The Sick, Sad State of Windows Apps

Several months ago, prior to the announcement of Windows 8 app store, I tweeted:

What do I mean by “wild west” app store? I mean, isn’t it a good thing we have freedom with the internet to install any app we please?

The freedom is good, we should always have that option to side load whatever we want on our devices. However, the “wild west” model has devolved into a sea of pop-over ads, misleading links, hidden downloads, pleas for donations, and security nightmares.

Let me show you with pictures. (Let’s go shopping!) Today, I want to install one of the best, free Windows apps: Paint.NET. It’s a great photo editing tool, and I want to install it on my new work laptop.

Behold, the state of the art way to install Windows applications in 2011:

First, I’ll open my browser so that I can navigate Windows’ Wild West app store that is the internet. Now I’ll just type in and hit enter.

Umm…looks like I want the one on the left. I think. Grandma probably doesn’t know what to do here, so she’d close her browser already. But me, I’m tech smuggy smug smug smart, and I know it’s the one on the left right.

Alright, is it installed yet? Of course not, silly. We haven’t even downloaded it! So what’s next?

It’s that big green download button, right? I mean, it’s big. It’s green and stands out. And there’s a cute animal with a paint brush in his mouth. And since I’m downloading a paint program, that must be what I’m looking for!


That’s actually an ad. Clicking it takes you to a competitor’s product, GIMP, the popular open source image editing software. Of course, me being all techie in-the-know, I actually knew that. Grandma didn’t, but she gave up already. Her loss. I think.

Ok, where’s that damned download? Oh, silly me, it must be that other big green download button, with the nice big down arrow. For download:

Surprise, it’s not that either!

Haha, oh internetz, you are so funny. You tricked me! You tricked me real good. That big whitespace between the Big Green Download button and the “PDF Creator” label – you sure had me fooled!

Now that I’m aware of my situation of being in a software link minefield, I’ll just look around…

Ah! There we are. It’s no Big Green Button, it’s no Big Down Arrow, but it’s the name of the thing I’m looking for. I’ll just click that…

Erm, well, I thought I was there. But really I’m on some new page that, as far as I can tell, exists solely to show me fine advertisements from the classiest of internet ad vendors.

Ah, this just means I get to play Round 2 of Find the Download link. I know it’s not that Big Green Download button. That silly internetz already tricked me once.

Oh, I know, it’s that nice big yellow button, specially styled with double underlines! That must be it:

I know, I’ll just go mouse to click on it…

Oh noooes! It’s the dreaded Hover Sticky Pop Over. Another fine internet advertisement displays over the page, just by mousing over it! Imagine that, I don’t even have to do anything, and ads come flying at me!

Better yet, the ad is “sticky” — it doesn’t just go away on its own. You actually have to click on the ad (ha!), on that tiny little X button, to close the ad.

Ok, internetz, I promise not to move my mouse. I’ll just move my eyes, then navigate the hyperlink minefield to get to my good download. If I can find it…

Ha! I win! I found your damned download link! Take that, internetz! I may have lost a few battles, but I won the war, I have my download link! I’ll just carefully move my mouse through the whitespace and onto the download link. And now I’ll just click it and…

Wait – this isn’t my download! 🙁

Oh, immortal internetz! You came back for more. Round 3 here I come! I was fooled in the last 2 rounds, but this time I will defeat you, and find my download!

I have learned the ways of the fake Big Green Download button. I now know to avoid that, and avoid the Other Big Green Download button, a internet advertisement warrior who makes his second appearance in Round 3.

I shall not be fooled again! I shall not click you!

And behold, I have spotted what appears to be the real download link! I shall carefully navigate my mouse past the Dreaded Hover Sticky Pop Overs, and I’ve managed to click what appears to be the real link!

Claim Round 3 for the humans!

After a sweaty, multi-round battle for my download, which involved feigned paths down rogue installs, navigating multiple hyperlink minefields, and outsmarting my way past the decoys, I’ve downloaded my software:


Am I done? Have I made it? Is this heaven?

No, silly. We’re only halfway there! So much more fun to come! Now I’ll just click on that zip file. Grandma might not know to do that, but she left a long time ago. (Maybe I should have followed her and taken up a career in knitting?)

Nay! Faithlessness begone! I shall see it through and be victorious. I shall click on this zip file to unzip it:

Oh, shoot. My unzipper isn’t registered. As creepy as that sounds, it turns out I’ve already purchased this software…on my home machine. Windows is too dumb to know that. Now, I could go hunting for my registration key — it’s probably sitting on my home machine. Or in a backup folder. Or a cloud drive. I don’t remember.

Anyways, I’m too lazy. WinRar developers were kind enough to let me use it anyways. I’ll just dismiss this message, and I should be good…

Oh dear. Some UAC prompt. That’s User Account Control, for you uninformed peasants. Even though if I said “C colon slash software Adobe twelve ee en you es dot exe” to my grandma, she’d think I’m speaking in tongues. But me, I’m super techy so I know that just means the path to an executable file.

But this scary prompt about a program harming my computer is frightening. Is it safe?

I’ll just assume it’s safe. Assuming I went to the right website, clicked the right download link, unzipped the right zip file, and launched the right executable, it’s safe. Probably.

Let’s cross our fingers and roll with that. I’m determined to win this victory. I am determined to triumph! I shall click “OK” to the UAC security prompt…

Ah, this looks right! Of course, it could be a phishing attempt. But it looks legit. I’ll roll with it.

Now, what are these options? Custom or quick? Um, what if I just want it installed? Quick sounds good, but what if it’s skipping stuff I need? Ahhh! Too many decisions! Analysis paralysis!

I’ll just pretend I didn’t see those options and click “next”. I hope it works…

It’s installing. I think.

But it’s been installing for about 2 minutes now. The progress bar moves ocassionally, but I’ve seen software where the progress bar just resets to 0 once it gets to 100, so maybe it’s not working.

I’ll just go get some Mt. Dew and come back in a few minutes…

Ok, I’m back from my caffeine and pee break. What was I doing again?

Oh yeah, Paint.NET! My long, drawn out battle is coming to a close! Victory is so close, I can taste it.

But first, more clicking. I need to click “start Paint.NET”. It didn’t start. Oh, that’s right, I need to click done or next or whatever. Then it should start. (I hope?)

After performing lots of clicks on the right elements in the right order, I believe I have appeased the MSI Installation Click gods.

My final goal has been achieved! In as little as…well, time doesn’t matter. In just a few…we’ll, clicks don’t matter. With bold confidence I…we’ll, the whole process invoked uncertainty.

Installing apps for Windows (and Mac) sucks. In 2011, it freakin’ sucks. This is why people are afraid to install native apps. This is why web apps are taking over and native apps are disappearing.

If Microsoft doesn’t fix this with Windows 8, the Mighty Microsoft will go the way of Sun. No one will buy Windows, because OS won’t  matter; everything’s on the web. And if no one buys Windows, no one will buy Office. Microsoft’s 2 big cash cows will dry up like the Negev. Microsoft desperately needs to make Metro apps work.

The App Store model, and Microsoft’s new WinRT/Metro APIs, promise to fix these problems. If Microsoft executes well, they’ll make Windows apps relevant again, and Microsoft will survive. If they fail, you’ll see a decade’s worth of corporate reinvention, perhaps the largest reinvention in history of the world.

All eyes on Windows 8.