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Is it important whether I start up iCap or my captioning software package first?

It often is. When you are using TCP/IP Socket or Software Serial Port input modes, you need to start iCap up to begin listening on those ports before you try to connect with your caption writing software.
When you are ready to begin entering live captioning, press Start in iCap (the "On Air" indicator displays in your status window). Then begin your writing procedure in the captioning software package.
When you are finished entering live captioning, you should enter a blank-and-pass or return to upstream command in your captioning software package, and then press Stop in iCap.