> We think we can mitigate those concerns some by code-signing the exe, having the download from https, and building a recognized brand.
I don't see how all these resolve someone sending an email that looks exactly like yours, which links to a page that looks exactly like yours, which links to a malware executable.
Even with code-signing I wouldn't trust non-technical users to understand difference between popups, as well as resist close-all-these-annoying-popups reflex.
To make sure that the email is legitimate I'll have to either check the source, or seek in the mouse over. And after it is a "recognized brand", no one will be checking that.
I don't see how I could feel safe with executable file download links in the email. Maybe registering a scheme and sending in email a link with instruction to the file origin would be more acceptable, but that's only if the software is already installed. Ex: wirefrom://my@email.com