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how to open .exe file

Hello all, I'm using monterey 12.1 on my 2019 macbook pro. I have outlook for mac due to work necessities. I need to open an exe file. Based on what little I have read, I might be able to use bootcamp but I would have to reboot everytime I need to open an exe file. Seems like a hassle. Also, I don't know if that means I could manipulate the file, save it, and send it. Would I have to switch back to mac os to send it? Can anyone advise if there is something better than bootcamp I should use? Hopefully free but I need to be able to do more than just open the file and look at it. Any assistance is greatly appreciated. Thank you in advance!

Posted on Jan 8, 2022 1:46 PM

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Posted on Jan 9, 2022 3:33 PM

22cowboy wrote:

My new CPA sent me a zip file. When I opened it, it was a .exe file. He explained it's simply to make completing taxes easier.


If this message really is from the CPA: I’d be inclined to find a different CPA, and one a bit better about security. Here, by either telling you ahead that you’re going to get this tool, or by providing a download link to the CPA’s own website.


If this is not from the CPA: this is a very common technique used for phishing and ransomware. This is one way how systems get pillaged.


Sending email addresses can be trivially spoofed, too. Don’t depend on that as evidence of authenticity.


Mailing around executables is Really Hazardous, and zips and particularly zips containing exes are routinely dropped by many network firewalls.

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Question marked as Best reply

Jan 9, 2022 3:33 PM in response to 22cowboy

22cowboy wrote:

My new CPA sent me a zip file. When I opened it, it was a .exe file. He explained it's simply to make completing taxes easier.


If this message really is from the CPA: I’d be inclined to find a different CPA, and one a bit better about security. Here, by either telling you ahead that you’re going to get this tool, or by providing a download link to the CPA’s own website.


If this is not from the CPA: this is a very common technique used for phishing and ransomware. This is one way how systems get pillaged.


Sending email addresses can be trivially spoofed, too. Don’t depend on that as evidence of authenticity.


Mailing around executables is Really Hazardous, and zips and particularly zips containing exes are routinely dropped by many network firewalls.

Feb 4, 2022 4:11 AM in response to 22cowboy

If Im not mistaken you can run windows as a VM on M1, M1 max and M1 Pro machines. These machines can't run windows natively (because Microsoft isn't supporting windows on Apple Silicon natively and may never do), but you have a 2019 machine so you don't need to worry about that since your machine has an intel processor.


If you don't want to install windows natively there are workarounds. there are programs that can open or convert the files for you like wine or the code weavers crossover app that someone else here recommended or you could install windows as a VM (virtual Machine, that way you don't need to reboot your device to use both OS's. It basically makes windows an app and you can have it in a app "window" if you will haha, pun not intended :). This is what it looks like.


The program in this image is parallels, which is a piece of software you've to pay for. Im not sure what's available that's free apart from wine.



Jan 8, 2022 2:00 PM in response to 22cowboy

There’s no direct means to run a Microsoft Windows executable in macOS. Your options are to install Microsoft Windows using Boot Camp (on Intel Macs only, not an option on Apple silicon Macs with M1 processors), or maybe running the app via the CodeWeavers CrossOver app, or running Windows as a guest on another server somewhere. Or finding an alternative to this particular Windows app, of course.

how to open .exe file

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