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Let's say I need to use some activation software, which connects to a server and activate some other software in my PC (i.e., Microsoft Toolkit crack to activate MS Office, or a crack for a game).

Obviously I'd have to assume that one cannot ever 100% trust this kind of programs, and I'd use it on my own risk, but I'd like to minimize the options of getting infected with any malware...

So, let's say I scan this .exe file with different antimalware software like Avast, Malwarebytes and Superantispyware and them all say it's clean. And let's say I remove any firewall outbound or inbound rules I had to add to allow the program to connect the activation server...

If I do this, I can be pretty sure there's no option of being infected, or am I missing something important?

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Running any program which you can't trace back to the maker is a security risk. Using an application from Microsoft (if you sure it came from there) would be safe because you know it came from them. But any software, like cracks for games etc..., even if you scan them and they are cleared could still contain malware. SO NO, You can't be pretty sure there's no option of being infected. –  Rik Jan 12 at 17:43
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There is also an alternative to "activation software" so there really isn't a safe way, because the actual use of said software, is not intended for legit reasons. –  Ramhound Jan 12 at 18:35
    
You can a local KMS microsoft licensing server behind your firewall. Beyond big companies with local licensing servers available you are stuck. It will be almost impossible to live that way. Note: While you are scanning your PC for the next 24 hours because you wanted to install a program I will allow Assassin Creed IV to phone home and spend 24 hours gaming. Which activity sounds more fun??? –  cybernard Jan 12 at 21:27

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