Published on MacDevCenter (
 See this if you're having trouble printing code examples

Making a Smooth Move from .Mac to Google

by Matthew Russell

Apple's .Mac product is a topic of much contention these days. For roughly $100 per year, some members feel like they're getting a good deal while others periodically wonder why they're paying money for stuff that they can get gratis via Google. Chuck Toporek's The .Mac Tax blog post is a bit dated, but still provides a relevant summary of the highlights from various points of view. Two issues near and dear to my own heart are .Mac's unwillingness to provide server-side spam filtering and the ability to edit calendars on the Web.

This article doesn't even attempt to try and make the hard decision of whether or not you should allow your .Mac account to expire. Actually, this article assumes you've already made that choice and presents a practical approach you can follow to get yourself on track for a smooth move to a Google-centric web experience. Getting your mail, address book, calendar, online storage, online photos, and blog squared away are among the topics we'll investigate.

First Things First: Setting Up GMail

Email is a good starting point, so let's dive right into this one first. Google's mail service is called GMail and provides a nice Web 2.0 experience. It's well integrated with Google Calendar and Google Talk, provides a novel approach to consolidating discussion threads, and gives you powerful searching abilities to find anything in your account. In fact, Google's advice is "never delete anything." Instead, just search for it.

Get an Invite

You can't just go to and sign yourself up like other mail services. Instead, you must have someone with an existing GMail account send you an invitation, or sign up through your mobile phone. Google's Help Center addresses this topic by stating that the referral system is in place to prevent abuse. Whatever the case, you probably won't find getting an invite very difficult since you're bound to know at least one person with a GMail account already. You might also try checking on the Gmail Tools site, where folks often publicly share invites.

Forwarding Mail from .Mac to GMail

Once you have received a GMail invite and have set up your account, you'll probably want to have your .Mac mail forwarded to your new GMail account. In fact, one of the nice features of GMail is that you can have multiple accounts forward to it and still reply from each of those accounts within GMail itself. To get all of your .Mac mail forwarded to your GMail account, just login to .Mac via the Web and choose to forward your mail to your new GMail account. It's probably a good idea to leave a copy of the forwarded messages on the .Mac server (at least for a while), just in case you change your mind.

Thumbnail, click for full-size image. Thumbnail, click for full-size image.
Configuring .Mac settings to start forwarding messages makes switching to GMail easier. Google allows you to use other accounts from within GMail itself.

Forwarding your .Mac mail takes care of new mail that comes your way, but you probably want all of your existing mail sent over to GMail too, right? There are a variety of ways to accomplish this, but the simplest one seems to be creating a new rule in Mail to redirect all existing messages to your GMail account. To create a new rule in Mail, simply go to the Rules tab in Preferences and use the rule builder. Depending on the size of your inbox, you may want to just minimize Mail and come back to it in awhile. Google offers its own tips for switching on its GMail Help Page

Apple Mail Redirect Rule
Setting up a rule in Mail to redirect existing email to GMail.

Importing Your Address Book and More

You certainly don't want to be without your Address Book when you're working in GMail, and fortunately, all it takes is a simple run of the Address Book to CSV Exporter script to get your contacts in GMail, where they'll be intelligently presented in Google Suggest style as you type in recipients to messages you compose or forward.

You might choose to use Apple's Mail application with your GMail account. It's easy; just set up Mail accordingly. Of course, if you really like Mail's interface, make sure to explicitly factor that into your calculus to drop .Mac since the .Mac team just recently unveiled its new webmail interface that looks remarkably similar to Mail (although there's still no server-side spam filtering.)

If you're not sticking with Mail, you might recall that a handy feature Mail offers is auto-completion while you're typing in recipients to messages--even recipients that aren't in your Address Book. On many occasions, this feature may have saved you when you couldn't remember someone's email address, had no record of messages from them, and didn't know where else to look. As of Tiger, Mail keeps track of all recipients from message traffic and makes them available via auto-complete by stashing this information in ~/Library/Mail/Envelope Index, which is an SQLite cache file.

It may not be obvious how to extract the information from an SQLite file, but there's really not much to it. You can simply point the SQLite Database Browser at Envelope Index and then browse the "addresses" table, or you can run this Python script to produce a CSV file of email addresses and names from Envelope Index. (Note that you will need to install pysqlite to run the script.) Once you've used the script to export the file, consider emailing yourself a copy, so you'll never be in a hard spot because you forgot to put something in your address book. Or just sit there and marvel for a while at how many different addresses are in it.

SQLite Browser
Use the SQLite Database Browser to inspect your Envelope Index file, which contains email addresses that may be useful.

Finishing Touches

A couple of finishing touches to consider with GMail include setting up a signature to let people know that you're migrating away from your .Mac account, and adding a thumbnail image of yourself, which GMail and GMail's built-in version of Google Talk share with others much like Mail and iChat do. Your signature might say something to the effect of "I'm switching to GMail and won't be checking anymore after 1 Jan 07. My new address is Please update your address books."

Get Your Calendar In Order

Accessing your calendar is our next stopping point for a smooth move away from .Mac. Fortunately, Google Calendar makes it easy to import all of your existing iCal calendars, which .Mac syncs to the Web for you. From within iCal, simply use the "Export" feature from the "File" menu and then import the calendars via Google Calendar's "Import Calendar" features under "Settings."

GMail didn't require you to officially make any changes you couldn't undo while testing out the waters, and neither does Google Calendar. Its ability to export your calendars allows you to get them back into iCal without missing a beat if you decide Google Calendar isn't going to work out for you.

Google Calendar import screen
Google Calendar makes it easy to import existing calendars from iCal.

Google's designers took no shortcuts when designing its rich web interface. Clicking on the corresponding time block in the calendar presents an intuitive dialog that allows you to quickly add an event by providing only a brief description. You can enter more details by clicking on the "edit event details" link.

Thumbnail, click for full-size image. Adding events in iCal
Google Calendars offers an intuitive interface for quickly adding events much like iCal. In either case, simply clicking in the corresponding spot in your calendar adds a container that you can populate with event information.

Once you've added an event to your calendar, click on it to pop up a dialog that provides a slightly more detailed listing of the event's information. From here, you can also proceed to edit the event's details or delete the event. Deleting the event exposes a really neat feature of Google Calendar--it's modal dialog box, which covers the screen in a translucent layer and forces you to make a decision.

View event information Thumbnail, click for full-size image.
Google Calendar's interface is remarkably rich and Web 2.0-ish; deleting events even produces a modal dialog that freezes everything behind it.

Thumbnail, click for full-size image.
When you edit events, you're able to share the calendar and discuss events in the calendar in addition to the standard editing operations. (Click for full-size image.)

A few other items to note are Google Calendar's "Quick Add" feature, its advanced search capability, and its notifications feature that can send SMS messages to your cell phone. The "Quick Add" feature allows you to type a basic description of an event and have Google Calendar (attempt to) intelligently add it. For example, you might type something like "lunch tomorrow at 8pm with Sally" instead of manually picking the time. In the end, it just saves you a few clicks. The key to not being frustrated with this feature is to choose a simple convention like the example and stick with it.

The advanced search capability is probably overkill most of the time, but it's there if you need it or have an incredibly complex calendar to manage. The ability to have event notifications in your calendar sent to your cell phone is one particularly awesome feature of Google Calendar--if you have a plan that's conducive to receiving SMS messages--and setting it up really is as easy as it looks. Of course, if you spend a lot of time on a computer, having email notifications sent to you can be almost as handy.

Thumbnail, click for full-size image. Thumbnail, click for full-size image.
Google Calendar offers advanced search and a variety of notification options.

Desktop Convenience With Google Notifier

GMail and Google Calendar's rich web features are great when you're in a browser, but sometimes you may not want to go into a browser to check if you have mail or look at your calendar. Google Notifier is a slick, minimally invasive program that runs up in your menu bar and features Growl support for notifications such as receiving new mail. You can easily scan the next few items in your calendar and read the beginning of the top items in your mailbox without ever leaving whatever you're doing on your desktop.

Growl Support Menubar Mail
Google Notifier features Growl support and allows you to preview messages without leaving whatever you're currently working on.

Online Storage

One of .Mac's strong points is its ability to provide you with a convenient online storage solution. Although Google is rumored to soon be providing an official online storage system via a new GDrive service, nothing official is out yet. Nonetheless, some clever folks have figured out ways to hack GMail's file system to provide you with ways of storing information online using GMail. For Mac users, gDisk is a nice frontend for uploading files.

Basically, gDisk and other software like it (GMail Drive for Windows and GMail Filesystem for Linux) use a clever hack that allows you to store information online by creating a special draft message with an attachment that corresponds to the file you uploaded. When you're using the gDisk client, you access the remote file via the gDisk interface and never need to know what's going on in the back room. When you're on the go and don't have ready access to the client software, you can just yank attachments right out of your Drafts folder from within GMail.

If online storage is of particular interest to you, it might also be worth noting that GMail currently offers you almost 3GB available for gDisk-related activities while .Mac storage caps you out at 1GB.

Google Groups

Just as .Mac allows you to create .Mac groups, Google offers you Google Groups. A big benefit of Google Groups over .Mac Groups is that you don't have to be a GMail member to be in a Google Group, whereas you do have to have a .Mac account to create or be in a .Mac group. Creating a group in .Mac also costs you 30MB of storage. Basically, Google Groups are a Google-endorsed way of creating your own custom mailing lists.

Blogging and Photocasting

Apple's fairly new iWeb application explicitly integrates blogging into your .Mac experience, but you could have used an application like iBlog to manage a blog hosted with .Mac for a long time now. Of course, you probably already know that Google has owned Blogger since 2003, so you can get your blog on Google-style as well. Feel free to use your favorite OS X blogging tool to blog to your heart's content with your new Blogger account instead of your .Mac account.

Likewise, you can share photos via Google's recently released Picasa Web Albums tools; there's both a standalone application and a plugin for iPhoto. Although not yet available for OS X, Picasa's integration with Hello for Windows users is every bit as sophisticated as a .Mac photocast, so hopefully it won't be long before a universal binary or web-based application becomes available. Until then, you can still share photos with Picasa in a few other ways, or try out a Flickr feed from Flickr (a Yahoo! company.) Currently, you get 250MB for free with your Picasa account and have to pull out the wallet if you want more space.


Another of .Mac's strong suits is its ability to synchronize your data and settings over multiple machines. An overview of moving to Google wouldn't be complete without addressing this topic, but it turns out that there's not a lot to say. Since Google services are inherently web-based, synchronization takes care of itself. One synchronization tool Google does offer, however, is the Google Browser Sync Firefox extension. It's capable of keeping your browser settings such as bookmarks, history, etc. synced up across multiple browsers and can even restore browsing sessions from one machine to the next!

It's also interesting to note that even though nothing readily comes up from a quick search, it would certainly be possible to produce a tool (even System Preferences style) that mimics the way .Mac syncs user information by leveraging the same concepts involved with gDisk and other online storage hacks. Such a tool would be very useful because it would provide the ability to arbitrarily sync data such as Keychain items, bookmarks from Safari and other browsers, etc. Keep your eyes peeled; something like this is bound to turn up sooner or later.

Do You Trust Google?

One big question in everyone's mind right now is whether or not Google can be trusted with virtually all of their information. Conspiracy theories run rampant and sites such as GoogleWatch have popped up all over the Net, but there are definitely plenty of Google champions out there too. This interview with Brin and Page provides some topics that are good food for thought, such as what does "Don't be evil" really mean? Who decides what is and isn't evil? Should Google not "taking your email hostage" make you trust them any more or less? It's a lot to think about--and the key is to make sure you are periodically thinking about privacy issues that are important to you.

Since Google is a search company at heart, being able to mine your data is of particular interest to it, so it probably won't be offering to do this anytime soon--but it would be neat to have a suite of tools (perhaps Greasemonkey scripts) capable of performing client-side encryption/decryption on data before it's ever sent to Google's servers. Even a mechanism as simple as a basic cipher would provide a minimal amount of privacy while not overtaxing your browser's JavaScript engine. Anyone?

What Else?

Recalling that our intentions were to discuss how to make a smooth move to a Google-centric online experience as an existing .Mac member, there are a lot of neat Google services that we couldn't talk about simply because they're not on topic. But there is one that you should know exists--not because it's directly comparable to a .Mac feature, but because many .Mac users wish there were a better way to keep snippets of text and other small notes synchronized across multiple machines.

You guessed it. Google Notebook is the Google app (still in the labs) that allows you to manage text clippings like notes and to do items while you're browsing the Web. There's also a great Firefox extension, which some prefer to the Google Notebook interface itself. If you can live with Firefox, the Google Notebook and Google Browser Sync extensions go a long way to make Firefox even more powerful.

You can always review everything Google is cooking up on its products page. As of late, its Docs & Spreadsheets duo have been getting a lot of press.

Is it a good idea to move away from .Mac's paid subscription to a free Google-based online experience? What's .Mac doing right that Google is not and vice versa? Do you trust Google any more or less than Apple with your precious information? Like any other topic, there is always more that can be said, so please share your thoughts below.

Matthew Russell is a computer scientist from middle Tennessee; and serves Digital Reasoning Systems as the Director of Advanced Technology. Hacking and writing are two activities essential to his renaissance man regimen.

Return to the Mac DevCenter.

Copyright © 2009 O'Reilly Media, Inc.