How To Move Your Contacts, Calendar, Email, Bookmarks, and Photos to the iPhone

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More and more people are switching to the iPhone. They’re switching from Palm and Windows Mobile and Blackberry smartphones to the iPhone. They’re switching carriers to get the iPhone. And now that the next-gen iPhone 3G is all but upon us, and more and more regions are announcing their plans and pricing, the switching is only going to get faster and more furious.

To celebrate the switchers, those who dare to phone different, the iPhone Blog wants to help you get your content off your old, perhaps restrictive and outdates systems, and onto your shiny, new iPhone.

We’ve already gone over how to move your music, movies, and other media to iTunes, so now it’s time to get with the data: contacts, calendars, and email.

Read on to find out how!

This article assumes you’re switching from another smartphone, like Blackberry, Windows Mobile, or Palm, and are new to the iTunes + iPod (and iPhone!) ecosystem. It also assumes you’re a dedicated Windows user or someone who just recently switched from Windows to the Mac and needs to transfer content to an iPhone.

Since longtime iPod (and Mac) aficionados will almost certainly already be using iTunes and the typical Mac applications, your iPhone will sync your content via iTunes the same as it would any other iPod. And, hey, if you’re a Linux (or any other *nix) user, I figure you’ve kept your content open from the get-go, and already know 18 different ways to get it onto your unlocked, jailbroken iPhone hax0red with Open Moko anyway…

“Push” First: Microsoft Exchange ActiveSync and Apple MobileMe

While with previous iPhone firmware, there was tethered (via iTunes) sync between Outlook and the iPhone, and between the default Apple apps and the iPhone, it was on a type-by-type basis (see screenshots in the iTunes section), and only when you actually hooked up your iPhone and pulled down the data would both your mobile and local copies get synchronized.

With iPhone firmware 2.0, everything changes. Why lead with this? Because if you intend to use either Exchange and/or MobileMe with your iPhone, you can read this section and you’re pretty much done. (Or at least you can skip ahead to photos at the end — though be sure to download iTunes anyway for your media). With Exchange and MobileMe (billed as Exchange for the rest of us), iTunes data sync is eliminated, cables are eliminated, and intermittent syncing becomes a thing of the past. With these “push” solutions, everything is automagically updated wirelessly (via WiFi or EDGE/HSPA cell network). Change something in Outlook and a few seconds later, your iPhone will show the same changes. Tweak some data on your iPhone, and a few seconds later, MobileMe’s website will show the same tweak.

(Not using ActiveSync or MobileMe? No worries. Skip to the next section and we’ll start setting up iTunes for local sync!)

So, to simply and easily set up most of your syncing using iPhone 2.0: tap Settings, tap Mail, Contacts, and Calendars (Just Mail if you’re doing Exchange on iPhone 1.x), tap Add Account, and then select the type of account you would like to add.

Microsoft Exchange ActiveSync

ActiveSync makes its debut with iPhone 2.0, and doesn’t function on the older, 1.x firmware, so if you intend to use it, make sure you have an iPhone 3G or have updated your original iPhone (2G) to the latest firmware as of July 11, 2008. To setup Exchange ActiveSync, tape the logo for it. If you’re using Exchange 2007 on the back end, you may be able to automatically set up your account. If you can’t, or are using an old version of Exchange — or just in general due to the complex and fussy nature of setting up an Exchange account in general — you’re best practice is to check with your Exchange administrator (or hosted service provider).

Apple MobileMe (formerly .Mac)

MobileMe, Apple’s replacement for .Mac and it’s “Exchange for the Rest of Us”. It will sync, wirelessly, over the air (OTA), contacts, calendars, mail, and photos between the iPhone and your Mac (with the aforementioned Address Book, iCal,, and iPhoto) and/or PC (with Outlook). MobileMe will debut on July 11, 2008 alongside iPhone 3G and the 2.0 firmware, and should “just work” once you enter in your MobileMe username and password (previous users of .Mac will keep the same credentials, and will be able to use either or interchangeably).

Local Sync: Getting iTunes

iTunes is a free download from and required before you can sync your iPhone. The iPhone 3G will require iTunes 7.7, which will be released day-and-date with the next generation device, so if you’re reading this before July 11, 2008, you’ll need to wait a bit before downloading, or will need to upgrade to that version.

What Data Does iTunes Sync?

Aside from the media we covered in the previous article, Apple’s iPhone 3G will sync the usual data suspects of address book contacts, calendar events, email accounts, web browser bookmarks, and — because we didn’t include them under media — digital photographs.

If you already have your data in Outlook, you’re good to go for the iPhone. If you have it in another application, or scattered among a few applications… well, we’ll get to that in a moment.

On the Mac side, iTunes “just works” with Apple’s default applications, Address Book, iCal,, Safari, and iPhoto, or with Microsoft’s Entourage. Since sync services, contacts, calendaring, etc. are all “CoreServices” handled at the OS level, once you check the appropriate boxes in iTunes, the automagic process is almost transparent. You can even sync to Microsoft Office Entourage (Outlook’s ugly step-sibling on the Mac side) by syncing Entourage with the default apps via CoreServices.

Similarly, if you don’t have your data in these Mac apps yet, or have it scattered elsewhere, we’ll also get to that in a moment.

Now let’s break it down…

Syncing Your Contacts

From Microsoft Windows Vista & XP: Outlook, Windows Contacts, and Yahoo! Address Book

These three protocols are all supported from directly within iTunes. If you have your contacts in one of them, simply choose the appropriate program from the drop-down in iTunes and your information will be moved right over to your iPhone.

From Apple OS X: Address Book, Yahoo! Address Book, and Google Contacts

On the Mac version of iTunes, you can check both Apple’s Address Book and Yahoo! Address Book if you so choose. (I keep things simple — and fear duplicates — so I recommend picking one and sticking with it.)

If you’re running OS X Leopard 10.5.3 or later, you can also sync your Gmail Contacts with your iPhone, using a more round-about method: launch Address Book, select Preferences from the Address Book menu, and check the box next to Synchronize with Google. Once set up, this will sync your Google Contacts to your Address Book, and then iTunes will sync them from Address Book to your iPhone.

From Everywhere Else: Thunderbird, Windows Live, Google Contacts

If you have your contacts in anything other than the above-mentioned programs or services, you’ll have to move them over before you can sync them with the iPhone. Many programs/services allow you to export CSV files or vCards, including: Mozilla Thunderbird, Microsoft Windows Live, and Google Contacts.

Once you’ve got your export file, simply import the contacts back into Outlook, Address Book, Yahoo! Address Book and you’re golden.

Syncing Your Calendar

From Microsoft Windows Vista & XP: Outlook

For reasons known only to Apple and Microsoft, Outlook is your only calendar/event choice for syncing with the iPhone. (The drop down is so far only a merciless tease at options yet (maybe never?) to come).

From Apple OS X: iCal

Like Windows, OS X provides only one option for calendar sync: iCal (and not even a drop down to tease more.) Check it and go.

From Everywhere Else: Google Calendar, Windows Calendar, etc.

Many popular Calendar programs are compatible with the iCalendar format, which allows you to publish and/or subscribe from one program (and even platform) to another. Using this feature, you can try to move your data over your iPhone. Here’s an example using Google Calendar:

You can subscribe to Google Calendars through Outlook on Windows, or use the Google Calendar Sync utility. Unfortunately the iPhone thus far doesn’t reliably sync from anything besides the Outlook default Calendar, which means the subscribed Google Calendar doesn’t get moved over unless you use a commercial product like the Paul Thurrott referenced SyncMyCal.

For Mac users a one way (Google to iPhone) work-around involves subscribing to your Google Calendar. From Google Calendar: Click on the Calendar Settings drop down, click on Private Address, and click on iCal to generate a private address for your Google Calendar especially designed for iCal. Copy the URL and open iCal. Inside iCal: Select the Calendar menu and click on Subscribe, then paste in the Private Address you copied from Google Calendar. Next time you sync, iCal will feed your Google Calendar to your iPhone. For bi-directional sync (Google to iPhone and iPhone to Google), there’s the commercial Spanning Sync, and you can try the demo before you buy.

Theoretically, you could also try exporting and importing XML, CSV, or another cross-program file, although in my experience this often requires a vast amount of work (and Googling, and message board begging…)

Syncing Your Email

From Microsoft Windows Vista & XP: Outlook and Windows Mail

Two options for Windows users, the ubiquitous Outlook and Windows Mail (which I believe is an “upgrade” to the horrible Outlook Express rather a desktop version of the far superior WIndows Live Mail — tsk tsk to both Apple and Microsoft).

From Apple OS X:

Still only one choice from Apple OS X users, however: Apple’s default mail client, the eponymous Again, just one checkbox, to keep with the ultra simple groove. (Usability over options is a mantra).

From Everywhere Else: Google Gmail, Yahoo! Mail, AOL, Microsoft Live/Hotmail, etc.

Yahoo! Mail can be setup as an IMAP email account on your iPhone, which means your Yahoo! Mail folders on your iPhone will exactly match your folders on Yahoo!’s website and vice versa. Also, Yahoo! provides “push” email for the iPhone, meaning changes to one will be reflected automatically and near-instantly in the other, just like Exchange ActiveSync and MobileMe (but without the calendar and contacts sync).

You can also set up your Gmail account, including the new Gmail IMAP service which works like Yahoo! Mail — but without the “push” — keeping your web, local client (i.e. Outlook, Mail, etc.), and web-based views synchronized at user-definable intervals (manually, every 10 minutes, etc.).

Unfortunately, since they don’t (to the best of my knowledge) surface any open, standard protocols like IMAP or POP, Microsoft Live/Hotmail accounts can’t easily be synced with the iPhone. Your options include signing up for a Yahoo! or Gmail account and manually moving the messages over to your new, IMAP-happy account, or you can try this free solution and see if it works for you.

For any ISP mail, you can simply set up the iPhone as a POP (or IMAP if they offer it — much better!) client.

Syncing Your Bookmarks

From Microsoft Windows Vista & XP: Internet Explorer and Safari

iTunes supports syncing over all your bookmarks from Internet Explorer (hopefully the much more secure and standards friendly IE 7, right?) and Windows Safari (Apple’s own browser). Hierarchies will be preserved, so think about how you’ll use your booksmarks both on the desktop and the iPhone, and organize a good middle ground.

From Apple Mac OS X: Safari

No choices here. Check Safari and move along.

From Everywhere Else: Firefox, Opera, etc.

If you’re using Firefox, Opera, or another Firefox-like (Mozilla Gecko powered), or Safari-like (Apple WebKit powered) browser, is to try and import your bookmarks into Internet Explorer or Safari (export first via HTML if you have to).

If you want to keep using Firefox (or another browser) for desktop use, there’s no way to keep your bookmarks synced, unfortunately, but you can delete the IE or Safari bookmarks (since you’re not using them) and re-import a fresh, updated set whenever you like.

Syncing Your Photos

From Windows Vista & XP: Folder Sync

For Windows users, the procedure to sync photos to the iPhone is as simple as it is non-powerful. Put all the photos you want to sync in a folder (or hierarchy of folders if you want to separate them out, e.g., Family, Friends, Birthday, etc.) and then select that folder in iTunes.

From Apple Mac OS X: iPhoto and Folder Sync

For Mac users, in addition to the folder sync described above, you can also chose to sync from Apple’s iPhoto application, either your complete library, or from selected sub-libraries.

From Everywhere Else: Yahoo! Flickr, Facebook, Google Picasa, etc.

If you keep your photo collection online (i.e. Flickr, Facebook, Photoshop Express, Windows Live, etc.), you’re going to have to target a desktop backup, or download the photos you want on your iPhone to a local directory. Put all the photos you want to sync in one folder, and make sure you note down the location of that folder (e.g. iPhone Photos). This will be the folder you target inside iTunes as described above.

For Picasa, make sure you organize all the pictures you want on your iPhone into one folder, or a hierachy of folders, and then that will be the folder your target from inside iTunes, also as described above.

Wait! Help! My Data is Stuck On My Phone!

On the off chance that some of you don’t use a desktop, laptop, web service, or anything besides your mobile (smart)phone for your data, here’s a down and dirty guide to help you get started.

From the Original iPhone (iPhone 2G) to iPhone 3G

Apple provides excellent directions for upgrading to the iPhone 3G.

From RIM Blackberry, Windows Mobile, and Palm Treo (Windows Mobile OS)

Blackberry’s are data monsters. Data — all of it, all now, all the time — is the only reason for a Blackberry. It’s why RIM invented the Blackberry. Windows Mobile, whether running on a Motorola, Samsung, HTC, Palm, or whatever device, is made to integrate with other Microsoft products like Exchange, ActiveSync, and Outlook/Entourage. (Note: Always make sure you have the latest/greatest firmware, patches, updates, etc. from your phone carrier and platform provider).

From a Blackberry or ActiveSync perspective, pretty much all business users will have an Exchange server of one kind or another available to them. Just use ActiveSync on your new iPhone 2.0 and you’re good to go. (Check with IT if you have to, especially for the settings information).

If you don’t have a business Exchange server but you do have access to a Windows computer with Microsoft Outlook on it, sync your Blackberry to Outlook, then Outlook to your iPhone.

For Mac users, check out Markspace, which provides a variety of phone-specific syncing solutions especially for the Mac. They’re not free, but the time and effort they’ll save you are well worth it. (I used to it get my data off a Palm OS Treo 680 into the default Apple apps and it worked seamlessly).

If you don’ have any of the above available to you, try a hosted Exchange service, even temporarily. Sync your Blackberry data to that, then ActiveSync it to your new iPhone, and cancel the hosted Exchange service.

From Palm OS Treo

Palm OS (Garnet) Treo’s can work similarly to the above if you have ActiveSync installed (or download it from Palm’s website – warning, direct file link!) and access to an Exchange server (business or hosted).

Similarly if you have access to Outlook. If you’re stuck in Palm Desktop, you’ll first have to find your Palm install CD and go through the setup again, choosing Outlook instead.

(Mac users, see Markspace, above).

From a Feature Phone

If you don’t have a smartphone, but are coming instead from a standard consumer feature phone (candybar or flip phone from Nokia, Motorola, Samsung, etc.) and have data on there you really don’t want to retype, you can try looking for a data transfer kit that matches your phone. These vary widely in form, availability, and functionality, and will cost you money and time, but if you have both check out Howard Forums or even Google. Search and ask around. Be key word specific (i.e. “transfer data nokia model# outlook”. Best of luck, and please share what you find in case others are trying out the same.


Well, there they are, my tips and tricks for getting your data off the old and outdated just in time for your brand new iPhone 3G/2.0. But try as I might, I know our readers — the real data ninjas — have a whole host of sneaky black magic all their own.

What are your best tips and tricks? Drop a comment and let us know!

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About author

Jarrett Gucci
Jarrett Gucci 289 posts

Jarrett Gucci is the owner of Dynasty Web Solutions. A full service Internet presence provider specializing in WordPress development for business owners. Jarrett Gucci along with his team of professionals have designed over 400 WordPress websites. Jarrett Gucci believes strongly in creating websites that are unique, functional and generate referrals.

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