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I'm looking to buy an IDA Pro license for my own home use. However, I use all three supported platforms: Windows and Linux on desktop, and OS X on a laptop. I can't afford more than one license, so I'm interested to see if other people have been in a similar situation and how they solved it.

My initial thoughts on each version:

  • Mac OS X: I use my laptop most often, but reversing on a 13" screen isn't always fun, I would not be able to use the Mac version on either Windows or Linux.
  • Windows: I've heard good things about running the Windows version in Wine on Mac and Linux, or even in a VM.
  • Linux: I almost always have a Linux VM even when I'm on Mac or Windows, so I could always install IDA in a VM.

I'm leaning towards the Windows or Linux versions to be able to use anywhere, but I've never used IDA in a non-native environment, so I'm somewhat concerned about keyboard shortcuts and integration.

Any suggestions on a good way to go?

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Your IDA Pro license allows you to install IDA on two desktops and one laptop. You might want to check the license situation if you install IDA in a "portable/VM" environment, but only Hex-Rays can give you definite information here. So i'm omitting that part from my answer. (Some Hex-Rays employees frequent this site as well).

This depends a lot on your use case. How often do you want to do some reversing work when you have your laptop, but don't have access to your (Windows/Linux) desktop?

When i'm using IDA, i want to have a lot of screen estate for it, and don't generally need much screen for the debugee. Which generally means you want IDA on your host OS, and the debugee in the guest OS, as you'll always be able to access the whole screen on the host, but maybe not in the guest, especially in multi-monitor-configurations.

Personally, i have the Linux version, and while Linux is my main desktop environment, i needed to use IDA at a customer once, that allowed only Windows in their network. I was allowed to install VirtualBox and run Linux in that VirtualBox (Host only network, no access from Linux to their net), and my IDA worked very well, using the "remote debugger" to debug stuff running on the host. So while i did miss my big screen, i was able to work without any hassle regarding keyboard shortcuts, inability to do what i needed, or crashes.

So, if you're travelling and working on your Mac laptop 95% of your time, i'd buy the Mac version if i were you, and debug Linux/Windows programs in VMs. If you're have access to desktop most of the time, and consider IDA on the Mac a kind of "emergency mode", get the version for the OS you use on your desktop most, and install a VM with IDA inside it on the Mac. In this case it shouldn't matter much if that OS is Windows or Linux.

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I have the Windows version with Hexrays, and in my experience I've had issues with the wine packages in Ubuntu (14.04 and 16.04) and macOS (homebrew) for the latest IDA version (6.9).

If you use the wine development releases (1.9.12+), then IDA works fine.

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I've been using a Windows version of IDA Pro for years on OSX through VMware Fusion. Not daily, though - yet no problems whatsoever.

Using a VM is even better because you can take snapshots of your VM before e.g. starting working with malware and revert them when you're done.

Re screen estate - nothing to worry about, VMware VMs can run full screen, using every pixel available

Remember that an OSX version of IDA Pro will likely have different (and more :)) bugs which remain unfixed for longer (at least this is my impression) than in a Windows version. Plus a bunch of plugins are Windows-only or at least barely tested on OSX, if compilable at all. Same situation, if not worse, with Linux in place of OSX.

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