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I am using a TMS570 MCU with this debugger which has the 20-pin cTI JTAG pinout exposed in this page.
Should all the GND terminals be connected to the board's ground or it is sufficient just one?
They would have written NC if you only had to connect one.
The purpose of these grounds is to interleave signal wires with ground wires in the ribbon cable so no signal wire neighbors another signal wire.
This reduces crosstalk.
Required, but never shown