This blog post is probably out of date. If you want to set up Exchange ActiveSync, you should instead consult one my guides:
	iPhone Exchange ActiveSync Setup		iPad Exchange ActiveSync Setup
	iPhone ActiveSync Troubleshooting		iPad ActiveSync Troubleshooting

That's right: I now have five Exchange ActiveSync accounts on my iPhone!

Among the many exciting features of Apple’s version-4 iPhone OS is the long-awaited ability to sync to multiple Exchange ActiveSync servers. The new software, now dubbed iOS 4, can synchronize mail, contacts, and calendars between many different services that use Microsoft’s Exchange ActiveSync protocol, including Microsoft Exchange 2003, 2007, and 2010 and Google’s Gmail service.

Who Needs Multiple Exchange Servers?

You may be wondering if you need this capability. After all, only business people commonly use Microsoft’s corporate Exchange email server, and they tend to only have a single account. But Microsoft’s Exchange ActiveSync protocol is widespread: It is supported by Google Gmail, Microsoft Live Hotmail, and many other services. Contrary to expectations, most people actually do have an Exchange ActiveSync account, and many have more than one!

I currently use no less than five Exchange ActiveSync accounts, and I’m very pleased to have all of them successfully synchronized with my iPhone. I use Google’s Gmail service for personal mail as well as two Google Apps domains (GestaltIT.com and Fosketts.net). I also have two genuine Microsoft Exchange server accounts belonging to corporate clients. It’s amazing to have all of these up and running on the iPhone!

How To Set Up Multiple Exchange ActiveSync Accounts

Setting up a Google account as Exchange instead of IMAP brings additional functionality

It’s really quite simple to set up multiple Exchange ActiveSync accounts in iOS 4: You just do it. Where the old iPhone OS would complain if you tried to enter a second Exchange ActiveSync account, iOS 4 happily accepts them. It’s not clear what the limit is: I set up five Exchange accounts and see no limit in sight!

Refer to my iPhone Exchange ActiveSync Guide for step-by-step instructions on setting up Exchange ActiveSync on the iPhone. I’ve also put together an iPad Exchange ActiveSync Guide.

Note that many folks, like me, had already added their extra Gmail and Exchange accounts as IMAP, since the old iPhone OS had no trouble with these. In this case, you should disable these accounts first to avoid trouble. I decided to turn off my old IMAP accounts rather than deleting them, just in case I needed to fall back to this method in the future.

Look at that! A unified inbox! But why all those other inboxes?

Note that iOS 4 also includes two long-awaited features: A unified inbox and threaded message view. These work great with multiple Exchange ActiveSync accounts, allowing quick access to all your messages.

Quirks and Bugs

Apple seems to have used an incorrect (too short) Exchange server timeout. If you are running iOS 4.0, you should install the Exchange timeout profile (per Apple TS3398) by clicking here from the iPhone and rebooting.

Although iOS 4 mail is much nicer, it’s far from perfect. Most importantly, all this only works on iOS 4 compatible hardware: The iPhone 3G, 3GS, and 4. The original iPhone has to stick with 3.0 and its single-Exchange limit.

Apple may have added a unified inbox, but they made the mail app list even more cluttered by listing everything three times: Once in the unified inbox, again with a line-item per account inbox, and a third time per-account. Odd.

By default, every Exchange account added is named “Exchange” rather than using the email address like other account types. This is ugly, and requires the user to manually change the account name in Settings->Mail to avoid confusion.

It took a while for the Calendar app to synchronize, and it used incorrect calendar names for a while. Also, it seems to only synchronize the default calendar, not any others you might have.

iOS 4 will happily maintain duplicate contacts in one or more lists. I synchronized Address Book with Gmail and Entourage, so all of my contacts were listed four times. It’s probably best to synchronize only one contact list to avoid this situation.

Pay no mind: You won't lose all your Exchange contacts, just those from this account!

When you turn off contact synchronization, iOS 4 pops up a disturbing warning that “all Exchange contacts will be removed.” They won’t. It will only delete the contacts from that one Exchange ActiveSync account.

© sfoskett for Stephen Foskett, Pack Rat, 2010. | How To Set Up Multiple Exchange ActiveSync Accounts in iPhone iOS 4
This post was categorized as Apple, Everything, Features, Personal. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

Considering the high profile Exchange enjoys in the iPhone details page and the exhaustive list of supported mail servers on the iPad page, the absence of Exchange was notable. I wondered aloud if perhaps Apple would release a corporate option pack with Exchange ActiveSync, VPN, and other enterprise features.

Yes, the iPad supports Microsoft Exchange ActiveSync

Happily, this appears not to be the case. Apple updated the iPad site contents while announcing pre-ordering of the device, and Microsoft Exchange is now included. This is a relief – I suspect many would be very disappointed if they couldn’t use their new toy at work!

VPN support still is not listed anywhere on the iPad site, however. But since my fear of an enterprise option doesn’t look to be coming true, I’m going out on a limb and suggesting that this will be in the package on April 3 as well.

© sfoskett for Stephen Foskett, Pack Rat, 2010. | Yes, the iPad Supports Microsoft Exchange
This post was categorized as Apple. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

This blog post is probably out of date. If you want to set up Exchange ActiveSync, you should instead consult one my guides:
	iPhone Exchange ActiveSync Setup		iPad Exchange ActiveSync Setup
	iPhone ActiveSync Troubleshooting		iPad ActiveSync Troubleshooting

Is your non-3GS iPhone locked out of your Exchange 2007 ActiveSync server after upgrading to iPhone OS 3.1? It’s a feature, not a bug! Here’s how to get older iPhones up and running with Exchange Server 2007 SP1!

What’s The Problem?

Microsoft Exchange Server 2007 SP1 added a feature to require mobile ActiveSync devices to encrypt data, enhancing security. Before iPhone OS 3.1, all iPhones incorrectly told the Exchange server that they supported on-device encryption. This allowed all iPhone hardware to function with Exchange 2007 SP1 servers that required device encryption. But original and 3G iPhones do not support device encryption, undermining corporate security policies.

The iPhone 3GS hardware actually does support device encryption, and iPhone OS 3.1 correctly reports this capability. But iPhone OS 3.1 also (correctly) reports that earlier hardware (the original iPhone and the iPhone 3G) does not support device encryption, so some Exchange 2007 SP1 servers refuse to allow them to connect. Oops!

What’s The Solution?

There are four possible solutions, three of which require IT assistance. Your Exchange administrator can research the meaning and implications of these options:

1. Disabling device encryption allows all iPhones to connect, but does not force any Exchange ActiveSync device to encrypt data. This is not a great solution from a security perspective, so don’t bother trying to convince IT to implement it!
2. Allowing non-provisionable devices enables all iPhones to connect but weakens security in general, allowing each device to enforce or ignore policies. This is a slightly better solution, since encrypting devices like the iPhone 3GS will encrypt, but it’s still not a great idea.
3. Creating a special policy for “old” iPhones and applying it selectively is probably more acceptable. Administrators can allow certain users to ignore the device encryption policy but still apply it to all others. This commandlet (from Krypted) will create such a policy:
   New-ActiveSyncMailboxPolicy -Name iPhone -AllowNonProvisionableDevices $true
4. Upgrading to an iPhone 3GS is probably the best answer. IT doesn’t need to get involved (as long as you know how to configure Exchange ActiveSync) and no security policies need to be weakened to make it work.

© sfoskett for Stephen Foskett, Pack Rat, 2009. | How iPhone OS 3.1 Locked Some Out Of Exchange, And How To Fix It
This post was categorized as Apple. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

For the most up-to-date information, see my iPhone Exchange ActiveSync Guide!

This post is part of my series focused on integrating the iPhone with Microsoft Exchange using ActiveSync:

• iPhone OS 3.0 information:
  1. First Look: iPhone 3.0 And Exchange ActiveSync Integration
  2. How To Subscribe To Internet Calendars In iPhone OS 3.0
  3. How To Access LDAP Directories In iPhone OS 3.0
  4. iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
• How To Set Up iPhone Exchange ActiveSync
1. A Few iPhone Exchange ActiveSync Gotchas
2. Can the iPhone Sync With Multiple Exchange Servers?

Note that if you are using Exchange ActiveSync for your corporate email, the iPhone will probably already be able to search the Global Address List (GAL) without setting up LDAP. This didn’t work for me under 2.0, but now that I’m using 3.0 I can search the GAL through ActiveSync. Even if you can do this already, there may be other LDAP servers you need to access. Here’s how!

How To Set Up LDAP Access

iPhone 3.0 includes direct over-the-air use of CalDAV, ICS, and LDAP servers

Setting up LDAP is simple. Follow these steps:

1. On the iPhone, select “Settings”
2. Select “Mail, Contacts, Calendars”
3. Select”Add Account…” under “Accounts”
4. Select “Other” at the bottom
5. Select “Add LDAP Account”
6. Enter your LDAP Server’s name (e.f. “ldap.example.com”)
7. You will probably have to enter a user name (e.g. “sfoskett”) for “User Name” and a password for “Password”
8. Optionally modify the description
9. Select “Next” and you’re done!

Your LDAP server should now show up in the Contacts application. You can search and use addresses directly from here, but you can’t edit them or add them to the phone’s address book. LDAP addresses are also integrated into the mail, phone, and SMS apps – just start typing a name and the iPhone will query LDAP as well as any local or synced contacts!

If you have a large LDAP server, you may also have to enter a “search base” to limit the scope of your search queries. You can do this only after you have set up the LDAP account.

1. Go back to “Settings”
2. Select “Mail, Contacts, Calendars”
3. Select the LDAP account
4. Select “Add Search Settings…”
5. Enter your search base string under “Base” (e.g. “ou=people,dc=example,dc=com”)
6. Optionally enter a description
7. Select “Base”, “One Level”, or “Subtree” depending on where you want to search
8. The iPhone tries to use SSL by default. If your server doesn’t support this, it will time out and try to connect without.

You can set multiple Search Settings to allow searches in different search bases from the same LDAP server.

There are some limitations to the iPhone’s LDAP implementation, however:

1. You have to enter the search base manually rather than having it automatically filled in by the software. Cut and paste is very helpful here!
2. It doesn’t appear to support Kerberos authentication
3. You can’t browse the directory (it’s search-only) so you have to know who you’re looking for ahead of time
4. LDAP information is limited to phone numbers, a single work addresses, and a single email address

There you have it! Is anyone aware of a useful public LDAP server? I can imagine all sorts of info that would be nice to have while on the go – airline phone numbers, taxi companies, etc.

© sfoskett for Stephen Foskett, Pack Rat, 2009. | How To Access LDAP Directories In iPhone OS 3.0
This post was categorized as Apple, Personal. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

Check it out! How To Keep Your Family Activities In Sync With A Shared Google Calendar

For the most up-to-date information, see my iPhone Exchange ActiveSync Guide!

This post is part of my series focused on integrating the iPhone with Microsoft Exchange using ActiveSync:

• iPhone OS 3.0 information:
  1. First Look: iPhone 3.0 And Exchange ActiveSync Integration
  2. How To Subscribe To Internet Calendars In iPhone OS 3.0
  3. How To Access LDAP Directories In iPhone OS 3.0
  4. iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
• How To Set Up iPhone Exchange ActiveSync
1. A Few iPhone Exchange ActiveSync Gotchas
2. Can the iPhone Sync With Multiple Exchange Servers?

This is really a major advancement for the iPhone platform. With 3.0, you have many different calendar synchronization options and can mix and match, using all or none as you see fit:

How to Subscribe to a CalDAV Server (Like Google Calendar)

CalDAV is a powerful open protocol for calendar event synchronization. Lots of services support it, including Google’s free Calendar application, which is part of gmail and Google Apps. It’s a mash-up of WebDAV and ICS and supports two-way synchronization, notes, alerts, and such. iPhone OS 3.0 includes CalDAV as a supported protocol for over-the-air subscription and synchronization, so it can seamlessly synchronize your Google calendar with your phone calendar. Unlike ICS, however, you can create and edit CalDAV entries on the phone and the changes will quickly show up in your Google calendar.

iPhone 3.0 includes direct over-the-air use of CalDAV, ICS, and LDAP servers

Setting up CalDAV, though hidden, is pretty slick. Follow these steps:

1. On the iPhone, select “Settings”
2. Select “Mail, Contacts, Calendars”
3. Select”Add Account…” under “Accounts”
4. Select “Other” at the bottom
5. Select “Add CalDAV Account”
6. Enter “www.google.com” for “Server” – the iPhone will automatically identify this as a google CalDAV server!
7. Enter your gmail user name (e.g. “sfoskett”) or full google apps username and domain (e.g. “stephen@fosketts.net”) for “User”
8. Enter your password for “Password”
9. Optionally modify the description
10. Select “Next” and you’re done!

The iPhone recognizes Google Calendar – it’s smart enough to “know” that when you enter “www.google.com” as the CalDAV server it needs to correctly format the URL for Google. Other CalDAV server types might need some tweaking, which you can do in the Advanced tab of the CalDAV’s account in Settings.

All CalDAV calendars are bi-directional, meaning you can create or edit entries and they will (eventually) synchronize on both the phone and calendar server. In my tests, items modified on the iPhone showed up almost immediately, while changes made on Google’s calendar server took a few minutes to show up.

Two notes on CalDAV:

1. Although the documentation says it’s read-only, my Google Calendar absolutely, definitely, is read/write: I can create and modify appointments in the Google Calendar on the iPhone and it shows up online.
2. The “Sync events x weeks back” limit in settings does not apply to CalDAV or ICS! Large numbers of events will cause Calendar to be very, very slow. Beware!

Other popular apps also support CalDAV, including Apple Leopard Server’s iCal Server, Yahoo Calendar, and Zimbra.

I use this capability as a shared family activities calendar. What ideas do you have?

How to Subscribe to an iCalendar Server/.ICS feed

iCalendar is an older calendar subscription format, and many servers offer .ICS feeds of calendar entries. I particularly love TripIt‘s free travel itinerary service, which is available as an ICS feed. iPhone OS 3.0 also includes iCal as a supported protocol for over-the-air subscription, so you can view your ICS feeds right in your phone calendar. Note that iCalendar is read-only, like an RSS feed, so you cannot create or edit items on the phone.

Tap a link to a .ics file and the iPhone will ask to subscribe

The simplest way to subscribe to an ICS feed is simply to email the link to yourself. The iPhone interprets any URL ending in “.ics” as a iCalendar feed and asks if you want to subscribe. This ensures that the link is typed correctly.

Note: This no longer works in iOS 4.2! Now you have to add it in Settings. See Apple Breaks ICS Calendar Auto-Subscription In iOS 4.2.

If you need to manually set up an iCalendar feed, it’s very similar to CalDAV. Follow these steps:

1. Locate the calendar feed you want to use and copy it using OS 3.0′s new copy and paste features
   1. If you use TripIt, log into your account in the iPhone Safari browser
   2. Select the “iCal Feed” icon in your main page
   3. In the popup, select “Subscribe to calendar feed”
   4. Tap and hold the resulting URL (which begins with “webcal://”) until the “Copy” box appears
   5. Tap “Copy”
2. Go back to the hope screen and select “Settings”
3. Select “Mail, Contacts, Calendars”
4. Select”Add Account…” under “Accounts”
5. Select “Other” at the bottom
6. Select “Add Subscribed Calendar”
7. Select the “Server” box and tap “Paste”
8. Select “Next”
9. Optionally modify the description

Updates to the iCalendar feed will now show up in your calendar. These are read only, of course, but it’s awfully nice to be able to subscribe to a TripIt or Dopplr feed or the Red Sox schedule on your phone!

One more time: The “Sync events x weeks back” limit in settings does not apply to CalDAV or ICS! Large numbers of events will cause Calendar to be very, very slow. Beware!

© sfoskett for Stephen Foskett, Pack Rat, 2009. | How To Subscribe To Internet Calendars In iPhone OS 3.0
This post was categorized as Apple, Personal. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

This blog post is probably out of date. If you want to set up Exchange ActiveSync, you should instead consult one my guides:
	iPhone Exchange ActiveSync Setup		iPad Exchange ActiveSync Setup
	iPhone ActiveSync Troubleshooting		iPad ActiveSync Troubleshooting

iPhone OS 3.0 is here, offering enhancements for enterprise Exchange ActiveSync

iPhone OS 3.0 was released today, and I’ve had a chance to play with it for a bit now. I am very impressed with the improvements Apple has made, and think that 3.0 will be much more welcome in Microsoft Exchange environments. However, it’s still not quite up to the high standard set by the BlackBerry.

Wondering how to get Exchange working in 3.0? Start here:
How To Set Up iPhone Exchange ActiveSync

For the most up-to-date information, see my iPhone Exchange ActiveSync Guide!

This post is part of my series focused on integrating the iPhone with Microsoft Exchange using ActiveSync:

• iPhone OS 3.0 information:
  1. First Look: iPhone 3.0 And Exchange ActiveSync Integration
  2. How To Subscribe To Internet Calendars In iPhone OS 3.0
  3. How To Access LDAP Directories In iPhone OS 3.0
  4. iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
• How To Set Up iPhone Exchange ActiveSync
1. A Few iPhone Exchange ActiveSync Gotchas
2. Can the iPhone Sync With Multiple Exchange Servers?

Major Changes

Apple made some significant updates to all three of the components touched by ActiveSync: Mail, Calendar, and Contacts.

• The Calendar has been totally re-done, more smoothly supporting multiple calendars, syncing with local calendars and Exchange at the same time, CalDAV and .ICS natively, and allowing on-phone creation of meeting invitations for Exchange users.
• The Contacts application can now sync with local address books and Exchange at the same time.
• Mail is more flexible, with per-folder downloading of Exchange messages.

As I noted last month, however, OS 3.0 is not all roses. In particular, the following issues continue to haunt the phone:

1. The iPhone only supports full ActiveSync with a single Exchange server. Although you are free to establish as many IMAP connections as you like, including connecting to Exchange with IMAP, you cannot use more than one ActiveSync service.
2. Still no notes and tasks sync (with Exchange). Although iPhone OS 3.0 does allow synchronization of notes with Apple Mail for Mac users, it does not support Exchange or Apple’s own MobileMe over-the-air services.
3. No public folder support.
4. ICS and CalDAV seems to be desktop-sync only.
5. Spotlight does not include full-text search of mail messages.
6. Push email remains slow, flaky, and battery-consuming. This is a very tough nut to crack!

Mail

The mail application gets numerous improvements for all mail servers. Notable among these is landscape mode and spotlight search. When it comes to Exchange ActiveSync, the changes are harder to notice. One thing that struck me was the ability to specify which folders to “push” along with the Inbox. Perhaps this was there all along and I missed it, but I never noticed it before.

Note that the Push settings have been moved under “Mail, Contacts, Calendars” in OS 3.0.

Calendar

OS 3.0 is much more sensible in organizing and synchronizing multiple calendar types

Although iPhone OS 2.0 supported multiple calendars, it was very confusing and not at all integrated with Exchange. OS 3.0 has cleaned things up significantly. As illustrated, the iPhone now organizes calendars into categories: Those synced from the Mac or PC and those synced over the air from an Exchange server.

That’s right – the iPhone can now sync calendar entries over both USB and Exchange at the same time! This is super handy, since iTunes supports CalDAV and ICS subscribed calendars through iCal on OS X, and presumably on Windows as well. I’ve written before about TripIt’s solid iPhone app, and this gives another way to view trips. But the iPhone doesn’t seem to support either CalDAV of ICS over the air, which is something of a disappointment. We can’t have everything, can we? Update: I missed it! iPhone OS 3.0 does include over-the-air CalDAV and ICS!

Of course, the new spotlight search supports calendar entries as well, allowing quick access to appointments.

Perhaps the most-anticipated calendar feature for iPhone OS 3.0 is meeting invite support. I can confirm that it is possible to create a meeting, add attendees, and send invites right from the iPhone, and that this works over the air! This is a specific Exchange feature, so of course it only works for the Exchange calendar. But you can easily change an existing non-exchange item to the Exchange calendar and start inviting attendees, even those not using Exchange.

But there are still limitations. You cannot add invitees to someone else’s meeting. You cannot make any changes to an appointment synced from the desktop (CalDAV and ICS included). You cannot forward a meeting request from the calendar app. You cannot see free/busy time when scheduling. It’s not like you have Outlook in your pocket!

One more weird thing I noticed: Nearly every app now has a landscape mode, including mail and contacts, but calendar is locked in portrait only!

Contacts

Like calendars, contacts now supports both iTunes and over-the-air Exchange syncing

The other application to see some updates is Contacts. Like the calendar app, Contacts can now sync to both local desktop and over-the-air Exchange sources at the same time. The iPhone sync combines desktop sources into an “on my iPhone” category and maintains Exchange contacts separately. It also includes access to an Exchange global address list (GAL), and this seems to work much better now than it used to.

Contact management is somewhat limited, however. If you locate a user in the GAL, you can’t add them to your Exchange or iPhone contact list without copy and paste (did I mention that it works?) or finding an email message from them. The phone also has no de-duplication features, so if your desktop contact list is synced with Exchange already you will have a world of duplicate entries.

Summary

All in all, iPhone OS 3.0 is a worthwhile upgrade, especially for business users. Everything seems to work more smoothly and logically than in 2.0, and the added Exchange calendar invite support is great. The complete set of additions, from copy and paste to spotlight search, are excellent as well. But, like the Mac, the iPhone remains just a bit left-of-center in the world of business and Microsoft Exchange. Maybe that’s for the best!

Check out Paul Robichaux’s comments on 3.0′s mail as well!

© sfoskett for Stephen Foskett, Pack Rat, 2009. | First Look: iPhone 3.0 And Exchange ActiveSync Integration
This post was categorized as Apple, Personal. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

iPhone OS 3.0 is coming, offering enhancements for enterprise Exchange ActiveSync

As the release of iPhone OS 3.0 nears, I set out to discover how the new OS changes the iPhone’s ability to synchronize data with Microsoft Exchange servers using ActiveSync. What follows here is my deductions so far, and is of course subject to change when the new OS is released!

For the most up-to-date information, see my iPhone Exchange ActiveSync Guide!

This post is part of my series focused on integrating the iPhone with Microsoft Exchange using ActiveSync:

• iPhone OS 3.0 information:
  1. First Look: iPhone 3.0 And Exchange ActiveSync Integration
  2. How To Subscribe To Internet Calendars In iPhone OS 3.0
  3. How To Access LDAP Directories In iPhone OS 3.0
  4. iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
• How To Set Up iPhone Exchange ActiveSync
1. A Few iPhone Exchange ActiveSync Gotchas
2. Can the iPhone Sync With Multiple Exchange Servers?

New ActiveSync Features

1. iPhone OS 3.0 allows users to create meeting invitations! Finally, right from the phone, you will be able to set up meetings, select invitees, and send invitations. Initial reports are that this functionality is definite and fairly complete.
2. Enhanced mail search includes contacts, messages, and even mail still on the Exchange server! This is a huge and welcome addition. No longer will you be frustrated that the iPhone didn’t download that one important message from last month, and no longer will you have to scroll around trying to locate it! This is integrated into the new Spotlight screen: Flick left from the home screen and you’ll be able to search email, contacts, calendars, and all other phone content! But Spotlight only searches message metadata, not message content.

New Related Features

1. The calendar app supports CalDAV and ICS calendars as well as ActiveSync, making it much easier to use Google, Yahoo, and TripIt calendars. But these probably will not be integrated and synchronized with the ActiveSync calendar, leaving you in multiple-calendar hell.
2. Peer-to-peer contact exchange using BlueTooth seems certain. Since the iPhone gracefully integrates on-phone changes with ActiveSync contacts already, this will be a welcome way to build out one’s Exchange address book.
3. Cut, copy, and paste are definitely in, and will work in the mail, contacts, and calendar apps!
4. The mail app now supports landscape mode, with its larger keyboard.
5. A new API for email within applications would be compatible with Exchange, allowing a new family of corporate apps and possibly mitigating some of the missing features. I can imagine someone developing a far more feature-packed email client which embeds the native email client and extends its support to public folders, for example.
6. iPhones running 3.0 appear to allow automatic on-demand connections to VPNs. Again, not specifically an ActiveSync feature, but this would make the process of accessing a firewalled Exchange server more friendly.
7. OS 3.0 supports LDAP servers. Although this is not an ActiveSync issue per se, it could allow a workaround for the single-ActiveSync issue (which remains). LDAP contacts would make the basic IMAP email connection with a second Exchange server somewhat more tolerable. But it’s not yet clear if LDAP contacts are all that functional in 3.0, or whether they’ll make the cut at all.

Bad News

1. The iPhone will remain limited to full ActiveSync with a single Exchange server. Although you are free to establish as many IMAP connections as you like, including connecting to Exchange with IMAP, you cannot use more than one ActiveSync service. However, as noted above, 3.0 does include LDAP support so at least the contacts from your second Exchange server might be accessible.
2. Still no notes sync (with Exchange). Although iPhone OS 3.0 does allow synchronization of notes with Apple Mail for Mac users, it does not appear to support Exchange or Apple’s own MobileMe over-the-air services.
3. Spotlight does not include full-text search of mail messages. Although it’s nice to be able to search through everything on the iPhone, and even content on the Exchange server, you still have to remember the sender, subject, etc.
4. Battery life is poor with Exchange ActiveSync push and the new push notifications enabled. iPhone push battery life has been a problem for quite a while.

As the iPhone OS 3.0 release nears, I will keep my eyes open for enterprise Exchange ActiveSync features and post them here. Subscribe to my Apple feed for up-to-date details!

© sfoskett for Stephen Foskett, Pack Rat, 2009. | iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
This post was categorized as Apple. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

The iPhone doesn't support more than one Exchange/ActiveSync pairing

One of the major advances introduced in iPhone software version 2.0 was the ability to sync over-the-air to Microsoft Exchange servers using Microsoft’s ActiveSync protocol. This was introduced to much fanfare with the iPhone 3G and is available on older updated iPhone and iPod Touch units, too. Google and NuevaSync also offer over-the-air calendar and contact syncing for the iPhone using ActiveSync.

All of these synchronization options seem like an embarrassment of riches for iPhone users. But, like so many things in life, they’re too good to be true. iPhone OS 2 and 3 can’t sync to more than one Exchange/ActiveSync server at a time! Or, at least, not in the way you’d like.

Note: iPhone OS 4.0 will allow syncing to multiple Exchange ActiveSync accounts! See How To Set Up Multiple Exchange ActiveSync Accounts in iPhone iOS 4.

For the most up-to-date information, see my iPhone Exchange ActiveSync Guide!

This post is part of my series focused on integrating the iPhone with Microsoft Exchange using ActiveSync:

• iPhone OS 3.0 information:
  1. First Look: iPhone 3.0 And Exchange ActiveSync Integration
  2. How To Subscribe To Internet Calendars In iPhone OS 3.0
  3. How To Access LDAP Directories In iPhone OS 3.0
  4. iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
• How To Set Up iPhone Exchange ActiveSync
1. A Few iPhone Exchange ActiveSync Gotchas
2. Can the iPhone Sync With Multiple Exchange Servers?

The Connected iPhone

Let’s back up a minute and talk about how the iPhone integrates with mail, contact, and calendar servers. There are essentially two synchronization engines at work here:

• Like all iPods, iTunes can synchronize your contacts, calendars, and mail account information (though not the mail messages themselves) over a USB connection to the iPhone and iPod Touch. This requires a full copy of Outlook 2003 or later on Windows but works with the built-in address book and iCal calendar on Mac OS X.
• The iPhone can also synchronize some or all components of email, contacts, calendars, and bookmarks using a variety of over-the-air protocols.

Note that when you configure over-the-air sync, you must disable USB sync, and vice versa.

iPhone Email Sync

Configured mail accounts can synchronize email messages in one of six ways:

1. Periodically pulling message content down using the POP protocol – this is what most older ISPs and mail accounts use
2. Periodically pulling message content down using the more advanced IMAP protocol – this is what newer mail accounts, including Gmail, AOL, and Yahoo use
3. Having mail pushed to the phone using a weird combination of hidden SMS and IMAP – this is what Yahoo push mail uses
4. Having mail pushed to the phone using a proprietary notification system of XMPP (Jabber) and IMAP – this is what Apple’s MobileMe push mail uses
5. Pulling or receiving push messages using Microsoft’s ActiveSync technology – this is what Exchange servers, NuevaSync, Kerio, Zimbra, and Google’s over-the-air calendar and contact (but not email) sync use
6. The iPhone’s software seems to support IMAP Idle, which is a realtime message push technology supported by Gmail and some advanced mail systems, but the phone will not use it unless the mail application is actually open on the phone

The iPhone does not support P-IMAP, BlackBerry, or other over-the-air protocols at this point.

The iPhone can sync email messages to any number of IMAP or POP accounts without a problem, but it can only sync to a single ActiveSync server at once. So you can set up Gmail over IMAP, Yahoo over SMS/IMAP, your local provider over POP, a Gmail Apps account over IMAP, etc at the same time as your work Exchange server without a problem. But you cannot set up more than one Exchange server using ActiveSync.

iPhone Calendar and Contact Sync

Calendar and contact information can only be synced in one of (perhaps) three ways:

1. Over a physical USB connection to iTunes (as in the original iPhone 1.0) to Outlook or OS X
2. Using some unknown protocol that MobileMe uses – can anyone identify this?
3. Using ActiveSync to an Exchange Outlook Web Access (OWA) server

Yes, that’s really it. Every over-the-air calendar-and-contact sync system (other than perhaps MobileMe) uses the ActiveSync protocol, including Microsoft Exchange, NuevaSync, Zimbra, and Google’s service.

Now the punch line: The iPhone can only sync to a single ActiveSync server at once. Read that again. Now consider what that means.

So no matter how cool a service is (Google sync, Zimbra), you cannot use it for over-the-air sync if you are also connected to an Exchange server. So even though the iPhone explicitly supports multiple calendars, you can’t sync them with multiple ActiveSync systems. So I guess the iPhone’s calendar system is even more disappointing than I thought!

Pick One ActiveSync Service

The upshot is this: iPhone users much pick one (and only one) ActiveSync service.

• Need to use the iPhone for work? You’ll probably have to use your work Exchange ActiveSync server, and can forget about (usefully) subscribing to MobileMe or using Google sync. Instead, try to sync everything else into Exchange in other ways (like Google’s Desktop app) and then let Exchange handle the iPhone sync.
• A dedicated Mac head? Subscribe to MobileMe and get all of your data there, to be sent to the iPhone.
• None of the above? Google’s new Sync service looks great!

The Big Mystery

There are many mysteries lurking here, but one is really perplexing to me. The iPhone seems to maintain its own set of contacts in addition to any ActiveSync contact store. Although it doesn’t obviously have multiple contacts pools, it must maintain them internally. But you can see that it does in a simple way:

1. Set up an ActiveSync server (like Exchange)
2. Set up an IMAP email account (like Gmail)
3. Add a unique contact on the phone (call him “Steve Jobs”)
4. Add a unique contact in Exchange (call him “Bill Gates”)
5. Add a unique contact in Gmail (call him “Sergey Brin”)
6. Now turn on and off the accounts one at a time

Notice that turning off the Gmail account will, within a few minutes, cause your “Sergey Brin” contact to disappear! Turn it back on and Sergie is back. Now do the same for Exchange and Bill Gates. All the while, your “Steve Jobs” contact should stay put. And this all happens in a single contact list! If you assigned one of these to a “favorite”, their name will be replaced by their number when you remove their account.

So the is iPhone somehow syncing contacts over IMAP? Or does it use some other Google-specific protocol? And how does MobileMe’s contact sync work? Time will tell!

© sfoskett for Stephen Foskett, Pack Rat, 2009. | Can the iPhone Sync With Multiple Exchange Servers?
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For the most up-to-date information, see my iPhone Exchange ActiveSync Guide!

This post is part of my series focused on integrating the iPhone with Microsoft Exchange using ActiveSync:

• iPhone OS 3.0 information:
  1. First Look: iPhone 3.0 And Exchange ActiveSync Integration
  2. How To Subscribe To Internet Calendars In iPhone OS 3.0
  3. How To Access LDAP Directories In iPhone OS 3.0
  4. iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
• How To Set Up iPhone Exchange ActiveSync
1. A Few iPhone Exchange ActiveSync Gotchas
2. Can the iPhone Sync With Multiple Exchange Servers?

I’m a long-time iPhone user and new Mac switcher, but since I use the phone for business (read Exchange) email, contacts, and calendars, I was stuck syncing it to the (work) PC instead of the (home) Mac.  This really wasn’t optimal, as it meant I needed to load all of my songs and movies on the work machine, which is a serious no-no for my “keep ‘em separated” computing preferences. But the iPhone has to be synced to a single machine, and since I needed to be able to keep my contacts and calendars up to date, I was stuck.

All this changed with 2.0′s over-the-air sync ability, though. Once you enable Exchange ActiveSync (or MobileMe, for that matter), you no longer have to tie the iPhone to Outlook. So now I am able to sync my work contacts, email, and calendar to Exchange and my songs, ringtones, apps, and movies to my Mac! Joy!

I first noticed this shortly after my 2.0 upgrade and ActiveSync activation. I docked the iPhone to the Mac to download some photos with iPhoto, and I noticed that iTunes would let me “sync” it there, even though it was “paired” to the PC. Although I had selected “manually manage music”, I couldn’t drag and drop songs or videos, but I noticed that the calendar, contacts, and mail sync settings were now grayed out. This got me thinking, so I decided to take the plunge and blow away all of my content in order to really sync the phone to the Mac. Sure enough, my mail, contacts, and calendars remain connected to Exchange, but everything else now lives on the Mac.

I wonder if Apple considered this implication when they released Exchange ActiveSync. After all, it would seem to tie the phone more strongly to Microsoft but actually has the exact opposite effect. I don’t need a Windows PC at all anymore!

© sfoskett for Stephen Foskett, Pack Rat, 2008. | iPhone and Exchange: Push Email? Great! Switch to Mac? Priceless!
This post was categorized as Apple, Personal. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

One of the most common questions I’ve been hearing after I published my articles on how to set up Exchange ActiveSync with the iPhone 2.0 software is whether or not you need an enterprise data plan from AT&T in order to use it.  There were conflicting rumors going around prior to the launch, and AT&T and Apple haven’t been clear on the subject.

Here’s the answer:  You do not need to buy the $45 Enterprise Data plan from AT&T for Exchange ActiveSync and corporate VPN access to function with an iPhone 3G or upgraded original iPhone.

This may not be the whole story, though.  Although the Exchange and VPN features exist and are functional with either the $20 EDGE or $30 3G data plans from AT&T, the company may require you to buy the $45 Enterprise Data plan.  I am not a lawyer, but the terms and conditions are no help.

And the wording on the iPhone web site and iPhone business site aren’t clear, either:  They say you must get the Enterprise Data Plan “to access corporate email, company intranet sites, and/or other business solutions/applications”.  Although this would certainly include business Exchange users, it would also include non-Exchange users accessing business sites, as well as business users accessing their Exchange server with IMAP.  And it would seem to exclude those using Exchange for personal email (which is quite possible).

Note that, although these enterprise features are fully functional in EDGE iPhones with 2.0, there is no Enterprise Data plan for them!  So if you have an original iPhone you have to use the $20 data plan no matter what!

Finally, although I can’t tell you whether AT&T allows it explicitly, many people have been successfully using their iPhones to access Exchange ActiveSync with both the $20 and $30 data plans with no problems at all.

© sfoskett for Stephen Foskett, Pack Rat, 2008. | Yes, Exchange ActiveSync for iPhone Works Without a Business Data Plan
This post was categorized as Everything. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.