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Dufur, OR | I use freeform all the time. On your first picture, on the 4 buttons under where it says freeform, the round button is "record". It appears to not be toggle on. Manually press it and should draw a red line behind you.
With that said, you do have freeform recording set to "record when logging" which should toggle that on when you are applying. Appears you are not using field iq so just manually toggling on coverage? If so toggle coverage on/off and it should trip on the record button. Either way works. Main thing that record button needs to be on which will result in a red line being drawn behind you.
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