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.

Author: Judah Gabriel Himango

I'm Judah: disciple of Yeshua, technologist, builder of things that produce goodness. I blog on the intersection of Judaism and Christianity at I'm the creator of

20 thoughts on “The Sick, Sad State of Windows Apps”

  1. Hey Judah,

    I have absolutely no interest in a stinkin’ tablet computer that all the social media darlings keeping going on about, but;

    I have been thinking for a while, that free and open source apps need an app store. Keep the apps free, but have an opportunity for users to buy documentation, training and other extras, could fund it.

    Often some of the best open source apps stay a secret, and you can only get to find about them by open mouth, ie: Virtualbox, a free alternative to VMware from a work colleague (I used to work for the UK branch of Israeli-based NICE systems in 2007)

    Something that brings good free apps to the masses would be a boon.

  2. I think an independent app store, one that isn’t owned by The Big 3, is a great idea to maintain freedom. Imagine an app, let’s pretent a Wikileaks app, gets banned on the Big 3 platforms. That app could could theoretically still have a viable place on the independent app store.

    However, I don’t think we should continue with this silly “apps are free” model. It just doesn’t work. Apps take money and time to develop. Lots of both, really. You’re going to have to recoup that cost somewhere. In our Paint.NET example, you’re suggesting the old Slashdot advice: they still give it away free, but make money by selling documentation and training.

    Problem is, this hardly works for huge systems like Linux distros. For smaller, end-user apps like Paint.NET, this just doesn’t work.

    I propose an independent app store, perhaps owned by the Apache Foundation, but let apps be free or for cash, developer’s choice. Open source never was about “zero dollars”, anyways — it was, and is, about the source being opened.

    1. Well said, Judah, though I think you greatly overstate the consequences for Microsoft if the do nothing or if their app store is poor. I hardly think they would suffer the loss of a dime without a good app market, but I think they have a great opportunity to start making fractions from millions of sales from a well done curated market.

      Many of these issues are largely solved by Chrome/Mozilla’s. Store concepts, but both lack the power of integrated desktop apps. Many of these issues were resolved (on Linux) by good comprehensive package management systems, but these suffer from poor integration with commercial / for-purchase software. Hopefully someone will come up with a more comprehensive solution soon, but I don’t think there is enough pressure on Microsoft that their solution will improve much beyond basic user confusion.

      1. Judah, sure, I like free and open source software but I wouldn’t expect all software to be free this way, I think ideas to upsell books, training and support contracts alongside apps could work though. If the app could also, say deploy an app over lots of desktops in corporate environment automatically, this would be also nice for us IT admins.

  3. Those rogue download buttons probably are the only reason the application is still developed. There’s been a huge hole in Windows software monetization since the internet made Box Software largely irrelevant. The wild west of the web has created a situation where people will not pay for software except from a Big Vendor. I don’t blame them. There’s no real way to no what you’re getting and the ratio of good to garbage is entirely too low. Paint.NET is one of those very-good but not professional quality apps that should be priced around $4.99 but no one would pay for it with the non-existent payment methods that exist on the web. Hopefully Windows 8 will change that.

    Also, you can create a msi that has 0 clicks. Just double click on the msi file and it automatically installs in the default location and closes when finished. This is how I usually create them. The prevalence of bad featuritis installer is mostly due to legacy installer usage among developers who have been using them for many years. I’d be surprised if Windows 8 Metro allowed 3rd party installers at all. Should all go through the Marketplace like on WP.

    1. Agreed; those rogue install buttons are paying for the software.

      But really, this is Microsoft’s problem, too. The lack of an real marketplace for Windows apps has led to this situation where small developers can’t charge for their software: the developers would have to build their own online store, their own software update functionality, their own feedback system. And even if they did that, almost no one would buy the software, since people have grown accustomed to getting everything on the internet for free.

      What we’re seeing with Paint.NET (and indeed, Windows apps in general) is a symptom of the larger problem that only Microsoft can address for Windows apps: the real need for an app store with built in commercialization, software updates, feedback.

  4. I just went through this very (frustrating) process last night, with file de-dupe software. Thanks for showing how truly awful and time consuming it is.

    1. It’s not that we forgot about it, it’s that MS executed that poorly. MS didn’t give developers a compelling reason to publish via marketplace, and worse, didn’t give users a compelling reason to use it. End result: the whole thing failed, no body used it. It may have been one of those technologies that was ahead of its time, too early; failing by itself, but paving the way for other successful tech, like Apple’s app store.

      Win8 app store is an all or nothing proposal: the only way you get Metro apps is via the store. They’ve given devs a compelling reason to use the thing, and users are now accustomed to the idea. But we’ll see how well they execute.

  5. [sarcasm on]
    So it’s MS’ fault for not doing it properly first that these download sites have become mazes of malware land-mines? It’s not just greed and laziness on the part of the software developers partnering with them?

    2015: I really love my new [insert brand] ‘feature-PC’; the apps I get to choose from are awesome, and since there’s only one for each task (as decided by [brand]), I don’t have to make any choices, awesome!

    And all I have to do to keep my data alive is pay (each service) monthly to keep using it, what a deal! Much better than reading what’s in front of me, and practicing safe habits.

    Can [brand] tell me which possible mate is best too (so I don’t catch anything)? Or perhaps board up all those ‘dangerous’ areas of the city I might happen into, so that I can’t get to them without breaking some contractual agreement? That’ll keep me safe right? There’s some dangerous areas of my house too, perhaps they should come keep me out of those as well, and heck, why not let me pay them to do it?

    Internet = dead, long live Broadband+App Stores! 🙂

    1. Cause and effect. Microsoft didn’t give developers for their platform an easy way to monetize their software. End result: developers monetize their software via internet ads of the worst variety.

      Yes, that is Microsoft’s fault. They didn’t innovate fast enough when the internet era made box software irrelevant.

      And no, it’s not greedy to want to be paid for software that you developed, any more than it’s greedy to want to be paid for work you’ve done for your employer.

      1. Annoying, full-of-ads download sites existed before MS started the Marketplace.

        The thing is I want to choose who and where I get my software from.

        I’d rather shoot it out in the wild west than just accept what’s shoveled at me like it’s 1984.

        That’s why the Internet destroyed boxed software stores, people like choice, even if having it requires a little risk.

        When software is worth using and paying for, then I do. And funnily enough, all the quality software that I do use (freeware or otherwise) seems to come from legit web sites that offer direct, non-polluted download links.

        Personally I’d have given up on about 3 steps into that clown-barf, money-grab chain of clicks and ads, and just grabbed a copy of Gimp.

  6. Now compare this to the way you do it on a Kubuntu installation: start menu -> System -> KPackageKit, type in krita, ENTER, check the app in the search results, click apply, enter your password, ready.

    From the moment you decided to install the app to the moment you actually start using it you shouldn’t need a minute.

    Krita, for the ones not knowing, is sort of a equivalent developed for Linux, only better – check out its website. And of course it’s free.

    Now, two questions:
    1) Maybe the Canonical + partners repos could be the app market some commenters were talking about above?
    2) Anybody still wondering why I left Windows for Kubuntu about two years ago?

  7. I have used some strong words in this comment, it’s all meant to be constructive (not sarcasm). 8 )

    I’d like to see grandma even fire up a linux box, and make use of any of the apps including the browser.

    I get the bad web sites for free software. been there done that for many a free app. But going to a site that charges for software, well you just add it to a cart and pay for it. no ad link mines. so you have to be careful what you click on. like the sarcasm comment mentions. I’m a long time web app dever and love desktop apps and love making them. I HATE, let me repeat that I HATE web development. I have had nothing but problems and have yet to get a web page up and running. Mind you I have made a few web applications, but for me to get them to actually be served has been a huge fing nightmare. infact I’ve been at it now for a couple of years trying every now and again. both on win and lin based servers.

    I’m sure it’s just me cause there’s plenty of sites out there (can/should I include this one?), but damn, I’m not a stupid person, but this idea that ms wants to kill the desktop app, well good luck with that when the cloud goes down. and someday some hacker will take it down, won’t be me cause well I just don’t get web security. desktop app security no problem, IIS/web app pools arrrggggg!!!

    I also HATE the idea of having to get my apps served to me from some central controller. I started in computers during the days of mainframes and vt100 dumb terminals. that’s what people what to go back to? sure you got color instead of monochrome, you got music now instead of a beep, sure the cloud will be great for grandma to send her social security money to so the cloud can pay all her bills. if that’s what grandma wants then so be it. but it sure as he’ll is not what I want. I want my own pc with my own control (I guess that’s the real keyword here) and my own time to dev with or without the cloud or net.

    loved your blog by the way it was very funny.

    1. Hahah, thanks for the amusing comment, Mike.

      I would retort only that Microsoft does *not* want to kill the desktop app. It’s very much in their interest to make native Windows apps relevant again. That’s why in Windows 8, there will be a new special kind of Windows app, one that avoids the problems discussed in this post.

      It will be interesting to watch and see whether they can succeed.

  8. Oh and by the way how about these pop up browser windows with ads, doesn’t everybody not use a desktop app if there popup ads in them, yet for some stupid pitiful reason everyone puts up with them when their browser pops them up, why?

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