MobileMe and Gmail: Pick one or expect frustration

mobilemegmail.jpg

There are certain fantasies that I try to forget: cheap solar batteries in every device; a wireless, Model M clone keyboard with a Macintosh key layout but real buckling springs; that one with the octopus and I think my hair is in a bun?

And that one that Apple just triggered again with MobileMe: all my data, email, contacts, scheduling, and media accessed and synced through a single sign-on.

I signed up for the MobileMe trial on the day it was opened to the public, if only to grab my preferred username. Still, perhaps I could make the magic happen. I’d always been intrigued by .Mac, but had never been compelled to pay $100 for a service that Apple put out to pasture.

Bear in mind that I am not a heavy calendar user, although I always feel like I should be integrating more tools into my organizational system. (I recall telling a friend a few weeks ago that I read 43 Folders primarily because I liked reading about tools, not because I had any hope that I’d implement them with any discipline.)

So my needs are modest: email, which doesn’t even have to be push-to-the-minute; a few appointments here and there, very infrequently added from my phone instead of at my computers; a unified list of contacts; a virtual drive for backing up important files; a place to store and share my photos.

I’ve found that as a heavy Google user, Mobile me is not a terribly good fit, despite owning both a Mac and an iPhone.Email
This isn’t to say that there’s anything inherently flawed about MobileMe. In fact, were I willing to sacrifice just one thing — my @gmail.com email address and the accompanying archive-for-life storage — I could probably switch over to MobileMe without much of an issue.

Unfortunately, MobileMe is still built around the notion that you’ll be using your @me.com (or the still-functional @mac.com) address as your primary online identity. As a long-term Gmail user — I’ve been in since the Beta! — I’m not about to ditch it for a MobileMe address.

What I thought might have been possible would be to use the @me.com address and the accompanying MobileMe email interfaces (iPhone, Mail.app, and the Me.com webapps) as a sort of shadow account to my Gmail. I’d simply forward my Gmail to my Me.com account, then set the Reply To field to reflect my Gmail account. That wouldn’t send my outbound mail through Gmail’s mail servers, but it would route any replies back through before they were forwarded to my Me.com account. As long as people copied my replies in their replies, there would still be a copy of many of my outbound messages in Gmail for permanent archiving.

Sadly even this imperfect solution was not to be. While Mail.app allows you to change the Reply To field in all your outbound messages, the Me.com web app and the iPhone email client do not. Unwilling to commit to splitting responses between two accounts or to switch over entirely to the Me.com address, I stopped my Gmail forwarding bit after just a couple of hours.

Calendaring
The Calendaring synchronization works fine, although it’s still limited to a one-way connection from Gcal. You get Gcal data from an iCal feed, but iCal.app, the Me.com Calendar web app, and the iPhone Calendar can push appointments back up to Gcal.

This was actually one of my major hopes for MobileMe: It would be nice to start relying on my phone as the input device for all my life’s scheduling instead of making notes and adding appointments later on my laptop or accessing the mobile interface to Gcal on my iPhone EDGE’s Safari web browser. Again, this is less of a limitation with MobileMe and more of a limitation of my expectations. If I were willing to give my calendaring over to MobileMe completely I’m sure it’d work just fine.

One quirk remains in iCal.app + Gcal whether you use it with MobileMe or as a standalone application: While you can subscribe to multiple iCal feeds in Gcal, when you subscribe to Gcal’s iCal feed in iCal.app (try to keep up!) only your primary appointment feed is pushed down, not an aggregate of all the subscribed feeds. This isn’t an iCal.app failing, but one from Gcal. I don’t know why Google doesn’t let you push down an aggregate feed instead of having to subscribe to every iCal feed twice, once in Gcal and once in iCal.app.

Contacts
I keep all my contacts in OS X’s Address Book.app. Works great — and works essentially the same in MobileMe. Making a change on the iPhone’s contact list automatically syncs the changes back to my local Address Book.app database via MobileMe. But this already works with a tethered iPhone each time you sync, so unless you really needed it to update contacts instantly — and I don’t — it’s not a killer feature for MobileMe.

iTunes actually lets you sync Google Contacts to the iPhone without MobileMe at all, but I keep a separate address book locally and on my iPhone than I do from my email. I’ve thousands of contacts in my Gmail account; I don’t want them all on my phone.

Photos
I use Flickr.

iDisk
My only need for iDisk, the online storage component of MobileMe, would be to backup text files and other important documents automatically. I don’t want to use the iDisk simply as a remote drive since I don’t need to access those files from multiple other places.

My highly subjective preference would be for iDisk to work as a modestly sized web-based Time Machine drive.

What I’m doing now
I can’t stress enough that MobileMe is failing me because I’m not willing to do what it’s asked, which is to leave behind my other web-based services from Google and Flickr. I doubt I’m the only Gmail who would have liked to have incorporated push and over-the-air syncing to their life which is why I’m writing about it now, but complaining that MobileMe doesn’t address my needs perfectly would be much like my father at the Peruvian restaurant the other night, complaining that “everyone thinks they’re Bobby Flay” and should simply learn to “make a freakin’ burrito.”

The good news is I can get pretty close to the services offered by MobileMe, minus the nearly instant over-the-air syncing, with a collection of third-party tools. Gmail works fine in both Mail.app and the iPhone mail application, although on both my laptop and my iPhone I prefer to simply use the web-based version of Gmail instead of IMAP.

My Gcal pulls through iCal.app onto my iPhone just fine. But the addition of Spanning Sync ($25 a year; $65 lifetime) will sync up all my calendars in both directions. I held off buying it forever, but it’s time to pull the trigger.

My contacts, as I said above, work just fine with iPhone and Address Book.app. I don’t sync them back to Google in the first place.

As for photos, before the iPhone 2.0 firmware was released I was using an jailbroken application called “iFlickr” to automatically push photos up to Flickr from the iPhone. It didn’t always work and would sometimes duplicate uploads so I wasn’t sad to see it go. Now I’m syncing back to Flickr from the iPhone manually by importing the pictures through iTunes to iPhoto, then manually uploading the ones I want to share. That’s really awkward.

I’m surprised there aren’t any applications from the iTunes App Store that duplicate the functionality of iFlickr. Fraser Spier’s excellent Exposure application for iPhone 2.0 is a fantastic interface into Flickr but inexplicably doesn’t allow you to upload to Flickr from the device. Surely this will be remedied soon, if not in Exposure then in some other dedicated “iPhone to Flickr” application.

Because of the way I use Flickr these days — primarily for sharing, not for archiving — I’m not overly concerned with keeping every last photo in my library in sync between my computer, phone, and the web. Mostly I just want to be able to instantly upload a picture from my phone to Flickr for sharing.

Twitteriffic for the iPhone will let you upload a bit to Twitpic.com, however, but I’d still prefer to use Flickr to keep the picture in my collection.

In short, I’d be perfectly happy to pay $100 a year for over-the-air syncing if MobileMe allowed me to use other services than those from Me.com. But that’s not what they’re selling, so I’ll just have to go without.

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22 Responses to MobileMe and Gmail: Pick one or expect frustration

  1. qousqous says:

    Shozu also looks to be a good solution for uploading pics to Flickr (as well as interfacing with a number of social networking sites).

  2. mishadotcom says:

    Since Gmail hasn’t always offered IMAP, I have been routing my Gmail through my .Mac mail for a while now and it works flawlessly. The difference though, is that I am not using a “Reply to” field to determine my address when sending. Rather, I changed the SMTP info to be that of Gmail, while the incoming info was that of .Mac. It is still working under MobileMe and I am now getting push Gmail to my iPhone. Here’s a link to more info about the process: http://www.mikeindustries.com/blog/archive/2006/04/how-to-use-gmail-over-imap

    Hope that is of some help/made some sense.

  3. Christopher Vigliotti says:

    I’m a Google head like you. After reading this I’m glad that I didn’t pickup an iPhone.

    I’ve downloaded the SDK + emulator of Google’s Android OS and after writing a sample app and checking out the features + interface I can say that I’m genuinely excited to get an Android Phone.

    I’ll save the MobileMe for MobileThem.

  4. qshio says:

    The hang up for me is that you can’t utilize the SMTP fix in Gmail when using MobileMe’s web interface – or at least I don’t see how. If you want to integrate the whole thing into one service, and not go back to Gmail on the web when away from your home computer, MobileMe, as far as I can tell, will not allow you to reply as though from your Gmail account from the web app.

    Please, please correct me if I’m wrong.

  5. Anonymous says:

    The Iphone app AirMe will upload pics to Flickr.

  6. Joel Johnson says:

    #2 You’re right: You can select the @gmail account as the Reply To field if you have both accounts set up, but there’s no way to make that the default setting.

  7. hemidemisemiquaver says:

    As a long-term Gmail user — I’ve been in since the Beta!

    Gmail is still in beta.

  8. SimeonW says:

    I think it may to too soon to tell how well MobileMe is going to work. It is also too soon to tell what additional functionally of the kind Joel needs will show up in the App Store.

    My PowerBook is out for repairs, and I have been trying to use me.com from various computers, to access my email, calendar, and address book. So far, my me.com experience has been a training exercise in patience and acceptance with things that do not work.

    That said, I expect these server issues and other functionality problems to get ironed out quickly, just like I expect that many of the earlier jail brake apps, or their equivalents will show up in the App Store.

  9. Anonymous says:

    You can set your iPhone/iTouch to use gmail and not MobileMe – just go into settings and turn off the MobileMe email (this is what I do, I never use my .mac email). I agree the $100 is high and most people probably won’t use it. In fact the people most likely to use it (students at university) probably can’t afford it. I’m a graduate student myself and I find it right handy, personally. My laptop, desktop, and iTouch are all updated automatically (vital for my calendars, I’m no longer telling my students to email me at home so I can check my most recently updated calendar) and anything I write on either system I can drop in iDisk and then print out at the university (where I have free printing).

    Ultimate verdict? Great for some people, but that body of people is rather wee.

  10. jangohollywood says:

    I’ve read a few of these MobileMe vs Gmail debates because I’m an avid Gmail user, but I’m also a fan of the Cloud system that Mac has launched and will undoubtedly be improving over months to come. I don’t think it has to be an either/or debate. Read on:

    I have several Gmail accounts: one personal, one for online accounts, and others for my different shades of professional endeavor. The latter may sound like excess, but I manage these fluidly with filters and forwarding.

    So why would I give this up just to take advantage of Push technology? I’m also a huge fan of 43 Folders and Merlin Mann’s Inbox Zero, so adding another domain to my Gmail system initially reeked as clutter.

    But then I realized, do I really want to manage all of my Gmail from my iPhone, via push technology? Or could the iPhone contribute to my Inbox Zero email management? The answers, respectively, NO! and ABSOLUTELY!

    The solution I’m about to describe (which I believe to be quite elegant) might not work for everyone — but I think it’s the bee’s knees.

    Simply by setting up filters in my Gmail account, I can forward the most important email, the most likely email to need immediate response (which isn’t much), or email from close friends and family to my MobileMe account. It’s simple to let those “inner circle” contacts know what’s up with the @me.com address, if they notice at all.

    Then when I am back at my computer, I know which email—the most important email—I’ve already read or replied to. This makes it much easier to scan whatever else is waiting for me, that second tier of email.

    This filter system works great for me, and it’s organic. It can grow as my needs or wants change, and IT’S NOT all or nothing. It allows my iPhone and MobileMe to become an effective part of my email management. It also gives me the peace of mind that if my iPhone indicates a new mail message, I’m not going to open it up and find that forwarded joke from Aunt Millie or a solicitation or a distant hello from a former colleague.

    ALSO: You can mask your email outgoing from your iPhone to appear to be sent from Gmail. Check David Berube’s Blog for details.

    Hope this helps a few folks seeking to avoid the bipartisan Gmail vs MobileMe debate!

    Best,

    GLW, Jr

  11. crimefighta says:

    don’t know if anyone is going to see this since this conversation is a few weeks old, but i’ve been toying around with solutions and came up with the following.

    first caveat. i am not smart. i dont know diddly about this stuff.

    but, i have my gmail account and my mobileme account both on my iphone because i was part of the 1% that was w/o mobileme email for an eternity (strike one apple). when mobileme came back, i went into mail settings and just turned the gmail account off — before that, i had gmail turned on (with fetch every 15 min), mobileme mail turned off, but kept calendar and contacts turned on for sycning purposes. not perfect, but fine.

    im forwarding my gmail to my mobileme because i like having the push feature so much on my iphone3g and need to get emails quickly. however, when i reply, yes, my emails say they’re coming from my mobileme address. bah. again, not perfect.

    but i went into mail settings on my iphone, selected my mobileme account, and changed my outgoing mail server to the google one (in my mobileme account settings i can select smtp.gmail.com as outgoing mail server). I send emails now and they go back out through google (from my mobileme account on my iphone) with my @gmail.com address as the sender. i use mobileme sync for my calendar and my contacts (could even use spanning sync if i really wanted true gmail/mobileme integration) and all seems pretty alright.

    although, i do agree that this network of proprietary systems that are a pain in the ass to get to work together is inelegant, inconsiderate of the consumer, and ultimately, pretty schizophrenic.

  12. TerribleTwos says:

    I have been playing around with the iPhone 3GS and I wonder if Apple has fixed the MobileMe stuff at all so it syncs better with Gmail. I run a few websites and I ordinarily forward all my customer emails to gmail, and I like to be able to reply quickly from whatever email account (POP usually) that the customer’s email originally came into.

    Anyone know if this has improved?

    Chris Thompson
    http://www.TalkingToToddlers.com

  13. lia says:

    Now I’m syncing back to Flickr from the iPhone manually by importing the pictures through iTunes to iPhoto, then manually uploading the ones I want to share.

    jesus, dude, that’s ridiculous. why aren’t you just uploading through email like everyone else?

    http://flickr.com/account/uploadbyemail/

  14. Chris Furniss says:

    I just email my photos to flickr with the iphone, just as Lia up there stated. Works like a charm. You can even add tags and such.

  15. dssstrkl says:

    I’m going to second the notion for Busy Sync. I used it for about a day before a bought a license, its just that useful to me. I’m not quite sold on mobileme yet, but it does work really well with busy sync. The combo even gets my calendar’s colors right.

  16. Thomasina says:

    “My Gcal pulls through iCal.app onto my iPhone just fine. But the addition of Spanning Sync ($25 a year; $65 lifetime) will sync up all my calendars in both directions. I held off buying it forever, but it’s time to pull the trigger.”

    I was contemplating Spanning Sync, as well as the competitor BusySync, until I discovered that Google offers the facility to sync calendars with iCal (that’s right, synchronize not just subscribe) for free, via CalDAV support. This works really well for me and doesn’t require the use of a 3rd party app.

  17. Joel Johnson says:

    FINE I WILL DO THAT THEN SHEEEEESH. (Thanks.)

  18. zuzu says:

    Such is the problem with the “walled garden” implementations of all of these “Web 2.0″ “web applications”.

    The Internet of yore solved these problems by emphasizing protocols and statelessness through asynchronous message-passing concurrency. e.g. SMTP, IMAP, HTTP (later extended as WebDAV), etc.

    Unfortunately, as soon as the “web developers” (formerly webmasters) took over, with their quasi-Art school quasi-IT subculture, we get crap like AJAX — taking a giant leap backwards to pre-networked “desktop applications” where we came from in the 1980s. Suddenly statelessness was a “a bug, not a feature”. Personal data has been centralized into warehouses such as Google, Microsoft, MySpace (i.e. NewsCorp), Facebook, Yahoo, etc. to do who knows what (or resold to Acxiom or ChoicePoint). We no longer run servers from home to publish our “home page” with pictures, video, code, or run our own mail servers (because whiners complain about the phantom menace of “spam” like censors and authoritarians would shriek “think of the childrens!” or “terrists!”)

    Now we begin to recognize the dark side of this “AIM or MSN or Yahoo” mentality (or was it “CompuServ or Prodigy or GEnie”?) of centralized remote hosted webapps.

    What we’ve really been longing for is orthogonal persistence using open protocols developed and standardized via RFC.

    (Now get off my lawn! :p )

  19. Zandr says:

    BusySync also handles the gCal/iCal sync problem, for $25 once. It’s licensed per-computer, not per-person, but if you have a machine on all the time, you really only need one license to maintain sync, as MobileMe handles sync between iCal on multiple macs.

    No affiliation, just a workaround I found.

  20. phi says:

    If you’re uploading photos via the email, they resize the photos from the 2 megapixel 1600×1200 rez down to 640×480 crap. If you’re running a jailbroken 1.1.4 phone still, SendPic will get around that issue, but I don’t know if that exists on 2.0 yet or not.

  21. Anonymous says:

    Its now a year later and Google and added significant synching capabilities. MobileMe has also added features although I’m not familiar with it.

    Given Gmail and MobileMe’s features today what would you do?

  22. Anonymous says:

    You can still forward your Gmail messages to your @me.com address and, when replying from your iphone with 2.0 firmware, select your @gmail.com address as the account to reply from. It works perfectly.

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