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It's actually complicated since most of the environment now is based on newer jailbreak, assuming you have MRPI, MKK and so on already on the Kindle.
My Kindle had nothing of it, just plain base 2014 jailbreak!
Anyhow, upgrading to firmware 5.3.7.3 actually works.
I managed to upgrade usbnet to 0.22.N and solved also the timeout error along with the modded root password.
Long story short: if you have 5.3.7.2 firmware, move to 5.3.7.3.
Thank you!
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