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It’s Windows Time in Linux Land Again

Using Windows. What a horrible thing to ask a Linux user to do.

Linux Tux smashing Windows

Every year at this time I have to scramble to boot into a Windows partition to do my taxes. I could do them online, safe and secure in my Linux comfort zone, but I do taxes for three people and all the online services want to charge extra for each and every return. If I download and install the software onto my own machine, there’s no extra charge. Trouble is, none of the big three tax programs supports Linux. Tax Act, the cheapo bottom of the barrel one that I use, doesn’t even support Mac.This means that every April I get a reminder of what a pain Windows can be.

This year I decided not to trust Windows to handle the financial end when purchasing this year’s tax program — Windows security being what it is — so I took care of that in Linux. In the process, I discovered that Tax Act has added a new wrinkle. Every time you try to access your account on a new machine, you have to wait for an access code, which is sent to you by email.

Other than that, it was smooth sailing….

Well, not really. Lots went wrong, starting with sticker shock.

Because I run a business, however small, I can’t be a bottom feeder and use the federal-is-free-but-you-pay-for-state version. Nor can I use the next tier, designed for the homeowner who has to deal with investments, interest and the like. I have to go all all the way up to Premium, which is where they keep the Schedule Cs and inventory counting routines squirreled away. The price for this has been on a steady uptick for the past decade or so, from about $30 to $50 last year. This year the price jumped to 85 bucks. For a second, I considered just forgetting it and doing my taxes the old fashioned way, but I couldn’t remember where I stored my abacus and went ahead and let loose with the money.

I better get a hefty refund on my taxes, I thought. At least enough to pay for this.

My original plan was to keep my trusted desktop running Linux and use it for finding all the numbers I’d need to plug-in to Tax Act for it to do its thing with them. I’d just purchased the desktop in December, a refurbished machine that had come with Windows 10 preinstalled, which I kept on a small partition, just in case, when I installed Linux Mint on most of the 2 TB drive. But I figured I’d let it stay in Linux, where it belonged, and install Tax Act on a Windows 7 partition I have on a System 76 laptop.

Windows on a System 76 machine? Sacrilege, right? Don’t blame me, I didn’t do it, even if I was partially responsible. When the used machine had been gifted to me, it had come equipped with Windows installed and nothing else. I fixed that. These days, the majority of the hard drive is devoted to Linux, with a tiny little corner reserved for the Windows it came to me with — again, just in case. It’s what I used for my taxes last year.

Windows being Windows, a monkey wrench was thrown into the machinery right off. I booted the laptop into Windows, which then refused to connect with the Wi-Fi. It found the on-board Broadcom Wi-Fi just fine, but every time I’d try to get it to connect, it’d throw up an “unknown error” notice and ask if I’d like to enable logging so I could figure it out myself. This was odd, considering I’d used the machine to do my taxes last year, and it connects with the Wi-Fi just fine in Linux. But I wasn’t going to spend the better part of a day trying to fix it — I had no desire to start relearning my way around Windows. Time for Plan B, which was the reverse of Plan A: boot the desktop to Windows and use the laptop in Linux for finding all my facts and figures.

So, I booted the desktop into Windows 10. Again, with Windows being Windows — and me being me — I hit another snag right away. It turns out that the Windows install on the desktop had been a brand new OEM version. My grace period had expired and Microsoft would very much like for me to add my registration key. Fark. I had (and have) absolutely no idea where it is. I remember seeing it in the box when the computer had arrived from Amazon, but since I was going to be installing Linux on it, I didn’t pay it much mind — you know, proprietary Windows crap, right? Knowing me, I probably threw it out when I disposed of the box.

Windows offered an option to “do it later,” which I clicked. I was informed that some update features would be disabled, but I was granted access to Windows, although with click through notices telling me that I was using a “counterfeit” version of Windows occasionally popping up.

As usual, I did my roommate’s taxes first, because hers are the easiest. I’d already made a thumb drive copy of her Tax Act file from last year, which Tax Act uses to import last year’s info into the new return, meaning there’s a whole lot of fields I don’t need to fill out. When I got to the part that asked if she’d used Tax Act last year and would I like to import that info now, I clicked “Yup” and plugged in the thumb drive to copy the file.

Trouble is, Windows didn’t see the thumb drive and no amount of coaxing could make it do so.

I didn’t mess around with that long. I did a quick search and found something about USB ports having to be activated in Windows, which I thought odd because I’ve never had to do anything to get USB ports to work in hard-to-use Linux. I wasn’t going to spend any time trying to figure that out, since there was an easy work around. I rebooted the machine into hard-to-use Linux, opened a file manager, copied the needed file into the proper location in the Windows partition and rebooted the machine into Windows.

From there, doing my roommates taxes was a breeze — until it came time to print her return.

Like me, roommate always files a paper return. None of that online filing stuff for us. Call us old fashioned. We are, and there’s a good reason for that. We’re old.

I hit print and nothing happened. I checked to make sure I had the printer turned on. Yep, there was a green light. I hit print again with the same result. Then again and again and again. Eventually I realized that continuing to click “print” wasn’t the answer.

Tt turned out to be another configureatin problem. That, and no driver. Windows wasn’t configured for this printer and was trying to print to something called OneNote, whatever the hell that is (don’t tell me, I don’t really want to know). I did some futzing around and discovered that Windows saw the printer just fine, but couldn’t use it because it didn’t have a driver for it. I looked through Window’s list of readily available drivers, and discovered that the Deskjet 1000 I use (a horrible printer, BTW), evidently doesn’t exist in my copy of Windows’ world. I found a screen that asked if I’d like Windows to find the driver online. I clicked “make it so.”

“Dave, I can’t do that. You have’t entered a registration key and I might be counterfeit.”


The good news was that Hal did discover that my USB ports weren’t activated and fixed that for me.

I found the “I have a disc” option and looked around for the Windows install disc that had come with the printer when I bought it a year-and-a-half ago, to no avail. Next week, as they say, I have to get organized.

This was a problem. I wouldn’t be able to print the return from Linux, as the Tax Act program is necessary to bring up the proper forms and populate them. Actually, there’s probably a way, but I wasn’t going to spend a day figuring it out.

I came up with another cockamamie solution, however. Since I had printed returns on this printer from the System 76 machine running Windows last year, I figured I could boot it into Windows, copy in the “install.exe” files from the desktop to use to install Tax Act on the System 76 laptop that couldn’t connect to the Internet in Windows, and print from there.

Confused yet? Good.

Then, while booting the laptop, I had an aha moment when my memory cells began to work for a couple of seconds. Last year, I remembered, I’d also had trouble getting the laptop to connect to Wi-Fi in Windows and had fixed the problem by using one of those little Wi-Fi dongles. I looked around for the wooden cigar box I use to keep things like dongles and spare thumb drives, found a dongle and plugged it in. It worked. All that was left was to find my Wi-Fi and tell Windows to connect.

Long story short: Thanks to Hal, Windows 10 on the desktop now had working USB ports, so I was able to easily transfer my roommates file to the Tax Act installation on the laptop. I plugged the printer into the laptop, told Tax Act to print the return and it was done. But jeez, what a headache this ordeal had been.

I’ll begin preparing my taxes shortly. Hopefully not, but there might be a Part Two to this story.


  1. tracyanne tracyanne April 17, 2017

    Don’t know if any of this will help

    I did a search for “US Taxes with GNUCash”

    Question, will Windows allow you to “Print to file” and thereby create a PDF (or do you need a special 3rd party install for that), which you can later use on a different OS, Linux, to print the tax return.

    I use that feature all the time, as I don’t carry a printer around in our Motor Home.

  2. Mike Mike April 17, 2017


    That’s a LOT of hassle dealing with all of Windows’ BS just to file taxes.

    I just use the Free File Fillable Forms online..boom, done. Sure, you have to know how to do your taxes, but are they really that hard? My state offers online forms too.

    I’ll bet I finished faster than you did, and I did it all from Linux, with no commercial tax software at all.

    F’ Windows and commercial tax software.

  3. Autumn Autumn April 17, 2017

    I’ve used eSmart Tax and its predecessor, whose name I can’t remember off-hand, for about 15 years and never had a hassle with Linux. They were the only online tax place back then that didn’t require Internet Explorer. You can also print your returns or save them easily in pdf format. And they’re not much more expensive than Tax Act. For my small business, it cost $91.90.

    And here’s a hint: look online for coupons. I actually ended up paying only $9.19. I locked in a 40% discount early when they offered it on Black Friday, and then I searched for other coupons when I filed. I always wait until the last week to file, as they start offering big discounts then. I found a 50% discount code and tried it. I thought it might give me an either/or with the 40%, or at best give me 50% off the already %40 discounted price, but to my surprise they stacked the discounts and I ended up getting %90 off.

  4. Mister Goldiloxx Mister Goldiloxx April 17, 2017

    “This was a problem. I wouldn’t be able to print the return from Linux, as the Tax Act program is necessary to bring up the proper forms and populate them. Actually, there’s probably a way, but I wasn’t going to spend a day figuring it out.”

    Couldn’t you print the tax returns to a .pdf (or another similar type of file), then boot into Linux and print that file to…paper?

  5. nightflier nightflier April 17, 2017

    Sounds somewhat similar to my yearly Windows/TaxAct ordeal. At least this year I remembered to boot it early and let it sit a day and do updates, so that it was usable by the time I started using it.

    This year’s hefty price increase got me too, making a note to self to research alternatives for next year.

  6. Baraboo Baraboo April 17, 2017

    Hint: Admin command prompt “slmagr -rearm” will renew your windows license for another trail period up to 4 times

  7. IP IP April 17, 2017

    You could just run windows in a Virtual machine and not have nearly as much hassle setting it up.
    As for the taxes, all of the forms and instructions can be downloaded from the IRS as pdf’s, enter the data in the fields on your computer and print them out for free. Sure you will need to do the math yourself, but it doesn’t take that long.

  8. Ghost Rider Ghost Rider April 17, 2017

    Try H&B Block Web App. This worked from Linux for me in Chromium when I tried, but does require you store your tax return in the H&R Block cloud, which may be objectionable to many. I did ultimately do mine in Windows running in a VM because I didn’t want to put that kind of info in the cloud.

  9. Lee Lee April 17, 2017

    My heart goes out to you. If Linux can’t do it I simply find another avenue. I feel fortunate that I have a tax accountant that I’ve been using for decades that never goes up on price, $40, takes my ‘shoebox’ and makes sense out of it, and in 30 minutes or less I’m back in the wind. For your sake, I’ll cross my fingers that there is not a sequel to this article.

  10. Drew Drew April 17, 2017

    Virtualbox and Windows guest has worked reliably for me. No issues with sharing my Linux USB port with the virtual Windows desktop.

  11. bigsky bigsky April 17, 2017

    Thanks Christine. Now I have the urge to go out and buy 12 beers and forget about taxes. Merci

  12. Fernando Fernando April 17, 2017

    Despite all the problems we have here in Brasil, every year the federal government releases a program in java for tax filing. I just did everything in Linux Mint 18.1. No problem at all.

  13. woland66 woland66 April 17, 2017

    Do you have anything against online tax preparation? I’ve been using TaxAct to do taxes completely online (and therefore completely in Linux, aside from the data being sent to/stored on taxact site) for at least 10 years.

  14. UncleEd UncleEd April 17, 2017

    Read this and it was deja vu all over again, remembering my grandson’s almost-installation a while back and my taxes a few weeks ago. The only place I got ahead of you this round was remembering last year. Rather than suffer the delusion I was going to go right to work, I started two days early and let the updates do their things. THEN, I installed the H&R Block software.

    It is appalling how spoiled I’ve become after using Linux for a few years. Linus, Clem, and several others ought to be ashamed.

  15. Jack Williamson Jack Williamson April 17, 2017

    I use SC spreadsheets, built up over time, and cleared of particular data but not formulas every year. Then I fill in paper forms minimally and mail them off. Easier and cheaper than resorting to software. The second year is much easier than the first.

  16. Paisley Paisley April 17, 2017

    Like everything else for sale, it’s all a matter of numbers.
    If we Linux folks are five percent of the pie–or, more likely, two to three percent, we are not going to get any attention from people who develop software. That’s the way the capitalistic world works, folks. The answer? Be a big boy or girl, and get over it.
    My answer (for me): rather than jump through the hoops outlined in this article, it was obvious that my time was worth far more than fighting that battle. A tax service now wins the battle and the war.
    (I told my ego to shut up, and get over it).

  17. David Bley David Bley April 17, 2017

    We have only 1 win10 machine in house and that resides in my wife’s domain. Due to my organization style (not) this causes some issues. So, this year, I bought an off-lease win7 machine for tax act. Every year I ask about the possibility of a version that has been tested on Wine – to no avail. I did get my taxes done, but I was floored at how much it cost for the personal version that allows for a little more complicated return.

    By the way, I figure that if the federal government spends all this $ to create all thses forms, why not just create a sw package? Seems like the tax prep industry has successfully lobbied to keep the IRS out of the tax prep business except for low income persons.

  18. Ray Ray April 17, 2017

    Long time Linux user here so I know your pain. 🙁

    A couple of tips:

    1) TaxAct does work under wine. I’ve done my taxes this way for many years. A couple of years ago my taxes got a bit more complicated so I’ve used a paid preparer since then, but I probably used TaxAct with wine for close to 10 years before that. A couple of years I had problems with the final e-submission (automated upload to TaxAct’s server) but I was able to complete this manually by finding the file on my disk and uploading it to their server (per their instructions).

    2) TaxAct lets you print your your return directly to PDF (I always do this as a final archive). You could have done this on your desktop and then transferred to Linux for printing.

    I do agree with one commenter in that I’m sure any more it’s worth all this trouble. There are reasonably-priced professionals that will do it for you and they’re well worth the money. Especially if TaxAct has really gone up to $85!


  19. Ray Ray April 17, 2017

    s/I’m sure any more/I’m NOT sure any more/

  20. Joe P Joe P April 17, 2017

    The tax prep industry successfully bought our politicians in Virginia and shut down the easy and free state tax web site. They claimed it was unfair competition. I think taxes have been a government function since Roman times and hell will freeze over before I give a private company my tax info or a nickel of income.

    I do the IRS fillable forms in Linux.

  21. Earl Earl April 17, 2017

    FWIW, at 61 I’m old enough to get the Dave/Hal reference, just so you’ll know it wasn’t wasted.

    A while back here at work a 40-something shut down a server for maintenance. As he did so I said “What are you doing Dave?” in my best HAL voice. Blank stare… crickets… not a clue.

  22. tracyanne tracyanne April 17, 2017

    Why does no one ever recommend or use any of the Linux based Accounting solutions?

    I used GnuCash for our Company, before we retired and sold the company.

  23. tracyanne tracyanne April 17, 2017

    According to

    GnuCash Free Accounting Software — Is your business powered by Linux? GnuCash is a free, Linux-based accounting software that has all the features small businesses need to manage their finances: income and expense tracking, double-entry accounting, financial reports and calculations, scheduled transactions and more. It can also track bank accounts, stocks, bonds and mutual funds. In addition to Linux, GnuCash is also available on Android devices.

  24. Thad Thad April 17, 2017

    @tracyanne Thanks for the heads-up; I’ve heard of GNU Cash but didn’t think of trying it this year. (Used TaxSlayer.) Maybe next time.

  25. Dimitris Dimitris April 17, 2017

    Would it not be easier to go to
    Select SumatraPDF (for a viewer) and PDFCreator (for printing to PDF Documents) download the little app, then run it and let it install those two programs for youm then print your taxes as a PDF?

    After that you can make sure your printouts look ok by reading them with SumatraPDF (and then either emailing your PDFs to yourselves or moving them to a usb thumbdrive that can be read by Windows 10?

    As an alternative to thumbdrives you can use a shared folder.

    BTW have you tried said Tax Software with the latest version of WINE (or even CrossOver Linux)? If you know what dependencies are needed, then there’s a good chance you can make it work on GNU/Linux instead of Windows.

  26. Eddie G. Eddie G. April 17, 2017

    As I’m not one for personal torture, I let my tax-man do all my taxes, he’s reasonably priced, and I never, EVER have to worry about Windows stealing time out of my life to jump through their hoops. My condolences to you Christine, here’s hoping by next year tax-time, you’ll have something more concrete and less troublesome to get through your paperwork.

  27. Remco Siderius Remco Siderius April 18, 2017

    In the Netherlands we had a Linux version of the official tax program already for about 10 years ago. Worked great
    (Since a couple of years taxes are online only).

    Remco Siderius

  28. DocB DocB April 18, 2017

    😀 that story made my day, wonderul!
    Reminds me of my son, who’s gaming PC (the only one running Windoze in the
    house) was fricked up again and needed a reinstall.
    It took me 10 minutes to install Tumbleweed on it to check that the hardware
    is fine.
    He spend more than 2 weeks trying to get the W7 Pro/Home/home whatever Version
    to run with any of the (unused) license keys we have from the biz hardware.
    Tons of missing drivers, blue screens, not working mouse etc…..

    Now I know why all big companies run Windows – they can afford the support
    team for that. As a small company or private person, you need something that
    just runs. And that is not Windoze.

  29. Juan Juan April 18, 2017

    I was laughing half way through it. Had samr issues in my country a while back. The stupid tax system would only work on Windows and the web version on IE and an old version. So I kept a virtual machine just for that.

    Finally they put their act together and the new web interface works on any browser running from Linux.

  30. Z_God Z_God April 18, 2017

    Here’s another tip. You could move to the Netherlands. The tax software is provided by the government. It used to be a x86 GNU/Linux application as long as I’ve been filling taxes and now it’s a web application that works fine in Mozilla.

    I’m surprised there are countries where you pay for the software to file taxes.

  31. chuck chilcote chuck chilcote April 18, 2017

    I don’t understand why you can’t use tax act in Linux. I’ve been using it(tax act) to file my taxes for the last 10(ten) years. I have been running Linux exclusively for over 15 years.

  32. Christine Hall Christine Hall Post author | April 18, 2017

    @chuck chilcote You’re using it online, where it works just fine in Linux. However, you have to pay separately for each and every return you do. As I do returns for several family members, as well as myself, I use the downloadable version, which allows you to complete as many returns as you need, although only five can be filed electronically.

  33. Mike Mike April 18, 2017


    > “I’m surprised there are countries where you pay for the software to file taxes.”

    In the U.S., the companies that make tax software have spent millions of dollars lobbying (bribing) government to prevent easy to use free software options for filing taxes. They try to introduce legislation preventing the government from ever being able to offer such a system. Any attempt at a sane, easy to use system is treated as government overreach and blocked in the name of all-mighty capitalism.

    Be glad you live somewhere less insane.

  34. RService RService April 18, 2017

    Two thoughts–

    1) Be aware that any money you spend on tax preparation is deductible;
    2) The IRS has very rational accommodations (you can still request an extension via IRS Form 4868) for the granting of (basically completely automatic) filing-extensions, as long as you send a reasonable estimate of the money you owe (here’s a quote from a search on “extension of time to file your tax return”):
    “…You can also get an extension by paying all or part of your estimated income tax due and indicate that the payment is for an extension using Direct Pay, the Electronic Federal Tax Payment System (EFTPS), or a credit or debit card. This way you won’t have to file a separate extension form and you will receive a confirmation number for your records.”
    Always keep the “Extension” trick in mind; it’s painless, it gives you an additional six months to procrastinate, and it’s one of the few paths left to a calm life.

    “DON’T PANIC”–Douglas Adams; The Hitchhiker’s Guide to the Galaxy.

  35. Z_God Z_God April 19, 2017

    @Mike, damn I and thought checking whether the prefilled in stuff was correct every year was a lot of work.

  36. Thong N Thong N April 20, 2017

    I can relate to this. Back in 2010 I opted the following at tax time.

    1) I would donwload the free virtual machine from MicroSoft:

    VM is good for 90 days, and you can extended by issuing “slmagr -rearm” at the admin command prompt.

    2) Run my updates and this could take hours.

    3) Install the Tax software.

    4) Once my taxes are done, I would print to PDF and copy the saved Tax return to a USB and burn the data to a DVD disk.

    I know, you have to learn how to us yet another OS, but this works for me.

  37. mikef90000 mikef90000 April 22, 2017

    I filed Federal using the IRS downloadable PDF forms just fine. Unfortunately, some of the California 2016 forms were created improperly and could not be viewed on *any* Linux PDF reader; had to resort to WinXP and the great PDF-Xchange to complete those.

    To add insult to injury, Foxit was sold to a Taiwanese firm with Clueless programmers who regressed v2 into tabless whereas v1 had tabs. Grrr.

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