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I want to teach my son to not click unsigned software. Unfortunately there some software that's highly useful (e.g. Search Everything, but it could be any other software) that's not digitally signed.

Since I own a code signing certificate, I could sign the executable myself. This would change the UAC dialog to look "secure". While I'd apply such a change locally on my and my sons computers only, what could be the impact if this modified software leaves my PC and becomes available in the Internet?

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First of all I'd be very careful in declaring all signed software as save since malware with valid signatures already exist and you can expect that the amount of signed malware will increase.

Second, there's a pretty good answer for this question here.

I want to add that a possible solution for your scenario would be creating and installing an own root certificate. This would save you from any trouble if you accidentally sign malware.

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