CHIRP

Could you please provide a debug log as described in the Wiki: "How To Report Issues"? Thanks!

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This looks like a cable issue, not so much like the problem described and resolved in #2019.
Please refer to these Wiki articles:
CableGuide
CableGuide FTDI OEM Cables
[RTSystemsCablesAndMavericks]
If there's no solution to be found in any of them, please read: How To Report Issues and provide a debug log. Thank you!
Windows notes: If you are using a generic cable with a Prolific chip, you will very likely need to downgrade your driver to version 3.2.0.0.
It can be found at http://www.miklor.com/COM/UV_Drivers.php
MacOS notes: this OS is apparently very picky about USB to Serial cables. From what I heard, only (genuine) FTDI-based cables can be made work.
You must have the KK7DS Python runtime for Mac OSX installed.
Also see MacOS Tips!
Linux notes: Linux generally is quite good with USB to Serial converter drivers. The most likely cause for grief is a connector which doesn't provide good electrical contact.
Bluetooth notes: connections often suffer from timing issues, please try a cable instead.