Windows Live Writer Team, I Feel For Ya

A few things I know about software installation in the software industry:

  • It’s the engineering job of last resort. First job you give to the new guy (or the college hire), first to outsource or offshore, first problems you’re happy to ignore (especially since during the development process you don’t see it). (I’m sure there are exceptions to this, but it’s a good start.)
  • The Internet made it easy to bundle/upsell/force things ya don’t want. Real, we’re talking to you.

So what happens when you’re building a very cool app and you get whomped with these two things?

Ladies and gentlemen, the Windows Live Writer setup process.

WLW is a desktop blogging tool, one of the best in the biz, easy to use, smart in an Intellisense sort of way (does very good things with images in tables), free to everyone and compatible with Blogger, WordPress, Microsoft MSN Yahoo Something Live Spaces, etc. It’s one of the few Microsoft software products you can use where it really feels like the people working on it put their soul into it, and the love has been shared back. I’ve been using it for months. (The WLW blog hasn’t been updated for 2+ months, which is not a good sign.)

Anyway, I was using a beta version which had expired and I kept getting a nag dialog, and then I hit a bug only solved by an upgrade when posting on the WhitePages Developer Blog, so I finally tried to upgrade.

Time spent upgrading from beta to final version: 3 hours. (That includes about 45 minutes downloading and evaluating alternative tools like Zoundry when the WLW installation was too painful – but I didn’t like those tools enough to continue.)

Some of the highlights:

  1. That initial nag dialog had a “download” button, but it didn’t actually download the client. It instead took you to the WLW website, where you then searched about for a downloadable client. This made sense in the few years after the web was ubiquitous and before automated installers were ubiquitous, but those years passed some time ago.
  2. Download and start the installation, and immediately comes an inscrutable dialog (unfortunately I didn’t know I would be writing a blog post or I would have captured it), saying that you can’t continue until you install “Windows Update Agent 5.8.02469.”I have no idea what this is, or why I would need it. There are no buttons on the dialog to install it, or explain it, or point you to a website explaining it. You close the dialog and then… you’re stuck.
  3. I figured that this might be connected to Windows Update, so I tried to start Windows Update. Then I entered some crazy circle of hell where I went to, it kept warning me that I was going to install unsafe software, I kept installing the same ActiveX control over and over again, but nothing ever, well, happened. So I tried rebooting.
  4. I restarted the Windows Update website, and then it started to spin while investigating my computer. So I googled “Windows Update Agent 5.8.02469” and found one technical post surrounded by spam on all sides. The instructions are slightly off but it pointed me to a directly-downloadable exe, so if you see my post when searching, follow step 3 from that link.
  5. That download and install didn’t actually work, but it did tell me that something was already installed, so I figured I’d try WLW again.
  6. Now this mysterious dialog is gone and the installation continues.
  7. The installation asks me the standard “do you want to install Microsoft X, Y, & Z,” and I say no. Then something I’ve never seen before happens – the installer decides to search my computer to find if I have other things on it, so it can upsell me another set of applications if I don’t.Here’s the dialog:


    The first version of this dialog told me it was searching my computer for other products I’d like to install. Then I got the “sorry” version.

    It’s one thing to upsell me. It’s another thing to force me to wait so you can decide what to upsell me. It’s yet another thing to force me to continue to wait because your installer is failing so you can decide what to upsell me. (A good rule of thumb: if a process between your software’s definition of end state and the customer’s goal is failing and you can complete the customer’s goal in any way, shut down the process.)

    I was stuck on this dialog for ~15 mins.

    Another reason this is a weird dialog is that the only thing I can do is Cancel the whole thing: if you don’t see the “Waiting,” you don’t realize that there are multiple things going on at one time, and Cancel stops all of them, not just the one you don’t want.

    Oh, and “Sign-In Assistant”? I still have no idea what that is.

Finally the pain ends, the dialog allows me to start WLW, and I’m able to publish a blog post with some images. You can see how Steps 1-6 come because the setup team just doesn’t really know how to do this right, and Step 7 comes because the installer doesn’t care about me, it cares about its other software.

I don’t know anybody on the WLW team. Perhaps this unclear, convoluted, prone-to-fail introduction to their product was their goal.

I doubt it, though. I assume that they, like me, are victims – of company priorities and of setup software sold out to the lowest bidder. They worked hard on building a great app, and then they got surrounded by things out of their control. Maybe they didn’t see it coming – this installation process didn’t exist in the earlier betas, maybe it was a late bolt-on. Maybe it wasn’t tested. I don’t know – all I know is the results, which say that at the very least, upgrading from the beta is too hard for normal humans.

Installation is important, especially when it’s hard. One reason given for Majestic’s failure in 2001 was that only 8% of the people who started the install were able to complete it. (The number’s from memory, I don’t remember the source.) Google Talk never really got credit for their brilliant initial install – click the download button, say OK, and you’re done – it just started, not another dialog. (A few reviews mentioned it at the time, here’s the only one I can find now. I don’t know if it still works this way.)

This version of WLW is better, it’s fixed a few annoyances I had, and I’ll keep using it. I hope that band is still together or gets back together, it’s a neat product. Here’s hoping they get to make the whole experience better for their users.


4 Responses to “Windows Live Writer Team, I Feel For Ya”

  1. Joe Cheng [MSFT] Says:

    Sigh. The real story is not quite that simple, though no less frustrating. The good news is that smart people are working hard to make sure the Windows Live installer gets fixed for the next release.

    And the Writer team is alive and well–no need to worry about that!

  2. Mike Tremoulet Says:

    Okay, so catch me up here. You’re the first person I know (IRL, anyway) using WLW. What does it offer you? I’ve only ever used the admin interface of Blogger/MT/Wordpress over the life of my blog, and recently started using Qumana on the Mac to author posts offline. However, I don’t know that the offline client adds anything to the process for me.

    I’ve seen a lot of love for WLW written online. What’s the part for you that makes it so attractive – enough for me to put effort into switching?

  3. Scott Ruthfield Says:

    Thanks for commenting, Joe. The situation is always more complicated, isn’t it?. 🙂

    I’m sure people would love to hear more about the making of the sausage, even if members of the team feel like they need to comment anonymously.

    Thanks for the pointer to your blog as well!

  4. Scott Ruthfield Says:

    Hi Mike –

    I use WLW for a few reasons:

    1) Practical: I really do write blog posts offline. I wrote the latest WhitePages Developer Blog post on an airplane; I sometimes write on the bus. Making time to write when I’m away from the noise often helps.

    2) Visibility: I’m more likely to write (or jot down the beginning of a post) if my window for writing is always-visible. A desktop app means it’s in my taskbar, I don’t have to open up a WordPress window, and it just _feels_ like a better place for drafting work. I’d rather use the WLW list of drafts than the WordPress manage tab.

    3) Confidence: I’ve had enough text boxes go bad that I trust a desktop app much more than a web app to auto-save drafts, not crash during usage, not lose content when I accidentally hit the back button or key combo (as I’ve done already in this session), etc. Since I have to force-close Firefox every day or two after my 30 tabs take up all available memory on the machine (and the machines nearby), all the better to be independent of the browser.

    4) Functionality: I like smart editors, and none of the online blog editors are there yet (if they will ever be). Using WLW, if you add a table and then put an image in that table, it automatically resizes the image to fit the table, creates a thumbnail and links to it, keeps the sizes standard, etc. A fancy textbox is just not going to do that. Simpler things like creating hyperlinks inside text are just easier and faster.

    Sometimes I end up in the WordPress UI anyway, and it’s certainly not bad, but overall I prefer writing in WLW. (I do all my blogging from a Windows laptop – there seem to be some great clients for Macs, I haven’t checked them out yet, maybe in a few months.)

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