Getting ActiveSync going seamlessly internally and externally

Discussion in 'Windows Small Business Server' started by Milhouse Van Houten, Sep 18, 2009.

  1. What single URL can I use for ActiveSync (iPhone) that would work locally as
    well as outside of the office?

    In an Apple doc entitled "iPhone in Business Microsoft Exchange," there's
    this, which I think is key:

    "Make sure the DNS for your network returns a single, externally-routable
    address to the Exchange ActiveSync server for both intranet and Internet
    clients. This is required so the device can use the same IP address for
    communicating with the server when both types of connections are active."

    That doesn't entirely make sense to me (same IP address?), but I get the
    point, I think.

    So, externally (our OWA address, with an example domain):

    But that doesn't work internally, of course. This would:

    But that doesn't work externally, obviously.

    How do I specifically modify DNS to resolve this so that
    "" can be used everywhere? I think
    "" somehow needs to be aliased internally with the word "server"
    in DNS, but who knows.

    SBS 2003 R2

    Milhouse Van Houten, Sep 18, 2009
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  2. Milhouse Van Houten

    Paul Shapiro Guest

    If your internal domain is myDomain.local and the external domain is, you can make your sbs server the authoritative DNS for Then you can create an A record for your
    that specifies the same internal IP address as server.myDomain.local. Since
    your internal DNS server now sees itself as authoritative for the domain, you also have to create and maintain any other DNS records that might ever be needed by internal users. So the
    rest of the world still sees the external DNS server as authoritative for and gets DNS records just like they do today. But your internal
    users are getting all DNS records for from your SBS server, so
    you have to keep the duplicate records as needed.
    Paul Shapiro, Sep 18, 2009
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  3. To add to Paul's solution, which will work for you, I think that the doc is
    saying that if you connect internally using WIFI, that internally you would
    need the zone created to match the external records, but using the internal
    IP address, which Paul stated. However, if you simply do not connect using
    WIFI, then you won't have a problem because it's going through the external
    cellular system anyway.


    This posting is provided "AS-IS" with no warranties or guarantees and
    confers no rights.

    Please reply back to the newsgroup or forum for collaboration benefit among
    responding engineers, and to help others benefit from your resolution.

    Ace Fekay, MCT, MCTS Exchange, MCSE, MCSA 2003 & 2000, MCSA Messaging
    Microsoft Certified Trainer

    For urgent issues, please contact Microsoft PSS directly. Please check for regional support phone numbers.
    Ace Fekay [MCT], Sep 18, 2009
  4. That did the trick. I was very close earlier but enough off for it not to
    work. It also didn't work until I flushed DNS. Thanks.

    And thank to Ace as well for pointing out the Wifi/Cell aspect (I actually
    don't know which is used), which hadn't occurred to me.

    Now, I only hope that another point in the Apple PDF doesn't undermine the
    whole effort: "For all firewalls and network appliances, set the Idle
    Session Timeout to 30 minutes. For information about heartbeat and timeout
    intervals, refer to the Microsoft Exchange
    documentation at"

    I'm not aware of any such thing as Idle Session/Connection Timeout on our
    router. One of the linked articles mentions that it's a timeout relative to
    the port (443). Don't have that either to my knowledge, but I'll look into
    Milhouse Van Houten, Sep 18, 2009
  5. Don't worry about those settings. I haven't had to touch them, even if they
    did exist, in any installation with iPhones or Windows Mobile phones. If you
    have any user's handhelds that do show issues with not updating or grabbing
    emails as they are received, or even when manually selecting ActiveSync,
    then we can address that when needed.

    I haven't read the iPhone docs, but when the first iPhone was handed to me
    to test it for the company I was assigned to, it instantly connected. We
    already had Windows Mobiles and some old Pocket PCs, which were all in use,
    so the iPhone worked nicely. The only issue is ATT's network and the
    principles using them complaining about connectivity, which is a discussion
    left for another time.

    And glad I was helpful by making you aware of Wifi vs cellular. :)

    Ace Fekay [MCT], Sep 18, 2009
  6. Milhouse Van Houten


    Nov 12, 2012
    Likes Received:
    DNS for iPhones

    You can add a fully qualified DNS zone to your internal server and leave the domain hosted as is. For example if your iPhone needs to collect from, on your internal server, set up a new dns zone called (so not with an A record for mail). In the new zone (which should not allow any dynamic updates) create a new A record but do not type a host name, just put your internal mail servers ip. Now, when you connect to the wireless or intranet, will resolve to your internal mail server ip and when you connect externally (which should then use external dns servers) it should resolve to the external IP. I have been using thi method for a couple of years now and don't get any resolution related issues.
    keithfount, Nov 12, 2012
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