Thank you for the response, Charles.

Unfortunately, I am using documents created by my worksite, and all of the checkboxes they use are of the legacy type. I am not able to create new documents or alter them.

Some of the work computers still run Windows XP and Word 2003, so I would imagine they're not going away from legacy checkboxes any time soon. My work computer just got upgraded to Windows 7 half a year ago.

I probably click on over 100 checkboxes per week, so having a solution for my specific situation would save quite a bit of time.