Both the original and the community reflash image contains a pretty old Debian 8 Jessie. Due to security concerns and new software versions, it's reasonable to upgrade your CHIP to the latest Debian version.
You can also start with already running CHIP with the original software, but some have experienced problems after the upgrade, so please be careful. Less packages installed = less problems. If you just found your CHIP in the drawer, better do a clean reflash first. If you experience sudden crashes during the boot after the reflash, you may try to install the "no limit" image when starting the flashing process.
For the start, you have to be able to connect to your chip from command-line. Once you're ready, it's a good practice to perform the software management commands in screen in case your connection fails for any reason.
Please note, before you start the upgrade process, a repository change is needed, since the original NTC servers are down. You may keep the "jessie" string in the chip repo as there are no packages for Stretch or Buster available.
To upgrade from Debian 8 to 10, you have to upgrade to 9 first and then from 9 to 10 as there is no direct update script that skips releases. Please see the following guides to do the upgrade:
- How to upgrade Debian 8 Jessie to Debian 9 Stretch
- How to upgrade Debian 9 Stretch to Debian 10 Buster
Once done, reboot the CHIP and after it boots back, you may check the Debian version to make sure everything worked as desired.