Context menu - Combine Files: How to add shortcut and save no-questions ask?

Hey Adwul,

Maybe a little late, but I was looking around for a similar way to do this as you are, and found that using AutoHotkey is a pretty handy way to do this https://www.autohotkey.com/

AutoHotkey is a powerful little FREE tool that allows you to program specific key/mouse combinations along with a few other little effects that has definitely made my life easier, both professionally and at home. 

Once you've gotten familiar with AutoHotkey, you can make a new AutoHotkey script with this simple script in it to work through some of the steps of your problem.

^F10::
CombineFilesInAcrobat(){
     Send, +{F10}
     Loop, 4{
           Send, {down}

           Sleep, 50

      }
      Send, {Enter}
}

For a quick explanation of what this code means:

^F10:: - This is the hotkey combination that will execute the code below it when you press Control + F10 on your keyboard. You can choose any key combo you like, though be sure not to pick something that is already a hotkey you may want to use! I picked ctrl+f10 because shift+f10 is the windows default hotkey to open the Context Menu (same as right clicking)

CombineFilesInAcrobat(){ - This isn't stricly necessary, but it makes the following block of code into a function that can be easily called elsewhere.

Send, +{F10} - Acts as though you've pressed Shift+F10 on your keyboard, opening the context menu. 

 Loop, 4{
           Send, {down}

           Sleep, 50

      }

The Loop, 4 means that it will execute the next block of code 4 times. Youll need to change the 4 to however far down the context menu the option to Combine Files in Acrobat is when you right click a PDF. For me it's the 4th option, so I put 4. It will then press the down button on your keyboard, and then wait 50 thousandths of a second. For troubleshooting, it can be easier to change 50 to a bigger number so you can see what your computer is actual doing if it's not what you expect. You can also probably get away with no wait here, but I often like a wait in this type of program because it allows me to see what's happening, while still being nearly instant.

Send, {Enter} - Hits enter. Since we've moved your selection to Combine Files in Acrobat in the last block of code, this will combine the files in acrobat, and bam, you're done!

That was as far as I needed to go (I often need to reorganize the order of my files before hitting combine, so I don't want that step automated) however, I imagine with a bit of research on how to use autohotkey, you could get to step 8 pretty easily in a single keystroke sequence. Add a bit of a Sleep after you've gone as far as I have to give adobe time to combine your files, Then either find a hotkey to press "Combine" or you may have to find the mouse coordinates of the button, and have autohotkey perform a mouse click at those coordinates, etc. 

Hope this helps!