How to Fix 404 Errors When Running apt-get update on Debian Lenny: A Complete Guide for Legacy System Maintenance


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When working with Debian Lenny (5.0), a long-EOL release, you'll encounter 404 errors during apt-get update because the official repositories have been moved to archive servers. The standard repo URLs in your sources.list no longer work.

Replace your current /etc/apt/sources.list with these archive URLs:

# Debian Lenny Main Archive
deb http://archive.debian.org/debian/ lenny main contrib non-free

# Debian Lenny Security Updates
deb http://archive.debian.org/debian-security lenny/updates main contrib non-free

# Debian Lenny Proposed Updates
deb http://archive.debian.org/debian lenny-proposed-updates main contrib non-free

You'll need to modify APT's behavior to work with archived repositories:

# Create or edit /etc/apt/apt.conf.d/99archive
echo 'Acquire::Check-Valid-Until "false";' | sudo tee /etc/apt/apt.conf.d/99archive

After making these changes, run:

sudo apt-get clean
sudo apt-get update

You should now see successful repository updates instead of 404 errors.

For package installations, you might need to force specific versions:

sudo apt-get install package=version

Example for installing an older version of openssl:

sudo apt-get install openssl=0.9.8g-15+lenny16

For production systems, consider upgrading through supported releases:

lenny → squeeze → wheezy → jessie → stretch → buster → bullseye

Each step requires careful planning and testing.

  • Debian Lenny reached EOL in February 2012
  • Security updates are no longer available
  • Consider migrating to a supported release
  • For legacy applications, containerization might be a better solution

Debian Lenny (5.0) reached end-of-life (EOL) on February 6th, 2012, which means official repositories have been moved to the Debian archive. The URLs in your current sources.list are attempting to access non-existent locations.

Here's the corrected configuration for Lenny repositories:

# Debian Lenny Main Repositories
deb http://archive.debian.org/debian/ lenny main contrib non-free

# Debian Lenny Security Updates (frozen)
deb http://archive.debian.org/debian-security/ lenny/updates main contrib non-free

# Debian Lenny Proposed Updates (frozen)
deb http://archive.debian.org/debian/ lenny-proposed-updates main contrib non-free

1. Backup your current sources.list:

sudo cp /etc/apt/sources.list /etc/apt/sources.list.bak

2. Edit the file with your preferred editor:

sudo nano /etc/apt/sources.list

3. Replace contents with the updated configuration above

4. Run apt-get update:

sudo apt-get update

If you still encounter issues, you may need to modify your APT configuration to handle the outdated Release files:

# Create or edit the following file
sudo nano /etc/apt/apt.conf.d/99ignore-release-date

# Add this content
Acquire::Check-Valid-Until "false";

For systems that must remain on Debian Lenny:

  • Consider setting up a local mirror of the archived repositories
  • Look into third-party repositories that still maintain Lenny packages
  • Evaluate upgrading to a supported Debian release

When necessary packages aren't available, you may need to:

# Download .deb packages manually
wget http://archive.debian.org/debian/pool/main/p/package/package_version.deb

# Install with dpkg
sudo dpkg -i package_version.deb

# Resolve dependencies
sudo apt-get install -f