Mac OS X: Forcing Dock Applications to Open Files

Let’s say you’ve got a file that you’d like to open with a specific program. An easy way to accomplish this is to drag the document down and drop it on the application’s icon in the Dock. The icon will turn gray as you hover over it with your file, indicating that the program can at least attempt to open what you’re asking it to. But what if you want to force an application to open a file that it says it won’t? You can’t trust those pesky programs to know what’s good for them, so here’s how you make ’em do what you want.

If you hold down the Command and Option keys together before you drop the file on the Dock icon in question, this will make the program attempt to open the file. You’ll note that doing so will turn the icon obediently gray.

Here’s Billings before I held down the magical keyboard combo.

And here it is after. You WILL do as I ask, silly Billings.


If the program succeeds in opening it (and you want the same to always happen when you double-click on that file), right- or Control-click on the file within the Finder to reveal its contextual menu. Hold down the Option key with that menu open, and you’ll see the “Open With” choice change to “Always Open With.” You can then either choose your preferred application from the available list, or if it doesn’t show up there, you can click “Other” and select it from the rest of your applications. 

If you hold down Option while you’re using this menu, “Open With” will change to “Always Open With.” 


Also, if your program’s icon is grayed out within the “Choose Application” window that follows, you can switch the “Enable: Recommended Applications” drop-down menu to “All Applications.” Make sure “Always Open With” is toggled on in that box, too, and you and your opening-in-a-weird-way document will have a happy life together.