Running Windows on Mac

I went through this a few years ago - I need to run Quickbooks and now Quicken for Windows. (I know, yech).

I bought a refurbished laptop with Windows as it was less than buying Parallels and Windows.

Here I am 3 years later, using the machine more than I was before and ready to throw it out a window. So I’m back to my original question - does anyone have experience with running Quickbooks and Quicken in Windows on a Mac? I got Crossover in a recent Macheist sale but I’m not sure that will work to install either of them. I had Parallels or the other years ago, on my first iBook but it was so long ago I’m not sure it’s upgradeable.

Please, save me from buying another Windows machine! What are some options?


ps - this got bounced for having 14 characters with it’s original Windows on Mac subject

I have been running QuickBooks for Windows via VMWare Fusion (now with Windows 7) for many years now on a succession of MacBook Pros with no real problems.


Codeweaver’s information about Crossover and Quicken 2018 is that it runs well but not so well for Crossover and QuickBooks.

I use the free Virtualbox instead of Parallels or VMWare Fusion to run Windows in a virtual machine. With any VM software, instead of keeping files inside the guest OS volume, I recommend keeping your files on the Mac filesystem and use the VM software’s ability to share a folder between guest and host. If a particular Windows application doesn’t work well with files within such a shared folder, use something to regularly copy the files from within the guest to the host (copy be a Windows script that copies files, could be something like Dropbox or Google Backup & Sync running on Windows).

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This is where I smack myself in the head!!

I installed Virtualbox on the iMac a couple of weeks ago, so I could run Snow Leopard in a Virtualbox. Doing a Mac to Mac folder share is problematic (they admit it’s experimental at the moment).

I would need a copy of Windows 7 to install right? I never got one with the machine I bought but I think I can download an ISO for it now that I have the key activated. Do you think a refurbish key will run in a system like that?

I wish I could figure out what’s wrong with the laptop. It’s slow as molasses, hard drive checks out fine and I am trying to check for viruses now.

David - does VMWare Fusion come with a version of Windows, or do you need to buy that separately? I tried to contact them when I was deep in my project 2 weeks ago and it was actually impossible. Which is why I went with Virtualbox.


You have to have your own version of Windows, the same as with any emulation software.

I am glad to answer any questions I can, but VMWare Fusion also has a fairly active discussion forum.[published]~objecttype~objecttype[thread]


To keep things simple and avoid possible complications, I keep my QuickBooks company file in Windows (via VMWare Fusion), but frequently back up the file to a shared folder.


I have used parallels Desktop for Mac since about version 3 with guest OSs including Windows XP Pro, Windows 7 Pro, and Windows 10 Pro along with many versions of OS X and macOS. My Quicken on Windows use dates from more than 15 years ago. Even with the subscription mode now with PDM, It is still less expensive of time and dollars than any physical Wintel machine. The real bonus is that my Quicken backup files are in my macOS home directory and are backed up hourly by Time Machine. The Virtual Windows machine itself is backed up by my CCC backup of my boot drive and can be instantly restored by Finder copy.

My Windows VM is unaware that the host machine has changed from HFS+ to APFS. In fact, I never thought about HFS+ vs APFS for the Windows VM since I just started it and it worked after every APFS update since macOS started converting.

Having no direct experience with Fusion or Virtualbox, I can not comment on them. I only note any that any Windows OS installation must be properly licensed.

Yes – and if anything goes wrong with the Windows installation, just delete the VM file and copy the latest backup.


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OK. Have a client that is a 20+ person firm and the bookkeeper has been running QB Pro in a VM on a Mac for a decade or so. Works fine 99.9999% of the time. (Which matches or beats real Win.) Currently on Win10.

In this and other such situations we find consistently when we compare that Parallels gives a better user experience than VMWare Fusion. (But we tend to use Fusion for server type setups.)

We I do is install Win on the “C” drive. Then create 1 or 2 more drives for the Win side. One I call D: (Data) and that’s where all the files go. That (the Mac file/folder that pretends to be the D: drive) is what we back up on the Mac side every day. The VM we backup once every month or few. If it dies we put back the latest copy we have and let it update itself for a bit. Before we moved everything to SSD I also created an S: (Swap) drive and put the page files there. That way they didn’t bloat the Mac file/foder setup that was the boot system.

As to Windows I’m sure we bought it from a place such as CDW or similar. But I think Parallels and/or Fusion give you an option to buy a copy at retail pricing when you set it up. Both have a trial period lasting 2 week to a month.

Regarding acquiring and running Windows, you can download Windows ISOs from Microsoft. The Windows 7 download requires a valid product key but Windows 10 does not. How to Get Windows 10 for Free (or Under $30) covers license options. I was interested to learn that you don’t give up much by running Windows 10 without ever activating it.

A lot of people don’t like Windows 10 because of its defaults sending data to Microsoft and (eventual) “forced march” approach to software updates. But support for Windows 7 is ending next year and the Windows 10 settings can be changed.

This is why I (reluctantly) switched over to running Windows 10 via Parallels Desktop last year, rather than Windows 7. While I’m not a fan of 10, at least it’ll still be getting security updates this time next year. And with Parallels I can launch Windows apps directly from Spotlight or Alfred, bypassing the Start Menu altogether, and use them alongside my Mac apps.

(Parallels Desktop user since version 7.)

Excellent advice here; we, too, run Windows 7 in Parallels for Quickbooks Pro 2016; we store the files in a shared folder on Mac – which is actually in Dropbox for further backups and allows for multiple Macs to access the same files from the same or different locations (just not simultaneously, or course).

We find the QB running in Parallels is a better experience than VMWare Fusion, because of the way Fusion captures and requires you to hit Control-Option to release the cursor back to Mac.

The VMs are also much easier to restore from CCC backups than Fusion, which can be persnickety when you move/copy a VM; Parallels basically just says OK.

The Coherence Mode isn’t to everyone’s taste, but one of our bookkeepers prefers it.

I find Fusion to be slightly faster booting or doing much of anything else in Windows 7, but if its just about QB, then once you’re booted and running QB, who cares; it’s data entry.

I would also caution you not to get in the habit of merely suspending a VM without occasionally rebooting – it’s Windows, after all.

Finally, in adition to the advice not to pay over $30 for Win 10, do not pay over $25 for Win7 – in fact, you should be able to use the product license from your laptop, should you desire to actually just throw it out the Window. (sometimes it can be tricky, depending on the license code series, to get an OEM ID to take with a modern ISO, but it’s worth a try; short of that, you can make an ISO from your laptop restore disk or volume that Parallels will accept – but dat taks teh skilz.)

I use VMware used XP for years, then purchased Windows 7 from a reseller and installed anti-Windows 10-upgrade software; a couple of years later did the did the dance of accepting the free upgrade of Windows 7 to Windows 10, then downgrading back to 7. I have the same experience of the other VMware folks above. I keep my Quicken file on a shared drive (that is, on my Mac system drive, which is backed up by TimeMachine, and almost every day by Carbon Copy Cloner to a bootable clone drive. I have never had any trouble. (There is an irritating delay of a few seconds where Windows 7 says it can’t mount a shared drive. That may simply be because I am using a slow-by-today’s-standards Mac Pro (2010).

I recently purchased a 2-year Quicken 2018 Premier from a reseller. The upgrade went without a hitch.

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VMWare Tools, like Parallels Tools, is guest software that allows seamless movement of the cursor between guest and host as well as other features that help with interoperability between guest and host operating systems. Virtualbox calls its comparable software “guest additions.” VMWare and Parallels even have tools for running in a guest macOS but Virtualbox does not.

VMWare Unity mode and Virtualbox Seamless mode are comparable to Parallels’s Coherence mode; all can run Windows as the guest OS but make Windows applications look more like they’re running beside Mac applications instead of everything being contained within a Windows desktop window.

frederico wrote: “We find the QB running in Parallels is a better experience than VMWare Fusion, because of the way Fusion captures and requires you to hit Control-Option to release the cursor back to Mac.”

This is only (partly) true if you don’t install the VMWare Tools, which one should do anyway because that’s also what provides a shared clipboard, lets you drag files in and out of the VM, and many other integrations.

“The VMs are also much easier to restore from CCC backups than Fusion, which can be persnickety when you move/copy a VM; Parallels basically just says OK.”

At least with the more recent Fusion versions (8? +), it just asks if you’ve moved the VM or copied it. Click a button and done.

What I disliked most about Parallels back when I used it, which may not be true anymore, was that it installed a number of background processes some of which kept running even when Parallels wasn’t supposed to be active, and they could run amok. It was also difficult to remove it completely–IIRC there was even a step that involved booting to single user mode and command line.

One potential price advantage for Fusion is that the license allows personal users to install it on multiple macs which I’ve found to be very handy. Parallels requires a separate license for each mac.

Unless things have changed with versions newer than 8.5, a Mac or Win7 VM requires you to release the cursor using Command-Control in Window mode; this I’m sure is not the case for Unity; I never use it. And, yes, I have VMWare Tools installed.

If you know a trick to override this behavior with 8.5, please let me know.

Yes, restoring a disk by clicking ‘moved’ or ‘copied’ seems like it should work flawlessly (and that feature has existed at least since v4), but I can’t tell you the number of times I’ve had to reinstall VMWare Tools and reset network configurations and generate new MAC addresses when all I did was move the image from one drive to another (and yes, I tried both options; sometimes it is, as I said, persnickety).

Yes, I agree, the liberal personal license (does not include Enterprise or Commercial and not always Education) is a definite bonus for families.

And one thing I love most about VMWare is they don’t shove misleading ads for annual updates down your throat; something Parallels does every single year, trying to lead you into believing you must update with macOS annually. I can’t tell you the number of clients/peers who are misled and extorted at $50 a pop every Winter, or have signed up for the expensive subscriptions.

Win7 will run for 3-4 years at a time in Parallels versions; one need only upgrade if one needs to also upgrade the guest OS and wants flawless support for all new features (or updates Mac hardware to a version that Parallels doesn’t support the parent OS).

Heck, I’m even running Mojave in Fusion 8.5; it’s not perfect, but its good enough. That said, I’d happily update Fusion to 10 or 11, but it won’t run on my unkillable 3,1. [sad trombone]

I need to run Quickbooks and now Quicken for Windows. (I know, yech).

Please, save me from buying another Windows machine! What are some options?

Do you absolutely HAVE to run Quickbooks and Quicken? Have you looked at this Macintosh program as a replacement for Quickbooks:

Free video tutorials:

And/or this Macintosh program as a replacement for Quicken:

Both programs have garnered a lot of praise from Mac users who were fed up with Quicken and Quickbooks being second class citizens to the Windows versions.

Hi Randy - yes, because they are clients and I am in charge of their files.

I have a few other clients I remote into (also Windows) but at least I don’t host the files. But for three of them, I do.

I am reading the Quicken replacement stuff with interest. Only a matter of time before my own Quicken 2007 stops working.


I have using QB running on Win 7, and later Win 10 under Parallels in a multi-machine LAN with multiple people using the product on different Macs. This setup has occasional annoying problems. yesterday, one of the virtual machines decided to create it’s own IP and it couldn’t see the QB Server or any other machines. Had to find the setting in Parallels that magically changed itself. I also dislike that Win 10 does not give you any control of when updates are installed (AFAIK). And updates sometimes mess up settings. very frustrating. In our multi-machine environment, at the start of every day, we check to see if updates are available for Parallels and Windows, and we install them on all machines at the same time so that we know what is running. We always Shut Down windows at the end of the day.

I have also run QB on a dedicated Windows machine with WIn 7 for my home. If you don’t need multiple users on QB, this is my preferred setup. It is simple to set up and manage. The Virtualization layer adds complication and it is annoying to figure out what broke when something was updated. And Windows 10 has made it worse to manage

I find that using iCloud and Dropbox helps integrate the standalone PC with my Macs at home

Not sure, but in Windows 10, can’t you set Start > Windows Update > Advanced options > “Automatically download updates, even over metered data connections (charges may apply)” to Off?