This can happen for several reasons. One possible reason is that your captioning software is not connected to iCap properly- please refer to the section on using the Test Serial Port feature to solve this problem. If you are not able to see your data in the Test Serial Port window, then you will not be able to see it in the monitor window either, and it will not go to the remote encoder. You will need to press "Stop" to stop captioning On-Air before you can use the Test Serial Port window.
Another reason this may be happening is if you have not pressed the "Start" button to become the On-Air captioner. Check if your Status window says "On-Air". If it does not, press the "Start" button and then try again.
If you pressed the "Start" button but your Status window no longer says "On-Air", check your chat messages. It is possible that another user has pre-empted you as the live captioner. If you believe this was an error, you can press the "Start" button again to take control back, or send a chat message asking why the other captioner has signed on.