Reviving My Raspberry Pi 3B

… Reviving My Raspberry Pi 3B: From Jessie to Bookworm (and a Dead SD Card) …

TL;DR

Tried upgrading my old Raspberry Pi 3B, discovered it was still running Raspbian Jessie (2015!), installed Bookworm Lite, enabled SSH, and hit a wall when the SD card died during upgrade. Next step: reinstalling Raspberry Pi OS on an external drive to avoid future storage issues.

The Surprise: Jessie in 2025?

I was hoping for a quick upgrade—just enable SSH and get going. But of course, things didn’t go as planned.

Turns out the OS installed was Raspbian Jessie, released back in 2015 and last updated in 2017. What?! Honestly, I thought I had used it more recently. Time flies 😅

Installing the Latest Raspberry Pi OS

I headed to the official Raspberry Pi OS page Raspberry Pi Operating Systems for a lite environment. I want to save as much space and CPU as possible for Docker (or other lightweight services).

Using Raspberry Pi Imager
  • Formatted the SD card (32GB > FAT32).
  • Had to switch USB ports, apparently Raspberry Pi Imager doesn’t like USB3.
  • Inserted the SD card, booted the Pi… and SSH worked! Victory! 👑
Pi Imager screenshot
Quick System Upgrade… or Not

I ran the usual upgrade commands:

sudo apt-get update
sudo apt-get upgrade

But then… upgrade failed 😱

dpkg: error processing archive ... Input/output error
dpkg: error while cleaning up: unable to securely remove ... Input/output error

Even sudo stopped working:

/usr/bin/sudo: Input/output error
Diagnosis: Dying SD Card

After some research, it seems the SD card is dying. I’ll need to buy a new one—and next time, I’ll install the OS on an external drive to avoid these read/write issues.

This video might just save my life: Boot Raspberry Pi from USB

Lessons Learned
  • Always check your OS version—time flies!
  • SD cards wear out. Use external storage for reliability.
  • Raspberry Pi Imager has quirks (USB3 issues).
  • SSH can be enabled directly in the Imager—super handy.
What’s Next?

Reinstalling Raspberry Pi OS on an external drive. Stay tuned for the next post maybe this time I will progress 🤪