Solution

Wireless & IoT
1

Solution found! So while using the Experimental WiFly Arduino Library, inparticular the WiFly_Autoconnect_Terminal pde, I needed to comment out this part.

  if (!WiFly.join(ssid, passphrase)) {
    Serial.println("Association failed.");
    while (1) {
      // Hang on failure.
    }
  }
  
  Serial.println("Associated!");

with that out of the way I was able to connect using terra term, NOT the built in arduino serial monitor. Using Terra term I was able to input the $$$ to get into command mode.