This is somewhat related to How to avoid Outlook security alert when reading outlook message from C# program.
I use MyPhoneExplorer to manage my cell phone, but whenever it syncs with Outlook I get that pesky message box every time. I am getting tired of both hunting down that checkbox / button combo and to answer the same thing over and over.
Asking me once is fine. Keep asking me is fine when I haven't decided anything. But when the Office team forgot to ask me if I always want to allow this certain program, I wonder if there are some other settings to tweak, hidden somewhere?