There are times you may want to start multiple items on your Surface device, such as a spreadsheet or photo editing program or a series of workstation tools. Here is how to launch multiple Apps and Desktop Programs with the Surface Pro pen button: Create a batch file: 1) Right-click Desktop, New, Text Document 2) Write the names of Apps you wish to launch, ending with the colon : symbol, or full path names to desktop programs 3. Save as (All Files) PenLaunch.bat or other name of your choice, ending with ".bat" You may move this file to another folder somewhere on your Surface computer. Configure the Pen: Now start the Surface App, and direct the pen button function to that file. Find the batch file you created by browsing to the folder where you placed it, and type *.bat Just to demonstrate, here is an example which launches Paint (Desktop Program) and Netflix (App) by holding in the Surface Pen eraser button. Tips: - To get the path to Desktop Programs, choose More, Open file location on the item in your Applications list or on the Tile. - A cleaner-running batch file has @echo off as the first line, and exit as the last. Name your programs between these two. - It is possible to pair more than one Pen to a Surface Book or Surface Pro 4. It is not known whether the pens may be configured separately, however. - Start the PC Settings app with this line: Code: Explorer.exe shell:AppsFolder\Windows.ImmersiveControlPanel_cw5n1h2txyewy!microsoft.windows.immersivecontrolpanel - Other settings you may want to associate with the pen buttons are here by @leeshor : HowTo - How To and Master Help Guide for the Surface Book | Page 2 | Microsoft Surface Forums Enjoy!