how it works in this situation? There are a few nice touches, though. For example, a small status line in the main mail view shows you how many messages are queued for sending. At least the software is smart enough to automatically attempt a sync as soon as the network comes back up.

There are a number of other Windows Mobile 6 features missing here: for instance, you cannot flag or unflag messages for follow-up; you can’t set out of office messages or timings, and the device will frequently complain if you try to throw away a message that a client- or server-side junk filter has already moved elsewhere. The extremely convenient press-and-hold shortcuts that WM provides (like “d” to delete or “m” for move) are of course absent here, too.

Bottom line: mail is prettier on the iPhone. The devices are tied in terms of sync behavior and performance. My WM 6.1 device has a significant edge in usability speed because of one-handed message selection and movement, plus the press-and-hold keys. I realize that for novice users this speed differential might be much smaller… but I’m not a novice. (And, to forestall any flames: the iPhone keyboard is OK with me. Once I got used to it, it’s as fast as a physical keyboard.)


OK, so let me get this out in the open: I can’t stand iCal on the desktop. It’s so lame compared to Entourage, Outlook, and OWA that I just flat don’t use it. The fact that the iPhone’s calendar app emulates iCal closely is not a good thing. Color coding of events on the iPhone is driven by where events appear in iCal, meaning that if you sync with Exchange (or Entourage, FTM), your events appear in one color. There’s no support for Exchange categories, an obvious omission.

One thing I do like: the default behavior when a new meeting invite appears is to play the calendar reminder sound and show an alert. This is useful because there’s no other way to show that you have pending meeting invites. There’s a host of weird behavior involving existing recurring events; after your first sync, most of them will show up as “maybe” (which in Apple-speak means “tentative”), even if you’ve previously accepted them.

Now, on to the really bad stuff. There are several common– nay, fundamental— things that you cannot do with the iPhone calendar application. You cannot:

  • create a meeting request and invite other people to attend. Without this, the wireless calendar functionality is largely useless unless you’re the Unabomber or some other kind of Luddite hermit who never works with others. (Oddly, you can view the attendee status of meetings you create on the desktop!)
  • create a recurring meeting unless it is repeated daily, weekly, bi-weekly, monthly, or yearly. That’s right– no more “first Thursday of every month” or “every Monday, Wednesday, Friday” appointments. This is disgraceful. Even Palm managed to eventually get this right, for crying out loud.
  • create a meeting in a time zone other than the one you are currently in. I guess you might be able to do this by changing the device time zone, but that doesn’t seem like a very good idea to me, and I haven’t tried it. I have tried (in vain) explaining why I created a meeting request for 4:30am Pacific time because I forgot my device was still on Eastern time, though.
  • view suggested meeting times or free/busy times, either for your own calendar or for others’. That makes sense, given that you can’t invite other people, but it’s still super lame.
  • move to an arbitrary date, in either the future or the past. Say you want to check your schedule for 331 days from now so you can grab some frequent-flyer tickets to Maui. Hit the “month” button, then flick until you get to June 2009. Let’s hope you don’t need to look at dates in the far future or you’ll end up with a pulled tendon or something.

As with the offline mode behavior of the mail app, it’s mind-boggling that Apple didn’t get these right. We’re not talking cutting-edge functionality here. The fourth one is especially egregious because it’s been that way since the v1.0 release.

Special note to IMAP users: you can receive meeting invitations as .ics attachments, but you can’t open them or add them to your calendar. This is apparently a feature, not a bug. You’re welcome. (Special bonus: the Calendar app just died on me as I was looking at my list of pending invitations).


The iPhone doesn’t include a built-in tasks/to-do application. Windows Mobile 6 has task support baked in, so it has a clear advantage here. Apple missed the boat here, as this is a natural piece of functionality for a mobile device. There are a number of such programs at the iPhone App Store, but none of them seem to support wireless sync. My money is on OmniGroup’s OmniFocus, which I’ve recently started using on the desktop. OK, I admit it; OmniFocus doesn’t support sync yet either, but it’s supposed to soon, and I trust them based on their track record.


The iPhone Notes application is anemic and, IMHO, basically useless. (No, I don’t mean the iPhone version of Lotus Notes, because it doesn’t exist; I mean the built-in Notes application). Given its overall level of uselessness, it’s no surprise that it doesn’t sync with Exchange-side note items. If server sync is important to you, get Evernote, which has clients for Mac OS X, iPhone, Windows, Windows Mobile, and IE/Firefox/Safari. (Ping me if you want an invite). [Update 2: I use OneNote on my Windows machines, and its sync behavior with Windows Mobile is brilliant: plug in your device, automatically get the client, and then sync “just works”. It is not, however, wireless, which is what I need. Plus, there’s no Mac client.]

Policy control and security

The first time I synced the iPhone with my home Exchange server, I didn’t see two things that I expected. Windows Mobile correctly warns me that I’m using a potentially untrusted certificate, because it’s issued by my self-signed root CA. Once the initial sync connection was made, I got a warning that I would have to accept the organization’s EAS policy to let sync continue. The iPhone didn’t show either of this warnings. I consider this a failure in both cases. Without a certificate validity warning, an attacker could easily mount a man-in-the-middle SSL attack. Accepting the server-side EAS policy without telling the user opens the risk that the user’s device will be remotely wiped without her knowledge, or that other policy changes will unexpectedly remove device functionality. Because I’m on the road, I haven’t actually tested any of the remote wipe or security policy options because I need the device to keep working until I return home. Look for a follow-up article (in which I will probably complain that the iPhone doesn’t support the most interesting new EAS policies of Exchange 2007) later.

As a side note, I fixed the original WM certificate error by adding my domain root CA certificate to the device. There doesn’t seem to be a way to do this on the iPhone, although I haven’t tested the desktop provisioning utility.


Are there bugs? Yes, in fact there are. The most noticeable one for me is Apple’s refusal to use IMAP EXPUNGE to properly remove items. This makes it very frustrating to use an iPhone for IMAP access to an account that you use with Outlook or Entourage elsewhere. There are other bugs, too. For example, when you “reply all” to a message, your sending address is included as a recipient. I already mentioned the way that previously-accepted repeating events act, but I am too busy/lazy to come up with a detailed repro case.

Where to learn more

Apple’s got a decent “quick start” page explaining how to set up Exchange ActiveSync for use with the iPhone, and the Exchange team has a more detailed post on the Exchange team blog. I suspect the comments for this post will be a fertile ground for updates, too. [Update 3 @ 1944 7/15: my main main Omar has a wiki that chronicles bugs in the iPhone Exchange integration here.]


Filed under Reviews, UC&C

27 responses to “The iPhone as a mail device

  1. Liam Colvin

    Excellent post – this was the summation of the features I was looking for and couldn’t seem to find anywhere else.

  2. Hi, Paul –
    I just want to say thanks for such a detailed and balanced article, and I also want to give you a heads up that we’re featuring a link to your blog over at our new MS discussion forum focused on mobility: the Windows Mobile Connection. Please stop by, and feel free to sign up – we’d love to see you there.
    Bill, Admin/Moderator

  3. Now I’m really glad I don’t want one.

  4. A review at its best giving a clear depiction what to expect with the email silution.

  5. Rick

    I’m coming off of windows mobile as well. I agree with your findings. I’m hoping apple comes through on adding features. It took windows mobile to get to version 5 before they started to get it right. The iPhone interface is so good that I’m willing to sacrifice and adapt until they get it right.

  6. JMastera

    This question has been asked multiple times across multiple sites but I don’t seem to get the answer (full answer) I am looking for.
    I have a user that would like to use the exchange feature. He is curretnly using MobileMe (formerly .mac) for his Contacts, Calendar and Email. On first sync, will the iPhone allow for you to choose which direction you want the overwrite to go? I want to make sure the the users MobileMe Calendar and Contacts push to the Exchange instead of a blank Calendar and Contacts file to be written to the phone. Email is not a concern as he would rather have his company email on the phone, but he works out of his personal calendar and contacts way too much to not have them.

  7. Kerry

    I think you are wrong about the self-signed root CA exposure (in the Policy control and security section). When we setup our iPhones we DID get a warning and had to accept our untrusted self-signed root CA.

  8. Dave

    One more gripe for enterprise users: No apparent ability to look up people in the Company Directory. Fine if you have a few hundred employees and can load the whole list on your PC, but what if you have thousands? Or hundreds of thousands!

  9. milles21

    Unfortunately Dave, I believe you are incorrect you can look up the Company directory. Go to contacts on the main screen > click groups > it will take you to a screen that allows you to look up Company Directory.

  10. milles21

    Unfortunately Dave, I believe you are incorrect you can look up the Company directory. Go to contacts on the main screen > click groups > it will take you to a screen that allows you to look up Company Directory.

  11. Brian

    …even with all these flaws…
    The first time I seen it in action, I decided to dump my WinMo phone immediately. I have a iPhone on order…see you later Windows Mobile.

  12. Ryan

    I’m coming from WM as well and my phone used to store emails up to a certain period of time. The iPhone lets me choose 50, 100, 200 “recent emails”. Is there a way for it to keep emails for 1 week, 2 weeks or for a distinct period of time? For instance it now only has emails back to Monday (this is Thursday) and has way under the 200 emails I’m telling it to keep.

  13. Steve

    You also cannot do a simple selection of text to do a copy/paste/replace. Pretty annoying.

  14. Karan M

    Great write-up.
    Regarding the reply-all including the sender, make sure the email address you used to setup EAS on the iPhone is the primary SMTP on Exchange and you shouldn’t see youreself included in reply-all.

  15. sysengr

    Any thoughts on the security and privacy side of the data that gets left on the iPhone or the device management yet? This can’t even be considered as a corporate email device until the features are at least as good as Mobile 6.1 finaly delivered.

  16. Paul Robichaux

    Thanks for your comment! I have *lots* of thoughts on this subject, but I haven’t gotten around to writing them down yet 🙂 Look for a future article that digs into this subject some more once I’ve gotten more time with Apple’s provisioning tools.

  17. MSbug

    Somehow, I have not been able to configure exchange on my iphone 3g. Does my exchange admin need to do anything on the exchange server?
    When the iphone tries to validate my exchange account using the server information I provde, it gives me a certificate error. After I click ‘Accept’ on the error, it says account has been validated, but I cannot see any e-mails, contacts or calendar.

  18. Bill Calle

    I’m coming off of several years of WinMo usage and overall love the iPhone. I waited until 2.0 in hopes of getting good Exchange integration after frustration with 1.0 and 3rd party sync solutions. While I am not ready to give up on the iPhone just yet (crossing my fingers that 2.1 or subsequent versions fix my gripes), I think there are enough gaping holes in this implementation to make this worthless as an enterprise device. The calendaring in particular is fatally flawed. The most annoying issue in my mind is the complete lack of integration with respect to recurring appointments. Setup a recurring appointment (let’s say every Monday) then change next weeks specific instance to take place on Tuesday. What does the iPhone show? Two meetings, one on Monday and one on Tuesday! AARRGGHH. Equally upsetting is the lack of category support (I’d have hoped that this would have tied into the color coding the way it does in Outlook) and the fact that it loses all notion of how my meeting time should show up (free, busy, tentative, out of office, etc. are completely disregarded). Lastly, I often add custom notes to meetings I’m invited to that I used to be able to lookup on my WinMo device (striving for a paperless office). What happens on the iPhone? Sometimes it works, sometimes it doesn’t and instead shows only the original information. AARRGGHH!!!!

  19. “(No, I don’t mean the iPhone version of Lotus Notes, because it doesn’t exist; I mean the built-in Notes application)” – I think you will find that IBM realized the relative lack of readiness for enterprise class apps on the iPhone ans instead opted for a browser based interaction, something the iPhone excels at…
    Due out next month.

  20. Dave C.

    Thank you for the very informative article. Do you know if any of these issues/gripes are addressed in the latest 2.0.1 update?

  21. Paul Robichaux

    Dave, I haven’t seen a list of bug fixes in 2.0.1 yet. I can say that in my limited testing, 2.0.1 doesn’t seem to fix any of these bugs.

  22. Julia

    The Company Directory issue is not resolved so simply. For example, we happen to keep our Company Directory in a public Contacts folder in Outlook. That’s a no-go on the iPhone; can’t access public folders. We then looked at moving it to the GAL, populating the phone information, etc., only to be told that, yes, you would then be able to SEE it via the iPhone…but the data there is untouchable. In other words, you can SEE my phone number, but you can’t tap it to dial.
    So, really, how does that help anything?
    Another issue I’ve encountered, in addition to all those listed in this great review, include the nagging fact that, if I reply to a message using the iPhone, my desktop Outlook client doesn’t reflect that I’ve done so. Not cool.
    And, lastly, I am unable to send a “high importance” message (or low importance for that matter) using the iPhone…and, perhaps even worse, if someone sends a high importance message to me, there is no indicator onscreen that the message is high importance.
    Some of the things that have troubled me have been dismissed by my peers in the IT Department as “advanced” features that “no one” cares about…but, to me, the lack of some of these things seem rather “basic” to me rather than “advanced” and it feels like amateur hour to me.

  23. Heath

    Just wanted to warn users about your suggestion to use Evernote for syncing notes. Check this out from their Terms of Service:
    “By submitting, posting or displaying Content in Public notebooks in or through the Service, you give Evernote a perpetual, irrevocable, worldwide, royalty-free and non-exclusive license to reproduce, adapt, modify, translate, publish, publicly perform, publicly display and distribute such Content. You also agree that Evernote has the right to elect not to accept, post, store, display, publish or transmit any Content in our sole discretion. You agree that this license includes a right for Evernote to make such Content available to other companies, organizations or individuals with which Evernote has relationships for the provision of related services, and to use such Content in connection with the provision of those services.�

  24. Carole Fisher

    I work for a law firm – one of our attys just purchased the 3G —
    having significant trouble with this unit –
    however of most importance — he cannot receive email via the Exchange server – unless his office laptop is logged into the network.
    I have worked with Apple to no avail –
    any suggestions? If so – please email me at

  25. Todd B.

    Is there anyone besides me who hates the behavior of email headers on Reply and Forward… it shows “on at wrote: … I can’t stand it. Plus it makes it obvious others that you are out of the office sending mail from the iPhone instead of from Outlook. Anyone know of plans to make that configurable so it can just use the From/To/Subject header instead?

  26. Nala Rillak

    Apple has now issued V3.o of the iPhone S/W. My questions:
    – Have any of the problems discussed here been fixed?
    – If so, which ones?

  27. Nala, please see — I think that will answer most of your questions 🙂