Previous 1 2 3 4 5 6 Next 123 Replies Latest reply: Jan 7, 2010 7:54 AM by JRB2 Go to original post
  • klamerus Level 1 Level 1 (0 points)
    The lack of understanding of Outlook vs. Exchange and encrypted communications vs. encrypted files in this thread is appalling.

    Outlook is the product on a user's desktop with which an iPhone synchronizes (just like other mobile phones and devices). The iPhone does not directly synchronize with an Exchange server. The default Exchange server to Outlook client protocol is proprietary and there are no products on the market that synchronize with Exchange directly. There are a very limited number of enterprises that enable any of the alternative protocols.

    For whatever reason, Apple has not taken this seriously enough and currently (at least with 3.0 and earlier) cannot sync with Outlook when there are > 1 Outlook profiles available on a user's system.

    The current issue is that the specification to require encrypted off-line storage (OST or PST) is actually being enforced first with with 3.1 which only works on the latest batch of iPhones. It failed to honor this request with earlier iPhone OSes, but this version does - which doesn't work on earlier iPhones and so the whole thing falls ashambles.
  • cardsdoc Level 1 Level 1 (0 points)
    Any way to know in advance if your exchange system requires device encryption? My wife and I both rely on our hospital email on our iphones. I upgraded without issue as I have a 3GS, but my wife has a 3G and if I upgrade her phone and her email doesn't work, I'm in big trouble. I know I can ask our IT helpdesk but they don't always know what they're talking about.
  • GreggTeHennepe Level 1 Level 1 (0 points)
    klamerus, your description of iPhone integration with Exchange is incorrect.

    The iPhone syncs directly with Exchange via ActiveSync, it has nothing to do with Outlook (or Entourage). The encryption that is being enforced in 3.1 is encryption of the iPhone itself (not the communication, which is already encrypted), and that's only if it's required via ActiveSync by Exchange policy. Only the 3GS iPhone can do this, thanks to on-board hardware encryption.

    See for details.
  • GreggTeHennepe Level 1 Level 1 (0 points)
    cardsdoc, the iPhone configuration utility allows you to capture console logs from the iPhone, but I haven't mucked with it and don't know if it will show you the AS policies coming from the server.

    On the other hand, it is relatively trivial for an Exchange admin to discover whether the "Require Encryption" policy box is checked for mobile devices.
  • GreggTeHennepe Level 1 Level 1 (0 points)
    I should note that my earlier post was incomplete, the iPhone Enterprise Deployment Guide indicates that in addition to iPhone 3GS, latest generation iPod Touches 32GB and larger also support device encryption.
  • Kamih Level 1 Level 1 (0 points)
    My wife and I both have 3GS and until now have been syncing with exchange wireless just fine. We just both upgraded to 3.1 and although our contact and emails still sync well, our calendar is missing a lot of the data. It seems like it's syncing most of the recurrent events, but not the rest of the appointments. But even for the recurrent events it's pretty random. We've rebooted the phone, turned off and on calendar and even had our IT people work on it for about half a day on Friday but still no luck
  • klamerus Level 1 Level 1 (0 points)
    If my understanding of how the iPhone synchronizes with "Outlook" is incorrect, then how is it that I can (and have) synchronized with Outlook when I'm unconnected to Exchange.

    There is no published API for synchronizing directly with Exchange. I'm sorry.
  • klamerus Level 1 Level 1 (0 points)
    I've also repeatedly said (maybe elsewhere) that this is not an issue of messaging or communications encryption.
  • klamerus Level 1 Level 1 (0 points)
    Other than IMap and the like.
  • Level 1 Level 1 (0 points)
    It's because OS 3.1 fixes a security hole which Apple left open to rush the Exchange support with iPhone 3G. If you company is using encryption on the exchange servers your iPhone 3G will not be able to connect.

    This is a HUGE problem Apple has pushed out. They originally said support for Exchange (which I've been using for the past 2 years now) and now its been taken away. very bad. If they do not fix this within 3 months, I am ditching the iPhone.
  • acb123 Level 1 Level 1 (0 points)
    Also get message: The connection to the server failed.

    Deleted account and re-booted but neither helped.

    Message was edited by: acb123
  • who@hk Level 1 Level 1 (0 points)
    Same here. Error message refers to encryption no longer available. I think it has something to do with the SSL setting. Help! I am using safari to access company webmail in the mean time but it just takes so much longer to do the same thing...
  • GreggTeHennepe Level 1 Level 1 (0 points)
    klamerus, I think you're refering to the ability of iTunes to sync with a local Outlook/Outlook Express install via USB. That's a different situation than syncing wirelessly with Exchange. As far as I know the ActiveSync issue should not impact a sync with a local Outlook installation, as ActiveSync isn't involved.
  • Basseq Level 1 Level 1 (0 points)
    Klamerus: Per Apple, "iPhone communicates directly with your Microsoft Exchange Server via Microsoft Exchange ActiveSync (EAS), enabling push email, calendar, and contacts." (

    I'd also be interested in a method to remotely check the EAS policies active for mobile devices (e.g., without having access to the Exchange server).
  • JRB2 Level 1 Level 1 (0 points)
    I am afraid Apple is using the iphone 3.1 upgrade as a way to limit the number of customers that will be using MMS when it comes out. In other words if you do not upgrade to 3.1 you will not be able to use MMS. A lot of customers will not upgrade because they do not want to lose Exchange email, thereby limiting the number of customers that will have MMS available. I hope this is not true, but since Apple has not announced that they will 'fix' the Exchange problem it makes me wonder!
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