Hi Ben, I've successfully used Flrig + Fldigi for CW with my Kenwood TS-570 two different ways.
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The first is with Fldigi Op Mode = CW and a rig mode = CW. This produces an actual CW signal from the radio. For that to work, I have to enable this setting:
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The second way is to produce an audio tone with Fldigi Op Mode =CW, but with a rig mode = USB. I believe this is what is often referred to as Modulated CW (MCW), basically an audio tone mimicking a CW signal. The setting shown above (CAT Keying) needs to be turned OFF for this to work.
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Hopefully that will help!
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Cheers,
Steve K4RVA