I’ve been using Gmail since its inception and I’ve used it (the web interface) as pretty much my sole email interface for the past 18 months. During that same time I’ve been pretty much solely a Mac user and when I recently bought an iPhone 3G I thought it would be an opportune time to revisit the possibility of Apple Mail, Address Book, iCal since those integrate with their iPhone counterparts and synchronize with MobileMe (née .Mac).

Punchline is: a few days into the process I have decided not to use Mail App nor the iPhone counterpart. I am using Apple’s Address Book (with MobileMe synching). As for Calendar App vs. Google Calendar I’d say the jury is still out. Here’s what I’ve found…


I wanted to continue routine all my email through Gmail in case the exercise went squirrely. Also I definitely wished to retain my Gmail email address as opposed to switching to a MobileMe one. No problem, Gmail offers an IMAP interface and the Apple mail apps both support IMAP too. One thing I found confusing was that the notion of synching email (via MobileMe) didn’t make much sense. My friends tell me that what is actually synched in that case is mail preferences and settings. The actual email messages are not synched per se since SMTP and IMAP do that job for you.

One thing I really like about Gmail is that I seldom delete emails. I delete emails forwarded from Google groups since I know they are archived on the groups. Basically I delete most stuff that I know is archived and available elsewhere. Also if someone sends me huge photos, I’ll download those to iPhoto and then delete the message. In this way I have managed to use “only” 390 MB of the 6943 MB available to me on Gmail. That’s 5%.

It is not obvious how to continue this practice using the IMAP interface. Some searching yielded a solution: to archive a message from Mail App, just drag it to the “[Gmail]/All Mail” folder. This has the same effect as archiving the message via the Gmail web interface. Problem solved.

Gmail threading is a necessity for me. The iPhone mail app doesn’t offer threading, but Mail App does. Just turn on “organize by thread” in the View menu. If the threading on Mail App worked more like Gmail’s then this would probably be acceptable since I use the laptop for heavy email use anyway.

The problem is that Mail App has a different idea of what threading means (versus Gmail). In Gmail the thread is the fundamental unit. This is not so in Mail App. In Gmail, you can archive a thread. If a new reply arrives on that thread then the whole thread returns to your inbox. This is not the case with Apple Mail. With the latter threads do not span “folders”. So once you archive a piece of a thread (one or more messages), when new messages arrive on that thread you will not see the older ones reappear in your inbox.

One of the truly great outcomes of adopting the threaded approach to email is that you eliminate the need to include original messages in your replies. In fact when you do this, Gmail hides the originals (“folds” them for you). If you assume that your correspondents are also using Gmail threading then it is never necessary to include complete originals in your replies. You end up quoting only small parts of originals and even that isn’t very frequent. So when you look at a thread it’s nice and clean. No redundancies in the replies.

A key Gmail feature that supports this approach is that the thread shows not only messages sent to you but also messages you’ve sent. Without the messages you have sent it can be hard to follow the thread (e.g. if you read it a week later). Because Apple Mail does not “knit” threads back together across “folders” and because messages you send are relegated to the “Sent” folder, you will not see messages originated by you integrated into your threads.

Gmail threading, with its elimination of redundancy and its ability to resurrect full-fledged threads when new messages arrives is critical for me. As a result I’m sticking with the Gmail interface for mail both on my Macs and on the iPhone. On the iPhone I’m using Google’s excellent integrated Google.com for the iPhone. That gives me iGoogle, Gmail with threading and Google Calendar all with iPhone optimized interfaces.


All my contacts were in Gmail before getting the iPhone. Since then, I’ve exported them (as .vcf) and imported them to Address Book on the Mac and synched them down to the iPhone Address Book. I’ve configured address book synchronization via MobileMe. Also I set Address Book on my Mac to synch with Gmail (a feature that appears in Address Book after you’ve docked the iPhone for the first time).

Since then I’ve been combing through my contacts using the Address Book app on the Mac and the iPhone one too. Also since my contacts are now driving not just email, but the Phone app as well I’m cleaning up lots of first name/last name issues and consolidating duplicate records. It’s taken a bit of clean up since for some reason there are many duplicates.

This all seems to be working. And it is truly magical to tweak contact information on the iPhone and then see it magically updated (over the Web via MobileMe) on the Mac and in Gmail contacts. I don’t fully trust it yet since there are so many moving parts but the early signs here are very good.

I now have complete contacts available now via Gmail, Address Book App (on the Mac), Address Book App (on the iPhone) and in the Phone App on the iPhone too. It’s often bugged me that Google has not made contact management a first-class application. (I’m continually digging through links in Gmail to get to my contacts). Now I’ve got first-class contact management at my fingertips on my phone and my non-phone computers and it’s integrated not only with email but my telephone as well. This makes me very happy.


I’ve set up MobileMe synchronization on iCal calendars but haven’t tried to synchronize between Google Calendar and iCal. Jury’s still out on this one. Essentially I have two calendaring systems at my disposal now. Both Google Calendar interfaces are darn good. There’s the general-purpose browser-based one and the iPhone-specific one mentioned earlier. Since calendar is much less critical for me than email and contacts I suspect this one will simmer for a while.