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Windows Last Stand

I have an ancient box with Windows XP as its only operating system gathering cobwebs in a space under my desk, right where it was the last time I used it. That was back in April of last year, on the day that Microsoft quit supporting XP. Up until then, it’d been used mainly to process credit card orders from an online store I manage. The bank’s required software for processing won’t run on anything but Windows, so I kept it around for that purpose.

Windows XP
A look at Windows systems use on my old machine, first as Firefox is loaded, then as Thunderbird loads. This is after AV had finished updating.
When I took it out of commission, I decided I was through with Windows for good. No more dual booting. No more keeping a Windows machine running all day just to process plastic. No more blue screens. No more rebooting for no apparent reason except that’s what Windows wants.

I cancelled my deal with the bank, switched the site to taking PayPal only and shut down the box for good.

Until today, that is.

It’s tax time and I do my own taxes using tax preparation software. The trouble is, no decent tax software runs on Linux. I considered doing them in the cloud, but I despise doing anything in the cloud. Not only that, I also do the taxes for a few family members, and all of the online tax sites want you to pay again and again and again when you prepare multiple returns — once for each return you do.

So today I pulled the cables from my main Linux desktop, plugged them into the Windows machine and hit the power button, just to see if it would still boot for a few days — long enough for me to prepare a couple of returns. Because the machine is old and hadn’t been started for a year, I fully expected the hard drive to fail during boot. Unfortunately, it booted, and in a few minutes I was greeted by the Windows splash screen.

I say “unfortunately,” because I’d forgotten what a pain in the kiester running Windows can be.

Right after boot, I was notified that there were important “updates” that needed to be installed. That turned out to be Adobe Reader, of course, and since I figured I wasn’t going to need to look at any PDF files to do my taxes, I took a pass on the update. Then AVG reminded me that it might be a good idea to update the antivirus system. I almost took a pass on that too as I was only going to be online long enough to purchase and download a couple of apps.

I quickly came to my senses and changed my mind, however. After all, I was in the world of Windows, the most insecure operating system on the planet. Not only that, I was using a version of Windows that hasn’t been supported for the past year. As I was planning to type some payment info on the keyboard, data I’d rather not see in the hand’s of some Russian cracker hacker, I decided to play it safe. I hit the button and told AVG to go ahead and update.

When I saw that the update was going to take over an hour I almost changed my mind and cancelled out. Then I thought (always dangerous), I could go ahead and get started while AVG was updating. After all, Windows is capable of multitasking. I clicked on Firefox to get started on the task at hand.

I’d forgotten that antivirus software hogs resources. With AV updating, Firefox took forever to load, and even after it did, it was barely responsive. But I was eventually able to get to the tax software folks’ webpage and navigate to check system requirements — just to make sure XP was still supported — and to purchase the software.

Then I couldn’t remember my login information from previous years’ purchases, which would be safely stored in an email somewhere — so I opened up Thunderbird for a look-see.

With AVG, Firefox and Windows already maxing out resources on my old metal, T-bird took a couple of eternities to load — first giving me a blank white screen for ages. When it finally opened, I used Thunderbird’s quick filtering feature and quickly found the email from seven or eight years ago with the my account number. Then, or course, I couldn’t remember the password, so I clicked for a password reset and returned to the email client to grab the link from the email I’d be sent.

About as soon as I got the password changed and was ready to place my order, Firefox and Thunderbird both ran out of resources and refused to respond or close, necessitating the opening of Process Hacker, the third party software I used as a task manager in Windows. After three minutes or so, Process Hacker finally found the resources to open and I was able to kill Firefox and Thunderbird.

At this point I decided to make a pot of coffee and wait for AVG to quit doing its thing before continuing — which took another forty five minutes or so.

When the AV program finally finished, Firefox was much more responsive. I went back to the tax company’s website, discovered my shopping cart had emptied when the browser crashed, and went through the process again. When I was finally through with the purchase, I downloaded both the federal and state programs into my downloads directory.

This being Windows, I then clicked Start and Run, then navigated to the install file for the federal tax program. I clicked to select it, then clicked “OK” in the Run box.

Of course, I was met by an error.

“The file is not a Win32 file.”

What? This tax company doesn’t even port to Mac and they damn well don’t port to Linux. What other kind of file could it be? Kaypro, perhaps? I repeated the step, this time trying the state version.

“Sorry. Installer can’t find a federal version installed on this machine. Federal version must be installed before installation can continue.”

At least it was evidently a Win32 file.

Figuring I probably had a broken download, I went back to the good tax preparers’ website and downloaded to the same location, clicking through do-you-know-this-file-already-exists and agreeing to an overwrite.

“Error. We can’t save file because we don’t know what kind of file it is. Contact the vendor or choose from list.”

I tried it again, with the same results, so I downloaded to the desktop, which was successful. But again Start>Run>navigate to desktop version yields: “Not a Win32 file.”

I was ready to look for a help desk number for the tax software people, but at the last minute thought I’d try one more thing. I opened Windows Explorer, Redmond’s sorry excuse of a file manager, found the file and clicked on it. Voila! Like magic, the program began installing.

So now I seem to be good to go. I’m just wasting my time writing this article because I hate doing taxes.

I know what you’re thinking.

You’re thinking that my problem is with old, antiquated hardware and has little to do with the operating system. The hardware is obsolete, true enough. But I have a laptop with similar specs running Bodhi Linux and guess what? It runs just fine. It even runs Netflix — like a charm.

I hate Windows — and today has reminded me why. I’m determined not to go through this again next year.

After I finish this years taxes and get them printed and in the mail, I’m going to save the resulting return files on one of my Linux machines. Then I’ll partition the hard drive on this old machine and install a reasonably lightweight Linux distro, probably Bodhi Legacy. Then I’m going to try my old WINE shortcut trick and have WINE access the tax software from the XP FAT 32 partition to see if it runs. If it works, I’ll be good to go when next year’s tax software’s released. I’ll just download the new software from Linux onto the Windows file system and install it from WINE.

If that doesn’t work, I’ll have a year to work on it and figure out what it’ll take to get it to work on WINE — find all the .dll’s and all that. If even that doesn’t work, I’ll breakdown and do my damn taxes online. That, or use a pencil and slide rule.

As I said, I’m through with Windows for good. Except at my “day job” — but that a whole ‘nother story.


  1. Mike Mike April 6, 2015

    The irony is that by the time you did all that, you could have finished your taxes on paper and been done.

    Seriously though, don’t support companies like Intuit (makers of TurboTax and Quicken). They are almost single-handedly responsbile for the lack of online free-to-file federal tax forms in the U.S. They’re extensive lobbying efforts have stalled any such progresss in the name of “protecting” the populace from “confusion” and government overreach.

  2. Mike Mike April 6, 2015

    Argh…I meant “Their”, not “They’re”.

  3. Colonel Panik Colonel Panik April 6, 2015

    FOSS if it is good enough for your computer it is
    good enough for the other parts of your life.

    Open Source Everything! Everything!

    Yeah, I know that becomes inconvenient sometimes
    but it will put control back in the hands of the

  4. Uncle Ed Uncle Ed April 6, 2015

    Christine, you went through EXACTLY what I did when I got started on my taxing. Well, except that I bought my last laptop with W7 a few years back when I was teaching and had to be able to run that other office program at home. It dual boots and defaults to Linux, of course, but W7 is available if I have to have it.

    As in your case, it had been almost a year since it had been up and running in W. After it was kind of cooperating, I decided that next time I wake it from long nap, I’ll get logged in and then go get a cup of coffee–in another town.

    FWIW, and I am terribly ashamed, I’m running Quicken 2003 in WINE on Mint 17.1. It has given up trying to get me to update, so it lets me just use it. It isn’t cluttered up with all the investment and stock market following stuff that the newer versions do and does my checkbook just fine.

    I’ll probably try the tax software in WINE next year and if it works, you may hear the “YES!” all the way from Arkansas. OTOH, there may not be one; Linux does what it does so conveniently that I rarely have to work hard enough to justify shouting.

    Hope you and your family came out okay with your taxes. We and my daughter’s family were fortunate to end up fairly close to even, which was nice.

  5. Phil Phil April 6, 2015

    I had a similar experience and ended up using Taxact on my Windows box. At least the Federal is free if you avoid the continued hounding to upgrade to the premium version.

    Agree with Mike, Intuit is evil for what they have done with tax filing software.

  6. John S John S April 6, 2015

    In order to do taxes this year I had to create a login on my wife’s Windows 8 laptop. And interesting experience to say the least. The laptop has specs that are four-times faster than my 10-year-old Linux PC. And the open-source apps that I run in Linux run like stink on the laptop. But the OS is slow… circa Win286 from 1987 slow. I suspect no 8-core processor on Earth could wake up that POS OS.

  7. Hunkah Hunkah April 6, 2015

    I made that decision a while ago. I was doing something 8 years ago on Windows and it was stuttering and chirping a music video I was trying to listen to and write a paper… then boom! Crashed. Lost my paper. I said that’s it. Frig this. I switched to Fedora. I used to have a few programs that I missed at first, now… I don’t even remember what they were. I do my taxes online. I don’t care. It’s cheap and easy and runs in a browser.

  8. Bob Bob April 6, 2015

    For this, and other similar reasons, I keep VirtualBox on my main linux machine. Works great (well, as great as windows will ever work).

  9. wh7qq wh7qq April 6, 2015

    XP is the last W$ OS I will ever buy. Forced to buy it when Redmond decided that ’98 and all the hardware that ran it were obsolete and I had a useless laptop and had to replace the mobo, cpu, memory and graphics card on my box to run XP. I bit the bullet but then downloaded a copy of Red Hat and progressed through Fed, Knop, Kano, etc. to Mint of late. Still have that ancient laptop running AntiX and supporting a USB microscope at my soldering station.
    I took my security in my hands and ran free TT off the web last week. It ran well and got all the refund it could for me. A few years back I tried TaxAct and did not like it. I used to have to spoof TT to get it to run on Linux/FF but even that has gone away.
    I do keep an XP hd on one of my boxes but it is disconnected…not a dual boot. I have yet to find a Linux sub for the SD Assn’s SD and USB formatting utility…sometimes nothing else seems to work as well.
    My neighbor talks about the huge .iso and update files for W$ 10 and I just shake my head. He buys laptops

  10. tracyanne tracyanne April 6, 2015

    I haven’t used Windows since I retired. The only thing I really miss is a good Graphical web design tool like Dreamweaver, or even Visual Studio, since I like to keep my hand in. I had hoped Monodevelop might have one by now but unfortunately not.

  11. Dot Net Dot Net April 6, 2015

    I had similar problems running tax prep software. I seem to remember that TaxAct worked OK-ish in Wine. There were problems with .net compatibility, I think… and fonts… and other things… So, I gave up – and do them on-line.

    My thoughts:

    The Government should provide an open source tax prep software program. They wrote the rules, they should be able to parse those rules for the paying citizens – so we can continue to pay for gov to exist.

  12. Rudi Pittman Rudi Pittman April 6, 2015

    How long would it have taken if you installed a fresh copy of XP using the same key from your old system into Virtualbox on your main desktop and then did your taxes there?

  13. Me Me April 6, 2015

    Here’s how I solved this problem for myself: I gather all the tax year’s forms that I typically use (Federal and state), re-create them manually in a single LibreOffice Calc file, one per tab, and make them self-populate and self-calculate as I enter my data. Then I save .pdf copies of all the forms from and my state’s tax site, enter my calculated data into them, print them, and mail them. What are those commercial tax programs anyway except self-calculating spreadsheets, cleverly disguised inside question-and-answer skins? And if the IRS and state want me to e-file for their convenience, they can bloody well provide e-file capability to EVERY taxpayer FREE of charge. Why should people have to pay in order to comply with tax law?

  14. Dot Net Dot Net April 6, 2015


    1040EZ or bust.

    There are several problems doing the good ‘ol pen/paper method in today’s tax world. It’s possible, in fact maybe likely, that there’s a ‘checkbox’ that if you find it – you win an extra 10% on your return… or — if you fail to find it, you owe an extra 10% above what you’ve already paid.

    While I agree with you in principle, generally the rules are complicated and far too difficult to apply effectively anymore on your own.

    Why should people pay to file? They shouldn’t — gov should already have everything done and filled in, they have the info already on file… tax payers should be able to just sign the filled in forms or update with lottery winnings and then sign.

  15. Geoff Geoff April 6, 2015

    Have used Tax Act Online for several years (federal is free) . . only pay a minimal amount for filing the State returns.

    Really no issues with Tax Act – – seems able and fast from simple to complex returns, including error and issues checking.

    Anyway, works for me and a couple million other folks.

  16. Duncan Duncan April 7, 2015

    I dumped MS when they took eXPrivacy one too far and decided I had to check in with MS for permission to run my validly purchased software. No such anti-feature was going to hit MY system, full-stop. And it didn’t. If Linux hadn’t been around, ironically given the supposed purpose and the fact I had never even /considered/ pirating MS before, I’d have had to start pirating the software in ordered to run it. Luckily for me, Linux was around. =:^)

    Based on that, reading (as a hobbiest developer that had previously considered freeing my own sources, but that was before I knew of the GPL) Eric S Raymond’s The Cathedral and the Bazaar and *VERY* much identifying with it, and the bad experience I had with nVidia’s servantware drivers, I very quickly eradicated servantware from my computer! If I wanted servantware, I could have very well stayed on the MS I had worked with for a decade and thus was familiar with; I switched to Linux for a *REASON*, and that reason was *NOT* to run servantware!

    So it has all been freedomware for some time, here. Not as much as a servantware driver or flash player (with one exception, the 1993 vintage Master of Orion for DOS, which I still play, in freedomware DOSBox of course).

    Meanwhile, taxes… Actually, I never bought tax software on MS, either. I did them on paper back then. I do them online now, and either the laws have changed or I was missing something previously, because the last 2-3 years I’ve actually gotten more back than I expected and was getting before (I deliberately have federal witholding setup so I should actually owe a bit at tax time; this year, most of the federal refund was due to my being eligible for higher obamacare subsidies than I actually took, tho before that was figured in I owed something like $6, still better than the $100 or so I expected to owe).

    And as it happens, I’ve been eligible for free federal for awhile. This year, they (Intuit/TurboTax) even did free state, at least for my state (AZ). I was actually considering doing them online and comparing what I got doing them on paper, then sending in the paper version for state, if I had to pay for it this year, but since it was free too, I just let it handle things.

    Meanwhile, for the first time this year, I actually got taxes done in mid February, basically as soon as I got a bit of time after getting the w-2s, instead of waiting until the last minute! =:^)

    But I still wish we could just go to and do them online, like most not-third-world nations do, these days. Well at least they don’t require that and only accept servantware browsers (IE/Chrome/Safari), like some nations apparently do. At least the variety of private tax preparers provide a variety of online solutions, too, including some that work very well indeed with freedomware browsers like firefox, even with reasonably tight privacy-by-default extensions and policies! =:^)

  17. Sylvester Sylvester April 7, 2015

    You can always use LibreOffice Calc to do the taxes. I’ve been doing that for years.

    Last time I used Windows XP was 4 years ago when there was a game I played that just won’t run in wine, but that had been resolved. All my Windows games now run in wine, except for a handful that don’t run, but they are all old games that won’t run in new Windows anyway. I’m also buying Linux games, so no more Windows games to tackle.

  18. archuser archuser April 7, 2015

    Linux may be good for casual home user, but if you want to login to your company network or do something that is designed for say windows only , you are stuck , i realized the same and gave up Linux for good.

  19. enkil enkil April 7, 2015

    Why do you hate MSFT , did they do something to you, did they kick you out of your job , i think your enemity with MSFT is personal , it has nothing to do with Windows , which is a fine OS by the way, majority of the users in the world use windows and are fine with it.

  20. ninmah ninmah April 7, 2015

    Hi Christine,

    Please suggest a distro, DE in Linux to get the best linux experience, i have tried a couple of distros and my experience has been less than ideal,for me Windows is indispensable as i believe linux still needs a lot fo work on all fronts be it apps, drivers, eco system as a whole.

  21. Albin Albin April 7, 2015

    You’d have done a whole lot better to partition a decent machine’s hard drive and installed Windows 10 Technical Preview on it long enough to install the tax software do the taxes. Then erase it if you like.

  22. frex frex April 7, 2015

    Duncan, its “hobbyist”, not “hobbiest”.

  23. Brandon Brandon April 7, 2015

    @ninmah – “Please suggest a distro, DE in Linux to get the best linux experience, i have tried a couple of distros and my experience has been less than ideal,for me Windows is indispensable as i believe linux still needs a lot fo work on all fronts be it apps, drivers, eco system as a whole.”

    I would recommend Pinguy OS or Linux Mint.
    ( – ( For a list of Distros though you can look through

  24. Jono Jono April 8, 2015

    Sad reading the comments of the MS fanboy club – they clearly have never tried Linux or are paid by __? (shh).
    I can recommend Linux Mint, have been running it for about 5 years now.

  25. Rocky Rocky April 8, 2015

    I retired my old XP-machine last year, but before I repurposed the hardware I got Dish2VHD from Microsoft Technet and now I’m running the XP in a virtual machine for those times I need to run some old application.

    You can find Disk2Vhd at Technet here:

  26. ipcamper ipcamper April 8, 2015

    Unless you have a really complex tax situation, download the forms from All of the tax forms at are PDF files. Open a good PDF editor, enter the data, save a copy, and print it out. A simple calculator is all you need. Snailmail works fine, and it is far cheaper than than online filing, or buying software to do it.

  27. Richard Thornton Richard Thornton April 8, 2015

    So what? You don’t like windows? Don’t use it.
    These types of OS stories
    Are boring and stupid.

  28. Jack Halem Jack Halem April 8, 2015

    In 2012, I began my long quest to learn GNU Cash. While it took almost a year to become fully competent – it was well worth the reward. December 2013, was the last time I used Widows for anything. I have been operating my business 100% Linux since January 01, 2014.

  29. Mike Mike April 8, 2015

    @Richard Thornton

    So what? You don’t like the story? Don’t read it.
    These types of comments are boring and stupid.

  30. Ostips Ostips April 8, 2015

    Windows feels alien to me these days. The days of wondering how I could live without certain software has gone, the biggest one being Dreamweaver because I now use Geany. I have one confession to make, I still use photoshop 7 in Wine, just can’t get on with Gimp.

  31. Richard Thornton Richard Thornton April 8, 2015

    To me, it’s a ” yet another Linux user, who thinks he’s smarter than all Windows users. Use what you like,
    Why the need to brag?

  32. ScottyK ScottyK April 8, 2015

    Why are you even messing with the actual windows machine? Just load up a virtual machine of Windows on your Linux box and press on. VirtualBox or Vmware (what I prefer) allow you to run computers within computers. I have a windows 7 VM that I use to prepare taxes, and play the occasional game of Grand Theft Auto Vice City.

  33. Richard Thornton Richard Thornton April 8, 2015

    Finally, a smart comment.
    I have several Windows boxes with VMware 11 running many open OS’ s such as OpenBSD, FreeBSD, and OpenSUSE. My Ubuntu box has a valid 64 bit Windows VM.
    I like having full use of my systems 100% of the time.

  34. Jack Jack April 8, 2015

    You got it correct. Linux users are smarter than windows users. In fact Google removed all Microsoft computers from their home office over 5 years ago. FYI, Android is based upon Linux. Even Bill Gates now uses Linux – that must say something.

  35. Greg P Greg P April 8, 2015

    Aside from using Win7 on a VirtualBox VM on my Linux computer for taxes, the other thing I do after finishing is to send the PDFs as well as the tax files to my Linux part of the drive using an SSH client (sftp) over my home network. This is the most convenient way to transfer the files.

    Part of the reason for doing this is a basic worry that my Win7 may not continue to work forever.

  36. DaveJ DaveJ April 9, 2015

    Like you, I recently had to fire up an old Windows XP desktop to try and access an SD card that contained data from a medical device only supported by Windows or Mac software. And even though the laptop is decently powered even for XP, with 2GHz CPU and 2GB of ram, my experience was identical to yours, including the need to update the anti-virus software. Unlike you, my need to access this data will be an ongoing event, so there is NO WAY I am going to put myself through this kind of agony on a routine basis.
    Fortunately I was able to work out a way to successfully run the Windows software in a virtual XP machine with Virtualbox on my LINUX Mint desktop. And once I figured out how to get the virtual XP machine to read the SD card from the medical device, my problems were solved. No more need to go through the agony of a true “Windows Experience” again because the medical equipment corporation that makes my device thinks that LINUX users don’t rate software that works on their computers, even though the similarity to LINUX and the BSD-based Mac computers that they DO support means that it would only require minimal effort/expense on their part.
    Thanks for sharing your experiences, it’s good to hear someone else besides me feels the same way I do!

  37. jelabarre jelabarre April 10, 2015

    TaxACT **used** to work under Wine. Ever since some update around 1.7.18 (I think) it no longer works. I had meant to follow up on that last year, but other things pushed that out of my mind. Since I had already been running the Win10 TP on a scrap laptop here (battery & dvd drive are shot) I ended up using that this year (along with putting whyTunes on it to make use of an itunes gift card I got) for my tax filing. Next year I’ll probably try TaxCut or some other product instead, and TaxAct can stuff their broken software (shoddy design and interface, entirely unrelated to the platform it ran on).

    It’s time for ALL Linux users to demand software vendors at least *validate* and fix their software under Wine, if they aren’t planning on making Linux ports.

  38. Jack H. Jack H. April 10, 2015

    I know I commented before. Regarding Tax preparation using Linux. I highly recommend GNU Cash. It may take a little time to learn how to use it properly. Put the GNU Cash file into a separate folder. GNU Cash saves previous files in the same folder. That way you can always to back to a previous file. Since GNU Cash offers all kinds of reports, one can make any kind of tax report needed. Plus your accountant can install GNU Cash for free. Me, if concerned, I take a laptop with me to the accountant, and can give them anything they want. Take a usb stick with you and you can have your tax person print out any report you generate.

    I was using Quickbooks before it was released for sale over 20 years ago. I was a pre-release user. My migration to GNU Cash was somewhat painful – but the rewards were worth the effort.

  39. Greg P Greg P April 10, 2015

    Response to Jack H:
    I stopped having an accountant do my taxes when I realized that what he was having me do was all the grunt work of collecting the information on forms, then taking those forms and plugging the information into tax software, charging me multiples of what the software cost.
    I cut out the middle man and save money every year.

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