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Thursday, 10 January 2008 10:26

The Road from Windows - Online email

My quest to abandon Windows for Apple's Leopard or Ubuntu's Gutsy Gibbon has become a quest to abandon desktop software, but I'm yet to find an online email client that gets a tick in every box.

A hard drive failure 12 months ago forced me to rethink my email system and my reliance on Gmail, POP3 and Outlook 2003. I decided to switch from POP3 to IMAP so, if I had another hard drive failure, I wouldn't be forced to re download my entire inbox just to recover the last few days worth of mail. Gmail didn't support IMAP at the time so I moved to FastMail.fm.

The problem I encountered is most IMAP email clients only download the headers until you actually read an email, which is a pain if you need to find something in your inbox while you're offline. A lot of IMAP desktop email clients claim to let you automatically download the entire email but the feature often doesn't actually work (or doesn't work with sub-folders).

I think the only email clients that would do the job were Outlook Express and Thunderbird 1.5, when combined with the Sync on Arrival plugin. I opted for Thunderbird, because it has better features than Outlook Express and it's multi platform. Frustratingly I haven't been able to upgrade to v2.0 because it won't work with Sync on Arrival.

Thunderbird runs on Windows, Linux and Mac, which makes it easy to switch between platforms, but I've noticed that Sync on Arrival doesn't seem to work with all sub-folders runningThunderbird 1.5 on Leopard. To be honest I'd really like to wean myself a desktop email client completely, which would obviously eliminate my syncing issues. Of course this means I'll need internet access where ever I go, but Australia's current mobile data price war means this is finally feasible. Of course the irony is that if I'm always online then I don't need to worry about Sync on Arrival.

As with online calendar applications, one of the biggest hurdles with online email clients is finding something with decent desktop pop-up notifications. I find detailed email pop-ups offer a major productivity boost because you can quickly see if an incoming email is important without the need to switch applications.

I've come to the conclusion that you really need some kind of desktop notifier/messenging app to produce decent pop ups, even though it goes against my efforts to free myself of desktop apps. The need for a desktop notifier for my webmail narrows down my options to the usual suspects such as Google, Yahoo and Windows LiveHotmail. The third party FastCheck notifier works with FastMail, but it's not as fully featured as the other apps. The fact it hasn't been updated for more than two years doesn't fill me with confidence that we'll see a new version any time soon.

FastMail is highly regarded in the industry as an email service provider and I've been very impressed with the service over the last 12 months, but I wouldn't want to useFastmail's webmail as my primary email interface. I want something that looks like a desktop app with the Outlook-esque three window view (folder list/email list/preview pane). I also want web interface that automatically refreshes the page when a new email arrives, using something like AJAX. While I'm making demands, I also want a decent mobile/WAP interface to use from my i-Mate JasJam smartphone.

FastMail's web interface is completely text-based, which is great for low bandwidth (or expensive) wireless connections, but it doesn't automatically refresh the page. It also lacks a preview pane, although it can be set to show the first few lines of each email. The mobile interface isn't bad, but it's not as user-friendly as Gmail. So why not use Gmail? CONTINUED

Gmail is also completely text-based, and it does use AJAX, but I just don't like the Gmail interface. I know I'm stuck in an Outlook mentality, but I want folders. I also want a proper preview pane, and I don't like the way conversations are threaded. Now before the Google fanboys embark on a flame war, I'm not saying Gmail is crap. It has a lot of useful features, but I just couldn't work with it all day every day.

Along with folders, I want server-side filtering rules rather than relying on a desktop client to sort incoming emails into the appropriate folder. This is one of FastMail's many strengths. Again, I'm certainly not saying Fastmail is crap and I would definitely suggest anyone looking for an online email service evaluate FastMail to see if it meets their needs.

I know I want to have my cake and eat it - I want all the advantages of webmail without sacrificing any of the functionality of a desktop client - but I'm still entitled to have my wish list.

That would appear to leave me with Yahoo! and Windows Live Hotmail, both of which I've used for more than a decade. They're both blessed with big inboxes and decent messaging/notifier apps. Thankfully it's possible to use your own domain names with such accounts, because using a Yahoo! or Hotmail account for work doesn't really create a sense of professionalism.

At first glance Yahoo!'s new AJAX interface would seem to be everything I'm looking for, combined with a fully-featured desktop notifier/messenging app. I really like the use of tabs, so I can have multiple emails and folders open in the one browser window. I also like the inclusion of an RSS reader (something for another post).

For me Yahoo!'s major shortcoming is that you're only allowed up to 15 filters/rules. This might not bother most people, but I use 45 rules in FastMail to sort incoming newsletters and press releases into various folders to reduce clutter in my inbox. I know I'm being fussy, but my filtering rules are all that save me from email overload and without them my productivity would surely drop.

Windows Live Hotmail has similar issues, with a limit of 15 rules. I don't know if these restrictions are lifted if you opt to pay for a Pro account, I'll have to look into that. In theory Windows LiveHotmail's default three column layout should show more on the screen at once than Yahoo!, which surprisingly can't be changed to move the preview pane to the right rather than under the email list. Windows LiveHotmail's layout advantage is negated by the fact Windows Live Hotmail dedicates a lot of space to displaying the message header. To be honest, I also have to say I have some trust issues when it comes to putting my life in the hands of a Microsoft service.

So Yahoo! looks the best of the bunch, but it still doesn't look quite right for me. Is that it?
<Yoda>No. There is another...</Yoda> 

As I've said recently, I'm leaning towards buying a Mac Book running Leopard so there's also the option of a .Mac account. Of course you don't need to own a Mac to have a .Mac account, but to be honest I wouldn't have thought of it were I not considering buying a Mac Book.

A .Mac account costs a hefty $US100 a year for a 10GB inbox, but of course you're buying into the whole Apple lifestyle. It ties nicely into the Mac ecosystem - such as web publishing, blogging and podcasting with iLife. Thankfully there's a 60 day trial so you can really put it through its paces before handing over any money.

The .Mac interface looks exactly like the Apple Mail desktop app, so the preview pane is under the email list and there's no option to switch to a three column layout. Unfortunately Apple doesn't offer a desktop notifier app but there's a few third-party widgets that will do that job.

The .Mac account naturally plays nicely with the Apple Mail desktop app, although I was astounded to discover that Apple Mail doesn't have pop-up notifications. The free MailAppitizer plug-in rectified this.

The biggest disappointment with the .Mac account is you can't set filtering rules in the webmail interface. Filters can be created on the desktop in Apple Mail, but they won't be run until you check your email using Apple Mail - which is useless if you're trying to forgo desktop apps and just use webmail.
While .Mac seems to have a lot of potential, the lack of online filters is certainly a deal breaker. For now it looks like I'll be switching to a Leopard Mac Book and running a desktop mail client to download from FastMail. Disappointingly Thunderbird 1.5's Sync on Arrival plugin didn't seem to work properly on the Leopard Mac Book Pro I tested it on, but Apple Mail seemed fine with my FastMail account using IMAP.

After all my ranting about using multi-platform apps it looks like I'm getting sucked into Mac world with Apple Mail and iCal - but I'm after the best tools for the job so I can't let stubbornness or ideology get in the way. At least it's easier to import and export data from these apps than from Microsoft apps, so I'm not locking myself in - as I was in Windows world. I haven't given up on my dream of an app-less desktop, so I'll keep an eye on Fastmail, Yahoo! and .Mac's webmail offerings in the hope that one day I'll find something that gets a tick in every box.

The Road from Windows - Time for change

The Road to Leopard or: How I Learned to Stop Worrying and Love the Apple Mac

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