Can I press two 8-way analog inputs simultaneously?

I am using a controller on Windows 10. I can use 8-way input, but it won't press two of the 8 directions simultaneously. Can I make it press both simultaneously or else give it 16-way input? I'd rather just be able to make it press simultaneously, but either would work. I'd like to think I could do it with AutoHotKey, but I am not savvy enough to know, although I would bust my *** if it was gauranteed to make it work.

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