I’ve been using a Windows Powered PDA (off and on) since the very first one arrived ten years ago (The Everex Freestyle). With a few exceptions I’ve tried to be a loyal fan but took a few side trips to Nokia (Communicator 9210), Danger (Sidekick) and RIM (Blackberry 7290). At one point in time I even tried a SonyEricsson P800 and a Nokia e61, but I’d rather not talk about that…

I’ve always ended up back with a Windows device. To me, it’s the combination of good hardware with a decent OS that entices me. But there are some cracks in the foundations. I’m becoming more and more aware of how dated Windows Mobile has become. So it’s time to look at the top 10 things that suck in Windows Mobile.

I’m going to base this article on WM6.0, I know 6.1 is on the way, but with 6.1 very little will change, so this article still applies.

1. The program manager

The program manager shows all the applications you have installed.

There is no customization possible. You get icons, 3 wide, one size, and that’s it. It’s like communism took over the development department.

In every (desktop) version of Windows you can change the view (icons, list, details) and even sort or rearrange things. Not under Windows Mobile. There are some replacement program managers, but none of them really integrate perfectly into the OS.

If you have a lot of applications installed you’ll constantly be scrolling up and down. Experienced users can manually create folders for their applications (tools, games, multimedia etc) but stuff like that should have been made easier.

2. Connection manager

The Windows Mobile Connection manager is a turd. It’s purposely made to piss you off. Simple things like editing an existing connection are made overly confusing. If you arrive at a hotel and want to connect to the wireless network, you’ll be screwing around for 10 minutes trying to figure out just what the hell your phone wants from you.

Compared to the WiFi manager on the iPhone, connecting on Windows Mobile is like trying to perform open heart surgery with stuff you learned on Wikipedia.

3. Internet Explorer

This is one of the main reasons people love their iPhone. Safari on the iPhone is great. It renders nicely, it’s readable, it is efficient and fun to use. Pocket Internet Explorer is about as much fun as a wet fart in your space suit.

It’s slow, it doesn’t load anything right, navigation is a pain and it has fewer features than your average tin can. There are no tabs and even the simplest of enhancements requires another (paid) thid party application.

Thankfully other companies (like Opera) understand the needs of mobile users and offer a very decent alternative browser (there goes another $24).

4. Pocket Outlook

Another example of an application that someone forgot to update. There are no filters, no spelling checker, there isn’t even an option to mark all email “read” (unless you install a third party hack). You can’t even delete all your emails without manually selecting them (yeah, there isn’t even a “select all”).

Pocket Outlook shows you email. And that’s it. You also can’t read HTML emails unless you are connected to a recent version of Exchange for your (push) email, and even then it’s pretty useless. Once again someone put effort into making this application as useless as humanly possible.

5. Text entry/keyboard

Look at these two soft keyboards. Can you tell me which one was made in 2001, and which in 2008?

Don’t bother answering, because both of them are exactly the same. Whoever is in charge of making sure we users can enter emails or messages should be taken out back and put out of his misery (or just fired).

6. Performance

The first Windows handhelds (Everyex Freestyle, Casio Casiopeia and Philips Nino 300) ran around 66MHz. My current machine runs on a 400MHz dual core Qualcomm cpu, but it doesn’t feel any faster. There is still a noticeable lag when you do stuff. Every now and then something in the OS gets tired and decides to take a little break. You’ll press a button and somewhere in the phone a line of program code is napping.

7. Memory

Can’t really blame Microsoft for this one, but why on earth do vendors STILL insist in selling these devices with just 64Mb of memory? On my Sprint Mogul I have a “whopping” 18Mb available without even doing anything (on a completely clean device, with no applications). By the times I’ve opened IE and Outlook I’m down to 2Mb of free memory.

But Microsoft is not completely free of blame here. They should start setting standards for their device manufacturers. Just like the “ready for Vista” program told companies that they’d need to sell PC’s with 1Gb of Ram, the Windows Mobile team should come to the conclusion that their bloated OS doesn’t run well on 64Mb of Ram.

Then there is the “memory leak” which every Windows Mobile device seems to suffer from. Even when you don’t use your device, it’ll slowly eat memory, to the point where you need to run a third party application (like Oxios Hibernate) to reclaim that memory. If I put my phone down at night, I’ll have lost 10Mb of precious memory by the morning.

8. Software/Firmware updates

On my desktop I click “windows update” and the newest version of stuff comes to my PC, no matter what brand of machine I’m using.

On my PDA I have to wait for the manufacturer to finally get around to issuing an update, or turn to resourceful hackers that fixed stuff for me.

My previous device (the HTC TyTN) didn’t get an update for broken stuff till 9 months after it was released, and even then it didn’t fix everything.

And even when updates DO come out, every operator has their own version. So; my TyTN was updated, but customers on Cingular with an 8525 (the same phone) didn’t get that update till 4 months later. Pathetic.

Microsoft need to wake up and fix this before doing anything else. Users should not have to wait for the device manufacturer to get around to issuing fixes.

It’s like Dell telling their customers that the super important hotfix for that nasty bug in Vista won’t be available to them, even though people with an HP or Gateway got it 3 weeks ago.

At one point some resourceful fellow clearly understood this problem, because a “windows update” application is built into Windows Mobile 6. But they have never issued any updates through it, and nobody really seems to know why it’s there.

And to make matters even worse; when you do finally get an update, it deletes everything off your device (all your apps, emails, contacts etc.). There are several ways to make a backup, but those all involve commercial applications and are not recommended for making restores after an update (they often overwrite the new files).

Activesync can restore some of your stuff, but things like connection settings, themes, ringtones and every other personalization setting is lost. On average, a firmware update takes me around 2 hours from start to finish. Imagine going through that every time you get an update for your desktop computer.

9. Look and Feel

Sure, it’s just a calculator, but would it hurt that much to hire a graphics designer and clean up the damn thing? On the iPhone they actually used inspiration from 1960’s German designs (Braun) and made a sleek and clean looking calculator. On Windows Mobile they took something from a 1982 Basic program and hit it a few more times with the ugly stick.

Virtually everything about the OS feels badly designed.

Buttons and options are in strange places. For example; if you want to turn on the option to receive incoming Bluetooth file transfers, you go to settings, power, menu, beam.

Why they decided that “power” would be a good place to hide this is beyond me. I’m guessing they wanted the least obvious place.

Then there are features that should work perfectly, but never do; like syncing the phone over Bluetooth (rarely does anyone accomplish this) or WiFi (not possible at all).

10. Support

Put simply; support from Microsoft SUCKS. Features are added or removed but nobody at Microsoft seems to know about them (or care).

Last year the ability to use Dial Up Networking over Bluetooth was taken away. The year before that it was Activesync over WiFi. There is no communication from them, other than an occasional blog post explaining why they think they did the right thing.

It’s almost like the entire OS is being developed in someone’s basement. The Windows Mobile team is completely disconnected from their user base.

For example; almost every Windows Mobile device with Bluetooth uses the Microsoft Bluetooth drivers.

But for the past 4 years most of it seems broken. Bluetooth Stereo usually sounds choppy, and most devices see random disconnects. But nobody at Microsoft has ever addressed those issues, and even the most recent devices are still being sold with a crappy Bluetooth stack. Some phones ship with Bluetooth file transfers (OBEX) turned on, others don’t. It’s one big mess. My tip to them: take control of the situation and fix it. It’s so bad that users pledged thousands of dollars last year to any developer that could port a third party version of a Bluetooth driver to their phone.

Final thoughts

It’s not all doom and gloom. There are some things on Windows Mobile that actually work quite well. Push email (using Exchange) is snappy and reliable. The devices themselves are also stable and rarely crash (compared to one or two generations ago).

But what makes a Windows Mobile device usable isn’t what Microsoft did; it’s what third party companies do for it. Without these applications I would have dumped the platform years ago.

There are even some things Windows Mobile devices do better than any other device; Multimedia is one of them. Sure, the iPhone may have a snazzy iPod style interface, but it’s still only going to work with iTunes and a few (limited) formats of music and video.

But my Windows Mobile device plays almost any audio format, as well as almost any popular video file I put on it. The hardware (phones) also pack more features.

We’ve heard rumors about the new Windows Mobile 7, due in 2009, but I’d suggest that they hurry up, or they’ll lose even more market share.