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Late upgrade - LMDE 2 (Betsy) with Mate to 3 (Cindy) with Cinnamon

For those still using Linux Mint Debian Edition version 2, which is long obsolete, here are the instructions for a somewhat clean upgrade

These instructions are, in fact, a compilation from the instructions and comments from this article from Linux Mint page. Just to save you time among some common and solved issues.

These instructions assume you're using a non-root user with sudo privileges. I always find this safer than becoming root.

1. TL;DR
2. Before you begin
3. First backup and snapshot
4. Switch display manager and desktop environment to LightDM and Cinnamon
   1. Display Manager
   2. Desktop environment
5. Another backup and snapshot
6. Preparing for the upgrade
7. The upgrade

TL;DR

Install LightDM and Cinnamon, remove MDM and reboot (my system required a reboot for LightDM to fully work).

    sudo apt install lightdm cinnamon mint-meta-debian-cinnamon
    sudo apt remove mdm mint-mdm-themes*
    sudo dpkg-reconfigure lightdm
    sudo reboot
  

Test them until you're OK (and your family too, if it's the case), then remove remaining Mate packages and install remaining Cinnamon ones.

    sudo dpkg -r --force-depends mint-info-debian-mate
    sudo dpkg -r --force-depends mint-user-guide-mate
    sudo apt install mint-info-debian-cinnamon mint-user-guide-cinnamon
  

Do a backup and a snapshot. The backup procedure is up to you. Use timeshift for the snapshot.

    sudo apt install timeshift
    sudo timeshift --create
    ...
    RSYNC Snapshot saved successfully (<Time>)
    Tagged snapshot '<Name>': ondemand
    sudo timeshift --list
    ...
    Num     Name                 Tags  Description
    ----------------------------------------------
    <Number>    >  <Name>  O
  

Update LMDE 2 and install the upgrader.

    sudo apt update
    sudo apt upgrade
    sudo apt install mintupgrade
  

Set your terminal to unlimited scrolling. In terminal's "Edit" menu, go to "Profile Preferences" -> "Scrolling" - "unlimited".

Check the upgrade requisites and download packages.

    # Repeat each step until 100% satisfied, fixing everything it tells you
    mintupgrade check
    mintupgrade download
  

Update your backup and do another snapshot.

    # Again, the backup part is up to you
    sudo timeshift --create
  

Upgrade LMDE!

Note the packages it will remove - you might want some of them back afterwards

    mintupgrade upgrade
  

Review overall settings. In my case, I had to reenable 'Manual login' and disable 'Hide user list' in Main menu - Administration - Login Window - Users.

When fully satisfied with the results, remove the snapshots.

    # If you want to select snapshots to remove
    sudo timeshift --list
    timeshift --delete  --snapshot '<Name>'
    # If you want to remove all snapshots
    timeshift --delete-all
  

Done.

Before you begin

Before you start thrashing in the shell, let's have a couple important things in mind:

• Linux Mint Debian Edition is not a rolling release distro. So, the only pain-free upgrade scheme is a fresh install. The upgrade recipe and tools are a incredibly great work from Mint mantainer Clement Lefebvre for those who prefer not to wipe the system partition. But it's not trivial - you have been warned.
• LMDE 3 comes with LightDM display manager and Cinnamon desktop environment, and the upgrader requires them. You can switch back later, but you'll have to go for LightDM and Cinnamon for the upgrade.
• You'll have to do a backup and a system snapshot. Even if you never did. Do not skip it this time.
• Fully read and understand the entire instructions before you start typing. You better not have surprises along the way.
• Are you comfortable with the command line? You'll need to be.

First backup and snapshot

You decided to go ahead, so it's serious now. Grab your external HD or whatever and backup your files. Plus, install the handy system snapshot tool timeshift and create a system snapshot. Then, you're safe to begin messing with your installation.

    # These commands only do the snapshot, not the backup
    # Do the backup your way
    sudo apt install timeshift
    sudo timeshift --create
  

Switch display manager and desktop environment to LightDM and Cinnamon

Although it sounds straightforward, there are some catches:

1. It's not enough to install and configure Cinnamon. You must convince Mint Upgrade Tool you did by tricking with the packages - specially mint-meta-debian-cinnamon.
2. The way to trick the upgrader to accept you have Cinnamon in the original article breaks apt dependencies management before you finish - so you can't finish. Luckily, some commenters found the way out.
3. You better get used to LightDM and Cinnamon before ultimately switching. Specially if you share the computer with your family, like me.

Here's how I managed to do it:

Display Manager

Install LightDM packages and remove MDM ones. This requires a later reconfiguring and a reboot.

    sudo apt install lightdm
    # The removal below requires a later fixup
    sudo apt remove mdm mint-mdm-themes*
    # The fixup
    sudo dpkg-reconfigure lightdm
    # My system didn't get fully convinced till I rebooted
    sudo reboot
  

Desktop environment

This was the hardest part. The original instructions tell you to force remove some Mate packages and install the Cinnamon ones. But the force removal breaks dependencies, and apt won't install anything afterwards. But, in the order below, it works.

    sudo apt install cinnamon
    # This is when you can pause for some days
    # till you and your family get OK with Cinnamon

    # This metapackage is what tells the upgrader you have Cinnamon
    sudo apt install mint-meta-debian-cinnamon
    # The force removals below would break apt,
    # but the metapackage above saves the day
    sudo dpkg -r --force-depends mint-info-debian-mate
    sudo dpkg -r --force-depends mint-user-guide-mate
    # With Mate packages out of the way, you can finish Cinnamon install
    sudo apt install mint-info-debian-cinnamon mint-user-guide-cinnamon
  

Another backup and snapshot

This is the last safe state for your system before upgrading. Update your backup and do another snapshot. In fact, you might not need the first one anymore. But this one is crucial.

    # Again: these commands only do the snapshot, not the backup
    # Do the backup your way
    sudo timeshift --create

    # Since you're OK with the current state,
    # you can list snapshots and then erase the previous one
    sudo timeshift --list
    ...

    Num     Name                 Tags  Description
    ----------------------------------------------
    0    >  <Name>                O

    # Be sure to choose the right one!
    sudo timeshift --delete  --snapshot '<Name>'
  

In case of fire, timeshift --help is your friend.

Preparing for the upgrade

First, set your terminal to unlimited scrolling. In terminal's "Edit" menu, go to "Profile Preferences" -> "Scrolling" - "unlimited". You might need a lot of shell logging.

Preparing to upgrade means to fully update your current LMDE version, then install the upgrader, run its checks and download packages.

    sudo apt update
    sudo apt upgrade
    sudo apt install mintupgrade
    # Read the help (always!)
    mintupgrade help
    # Repeat check below until fully satisfied
    # Do not do anything else before passing absolutely all checks!
    mintupgrade check
    # Again, rinse and repeat until absolutely sure you downloaded everything
    # Don't allow any pendencies when proceeding.
    mintupgrade download
  

The upgrade

Well, you might have guessed it:

    mintupgrade upgrade
  

This command does it all. But still you have to watch: the upgrade will remove a lot of packages. Take note of them - you might want to reinstall some afterwards.

When the upgrade has finished, review overall settings. In my case, I had to reenable 'Manual login' and disable 'Hide user list' in Main Menu - Administration - Login Window - Users.

After all is done, and you are satisfied with the upgrade results, you can delete your snapshot.

    # If you want to select snapshots to remove
    sudo timeshift --list
    timeshift --delete  --snapshot '<Name>'
    # If you want to remove all snapshots
    timeshift --delete-all
  

Happy new LMDE!