Generic raspberry pi setup fails update

Running the second step of the update process returns:
Error: Unable to complete update, please contact support

Please send us the token generated by

pihole -d

or do it through the Web interface:

Sent. The automatic upload failed so I used the tricorder method

pi@raspberrypi:/var/log $ echo "hello developers" | pihole tricorder
https://tricorder.pi-hole.net/txp7u4ieyq
pi@raspberrypi:/var/log $
pi@raspberrypi:/var/log $ cat pihole_debug.log | pihole tricorder

What version of Raspbian are you running?

You have 131 packages out of date, have you ever updated the OS?

I updated the device, rebooted and ran the installer again it failed at the same place.

Here's the new token: https://tricorder.pi-hole.net/fto6i7bfwt
Linux raspberrypi 4.9.35-v7+ #1014 SMP Fri Jun 30 14:47:43 BST 2017 armv7l GNU/Linux"

And no, this thing has been rock solid since I set it up ages ago, I hardly ever touch it, it's great!

Here's the Raspbian info: "Linux raspberrypi 4.9.35-v7+ #1014 SMP Fri Jun 30 14:47:43 BST 2017 armv7l GNU/Linux"

You're running Jessie, Raspbian 8, which has been out of support since 06/17/2018. Current Raspbian is version 10, Buster.

Thanks, I found the update steps and am running them now. Appreciate the help!

-Dan

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