[Installation] Buster to Bookworm Upgrade issue

[lidfill]

Hello,

Been running Debian Buster for a while, decided to upgrade to Bookworm, basically what I did to attempt this was change the name "buster" to "bookworm" in /etc/apt/source.list, then run apt clean, apt autoclean, apt update, apt full-upgrade.

Doing this resulted in errors about missing dependencies, I tried to fix them but nothing worked, got frustrated and rebooted... now locked out, system doesn't work, pretty much shows login prompt with username, put in username and doesn't prompt password just prompts "login incorrect".

So have chrooted in and pretty much at same spot after attempting the upgrade, unsure really where to go from here, have tried apt --fix-broken install same issue, any help is very much apricated.

Code: Select all

root@debian:/# cat /etc/apt/sources.list 
deb http://deb.debian.org/debian/ bookworm main contrib non-free 
deb-src http://deb.debian.org/debian/ bookworm main contrib non-free 
deb http://security.debian.org/debian-security bookworm-security main contrib 
deb-src http://security.debian.org/debian-security bookworm-security main contrib 
deb http://deb.debian.org/debian/ bookworm-updates main contrib 
deb-src http://deb.debian.org/debian/ bookworm-updates main contrib 

root@debian:/# apt clean 

root@debian:/# apt autoclean 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 

root@debian:/# apt update 
Hit:1 http://deb.debian.org/debian bookworm InRelease 
Hit:2 http://security.debian.org/debian-security bookworm-security InRelease 
Hit:3 http://deb.debian.org/debian bookworm-updates InRelease          
Hit:4 https://dl.google.com/linux/chrome/deb stable InRelease 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
852 packages can be upgraded. Run 'apt list --upgradable' to see them. 

root@debian:/# apt upgrade 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt full-upgrade 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt --fix-broken install 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
Correcting dependencies... failed. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Error, pkgProblemResolver::Resolve generated breaks, this may be caused by held packages. 
E: Unable to correct dependencies 

root@debian:/# apt -f install 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
Correcting dependencies... failed. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Error, pkgProblemResolver::Resolve generated breaks, this may be caused by held packages. 
E: Unable to correct dependencies 

[CwF]

Step it through the releases in order, don't skip.

Buster fully updated > Bullseye (test & fix stuff) > bookworm

[Northpoint]

I have done about 10 of these upgrades just recently and I can echo what @CwF says. You upgrade buster to bullseye and then bullseye to bookworm.

I have found that going from buster to bullseye you will run into missing packages. If I remember correctly, This is because some packages have changed or the dependencies have changed. Something like that. Also, Right after I upgraded to bullseye I got the blank screen and had to <control> <alt> F (whatever- 1,2,3,4) to get to a login screen. Then login and do an update and upgrade. Ran into the "Held Back packages" also. However, The upgrade from bullseye to bookworm went without a hitch.

[Aki]

Step it through the releases in order, don't skip.

Buster fully updated > Bullseye (test & fix stuff) > bookworm

Following up on @CwF's suggestion, it might be useful to specify to follow the release notes for bullseye and bookworm (the instruction on how upgrade from buster to bullseye and then from bullseye to bookworm):

• https://www.debian.org/releases/bullseye/releasenotes

• https://www.debian.org/releases/stable/releasenotes

[Head_on_a_Stick]

It would probably work if you followed the recommendation:

Code: Select all

apt update
apt upgrade
apt full-upgrade

Stepping through releases is also recommended but I reckon APT can handle the skip as long as you don't call `full-upgrade` immediately.

If anything's going to stop it working it will be the Google Chrome repository so remember to remove Chrome and the repository before trying again. You can always replace it later.

[lidfill]

Yeah... I think I made everything worse.

Sum it up, changed source list back to Buster, tried apt clean, upgrade, it prompted to remove the broken packages (While researching my issue I read to just remove the problematic packages then upgrade), so I typed, Yes blah blah, and now I dunno... Will be googling but thought post in here since im lost and need this back online.

I tried the answer from https://unix.stackexchange.com/question ... h-variable, can check off solution 1 and 2.

Code: Select all

root@debian:/# cat /etc/apt/sources.list 

deb http://deb.debian.org/debian/ bookworm main contrib non-free 
deb-src http://deb.debian.org/debian/ bookworm main contrib non-free 

deb http://security.debian.org/debian-security bookworm-security main contrib 
deb-src http://security.debian.org/debian-security bookworm-security main contrib 

deb http://deb.debian.org/debian/ bookworm-updates main contrib 
deb-src http://deb.debian.org/debian/ bookworm-updates main contrib 

root@debian:/# apt clean 

root@debian:/# apt autoclean 

Reading package lists... Done 
Building dependency tree        
Reading state information... Done 

root@debian:/# apt update 

Hit:1 http://deb.debian.org/debian bookworm InRelease 
Hit:2 http://security.debian.org/debian-security bookworm-security InRelease 
Hit:3 http://deb.debian.org/debian bookworm-updates InRelease          
Hit:4 https://dl.google.com/linux/chrome/deb stable InRelease 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
852 packages can be upgraded. Run 'apt list --upgradable' to see them. 

root@debian:/# apt upgrade 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt full-upgrade 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt --fix-broken install 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
Correcting dependencies... failed. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Error, pkgProblemResolver::Resolve generated breaks, this may be caused by held packages. 
E: Unable to correct dependencies 

root@debian:/# apt -f install 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
Correcting dependencies... failed. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Error, pkgProblemResolver::Resolve generated breaks, this may be caused by held packages. 
E: Unable to correct dependencies 

root@debian:/# nano /etc/apt/sources.list 

root@debian:/# apt clean 

root@debian:/# apt autoclean 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 

root@debian:/# apt update 

Get:1 http://security.debian.org/debian-security buster/updates InRelease [34.8 kB] 
Hit:2 http://deb.debian.org/debian buster InRelease   
Hit:3 http://deb.debian.org/debian buster-updates InRelease 
Hit:4 https://dl.google.com/linux/chrome/deb stable InRelease 
Get:5 http://security.debian.org/debian-security buster/updates/main Sources [423 kB] 
Get:6 http://security.debian.org/debian-security buster/updates/main amd64 Packages [546 kB] 
Get:7 http://security.debian.org/debian-security buster/updates/main Translation-en [295 kB] 
Fetched 1299 kB in 2s (659 kB/s)                              
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
All packages are up to date. 

root@debian:/# apt upgrade 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
libc-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is installed 
libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is installed 
locales : Depends: libc-bin (> 2.36) but 2.28-10+deb10u2 is installed 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt --fix-broken install 

Reading package lists... Done 

Building dependency tree        

Reading state information... Done 

Correcting dependencies... Done 

The following packages were automatically installed and are no longer required: 

  dh-python libjte1 linux-image-4.19.0-24-amd64 linux-libc-dev ncurses-term openssh-sftp-server python-pip-whl python3-entrypoints python3-jaraco.classes python3-jeepney python3-keyring python3-keyrings.alt 

  python3-more-itertools python3-pycryptodome python3-secretstorage 

Use 'sudo apt autoremove' to remove them. 

The following packages will be REMOVED: 

  build-essential g++ g++-8 libc-bin libc-dev-bin libc6-dev libexpat1-dev libpython3-dev libpython3.7-dev libstdc++-8-dev locales python3-dev python3.7-dev task-english task-ssh-server 

WARNING: The following essential packages will be removed. 

This should NOT be done unless you know exactly what you are doing! 

  libc-bin 

0 upgraded, 0 newly installed, 15 to remove and 0 not upgraded. 

2 not fully installed or removed. 

After this operation, 169 MB disk space will be freed. 

You are about to do something potentially harmful. 

To continue type in the phrase 'Yes, do as I say!' 

?] Yes, do as I say! 

/usr/bin/perl: error while loading shared libraries: libcrypt.so.1: cannot open shared object file: No such file or directory 

E: Can not write log (Is /dev/pts mounted?) - posix_openpt (19: No such device) 
(Reading database ... 125496 files and directories currently installed.) 
Removing task-english (3.73) … 
Removing locales (2.36-9+deb12u1) … 
Removing python3-dev (3.7.3-1) … 
Removing python3.7-dev (3.7.3-2+deb10u5) … 
Removing libpython3-dev:amd64 (3.7.3-1) … 
Removing libpython3.7-dev:amd64 (3.7.3-2+deb10u5) … 
Removing libexpat1-dev:amd64 (2.5.0-1) … 
Removing build-essential (12.6) … 
Removing g++ (4:8.3.0-1) … 
Removing g++-8 (8.3.0-6) … 
Removing libstdc++-8-dev:amd64 (8.3.0-6) … 
Removing libc6-dev:amd64 (2.28-10+deb10u2) … 
Removing libc-dev-bin (2.28-10+deb10u2) … 
dpkg: warning: overriding problem because --force enabled: 
dpkg: warning: this is an essential package; it should not be removed 
Removing libc-bin (2.28-10+deb10u2) … 
dpkg: warning: 'ldconfig' not found in PATH or not executable 
dpkg: error: 1 expected program not found in PATH or not executable 
Note: root's PATH should usually contain /usr/local/sbin, /usr/sbin and /sbin 
E: Sub-process /usr/bin/dpkg returned an error code (2) 

root@debian:/# apt update 

Hit:1 http://deb.debian.org/debian buster InRelease 
Hit:2 http://deb.debian.org/debian buster-updates InRelease 
Hit:3 http://security.debian.org/debian-security buster/updates InRelease 
Hit:4 https://dl.google.com/linux/chrome/deb stable InRelease 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
All packages are up to date. 

root@debian:/# apt upgrade 

Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt --fix-broken install 

Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
Correcting dependencies... Done 
The following packages were automatically installed and are no longer required: 

dh-python libjte1 linux-image-4.19.0-24-amd64 linux-libc-dev ncurses-term openssh-sftp-server python-pip-whl python3-entrypoints python3-jaraco.classes python3-jeepney python3-keyring python3-keyrings.alt 

python3-more-itertools python3-pycryptodome python3-secretstorage 

Use 'sudo apt autoremove' to remove them. 

The following packages will be REMOVED: 

task-ssh-server 

0 upgraded, 0 newly installed, 1 to remove and 0 not upgraded. 

1 not fully installed or removed. 

After this operation, 6144 B disk space will be freed. 

Do you want to continue? [Y/n] Y 

/usr/bin/perl: error while loading shared libraries: libcrypt.so.1: cannot open shared object file: No such file or directory 

E: Can not write log (Is /dev/pts mounted?) - posix_openpt (19: No such device) 
dpkg: warning: 'ldconfig' not found in PATH or not executable 
dpkg: error: 1 expected program not found in PATH or not executable 
Note: root's PATH should usually contain /usr/local/sbin, /usr/sbin and /sbin 
E: Sub-process /usr/bin/dpkg returned an error code (2) 

root@debian:/# apt autoremove 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt --fix-broken install 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
Correcting dependencies... Done 
The following packages were automatically installed and are no longer required: 

dh-python libjte1 linux-image-4.19.0-24-amd64 linux-libc-dev ncurses-term openssh-sftp-server python-pip-whl python3-entrypoints python3-jaraco.classes python3-jeepney python3-keyring python3-keyrings.alt 

python3-more-itertools python3-pycryptodome python3-secretstorage 

Use 'sudo apt autoremove' to remove them. 

The following packages will be REMOVED: 

task-ssh-server 

0 upgraded, 0 newly installed, 1 to remove and 0 not upgraded. 

1 not fully installed or removed. 

After this operation, 6144 B disk space will be freed. 

Do you want to continue? [Y/n] Y 

/usr/bin/perl: error while loading shared libraries: libcrypt.so.1: cannot open shared object file: No such file or directory 

E: Can not write log (Is /dev/pts mounted?) - posix_openpt (19: No such device) 

dpkg: warning: 'ldconfig' not found in PATH or not executable 

dpkg: error: 1 expected program not found in PATH or not executable 

Note: root's PATH should usually contain /usr/local/sbin, /usr/sbin and /sbin 

E: Sub-process /usr/bin/dpkg returned an error code (2) 

root@debian:/# apt install task-english, locales, python3-dev, python3.7-dev, libpython3-dev:amd64, libpython3.7-dev:amd64, libexpat1-dev:amd64, build-essential, g++, g++-8, libstdc++-8-dev:amd64, libc6-dev:amd64, libc-dev-bin 

Reading package lists... Done 

Building dependency tree        

Reading state information... Done 

E: Unable to locate package task-english, 

E: Unable to locate package locales, 

E: Unable to locate package python3-dev, 

E: Unable to locate package python3.7-dev, 

E: Couldn't find any package by glob 'python3.7-dev,' 

E: Couldn't find any package by regex 'python3.7-dev,' 

E: Unable to locate package libpython3-dev:amd64, 

E: Unable to locate package libpython3.7-dev:amd64, 

E: Couldn't find any package by glob 'libpython3.7-dev' 

E: Couldn't find any package by regex 'libpython3.7-dev' 

E: Unable to locate package libexpat1-dev:amd64, 

E: Unable to locate package build-essential, 

E: Unable to locate package g++, 

E: Couldn't find any package by regex 'g++,' 

E: Unable to locate package g++-8, 

E: Couldn't find any package by regex 'g++-8,' 

E: Unable to locate package libstdc++-8-dev:amd64, 

E: Couldn't find any package by regex 'libstdc++-8-dev' 

E: Unable to locate package libc6-dev:amd64, 

root@debian:/# apt install aptitude 

Reading package lists... Done 

Building dependency tree        

Reading state information... Done 

You might want to run 'apt --fix-broken install' to correct these. 

The following packages have unmet dependencies: 

aptitude : Depends: aptitude-common (= 0.8.11-7) but it is not going to be installed 

            Depends: libcwidget3v5 (>= 0.5.17-8) but it is not going to be installed 

            Depends: libxapian30 (>= 1.4.10~) but it is not going to be installed 

            Recommends: libparse-debianchangelog-perl but it is not going to be installed 

task-ssh-server : Depends: openssh-server but it is not going to be installed 

E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt upgrade 

Reading package lists... Done 

Building dependency tree        

Reading state information... Done 

You might want to run 'apt --fix-broken install' to correct these. 

The following packages have unmet dependencies: 

task-ssh-server : Depends: openssh-server but it is not installed 

E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt --fix-broken install 

Reading package lists... Done 

Building dependency tree        

Reading state information... Done 

Correcting dependencies... Done 

The following packages were automatically installed and are no longer required: 

  dh-python libjte1 linux-image-4.19.0-24-amd64 linux-libc-dev ncurses-term openssh-sftp-server python-pip-whl python3-entrypoints python3-jaraco.classes python3-jeepney python3-keyring python3-keyrings.alt 

  python3-more-itertools python3-pycryptodome python3-secretstorage 

Use 'sudo apt autoremove' to remove them. 

The following packages will be REMOVED: 

  task-ssh-server 

0 upgraded, 0 newly installed, 1 to remove and 0 not upgraded. 

1 not fully installed or removed. 

After this operation, 6144 B disk space will be freed. 

Do you want to continue? [Y/n] Y 

/usr/bin/perl: error while loading shared libraries: libcrypt.so.1: cannot open shared object file: No such file or directory 

E: Can not write log (Is /dev/pts mounted?) - posix_openpt (19: No such device) 

dpkg: warning: 'ldconfig' not found in PATH or not executable 

dpkg: error: 1 expected program not found in PATH or not executable 

Note: root's PATH should usually contain /usr/local/sbin, /usr/sbin and /sbin 

E: Sub-process /usr/bin/dpkg returned an error code (2) 

root@debian:/# 

EDIT

Dunno why i added commas, long day...

Code: Select all

root@debian:/# apt install task-english locales python3-dev python3.7-dev libpython3-dev:amd64 libpython3.7-dev:amd64 libexpat1-dev:amd64 build-essential g++ g++-8 libstdc++-8-dev:amd64 libc6-dev:amd64 libc-dev-bin 

Reading package lists... Done 

Building dependency tree        

Reading state information... Done 

You might want to run 'apt --fix-broken install' to correct these. 

The following packages have unmet dependencies: 

libc-dev-bin : Depends: libc6 (< 2.29) but 2.36-9+deb12u1 is to be installed 

libc6 : Breaks: locales (< 2.36) but 2.28-10+deb10u2 is to be installed 

libc6-dev : Depends: libc6 (= 2.28-10+deb10u2) but 2.36-9+deb12u1 is to be installed 

libexpat1-dev : Depends: libexpat1 (= 2.2.6-2+deb10u6) but 2.5.0-1 is to be installed 

locales : Depends: libc-bin (> 2.28) but it is not going to be installed 

task-english : Depends: tasksel (= 3.53) but 3.73 is to be installed 

task-ssh-server : Depends: openssh-server but it is not going to be installed 

E: Unmet dependencies. 

[Head_on_a_Stick]

If anything's going to stop it working it will be the Google Chrome repository so remember to remove Chrome and the repository before trying again

[lidfill]

Thank you for the advice, but somehow just by attempting an upgrade and what ever I tired to fix it, I think I have really f%^&d it....

Chrome no go, nothing wants to corporate regarding apt, is there a way to just refresh everything, uninstall and reinstall all packages its complaining about?

Code: Select all

root@debian:/# apt purge --auto-remove google-chrome-stable 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
task-ssh-server : Depends: openssh-server but it is not going to be installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# rm /etc/apt/sources.list.d/google-chrome.list* 

root@debian:/# rm -rf ~/{.cache,.config}/google-chrome 

root@debian:/# apt purge google-chrome-stable 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
task-ssh-server : Depends: openssh-server but it is not going to be installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt clean 

root@debian:/# apt update 

Hit:1 http://security.debian.org/debian-security buster/updates InRelease 
Hit:2 http://deb.debian.org/debian buster InRelease 
Hit:3 http://deb.debian.org/debian buster-updates InRelease 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
All packages are up to date. 

root@debian:/# apt upgrade 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
You might want to run 'apt --fix-broken install' to correct these. 
The following packages have unmet dependencies: 
task-ssh-server : Depends: openssh-server but it is not installed 
E: Unmet dependencies. Try 'apt --fix-broken install' with no packages (or specify a solution). 

root@debian:/# apt --fix-broken install 
Reading package lists... Done 
Building dependency tree        
Reading state information... Done 
Correcting dependencies... Done 
The following packages were automatically installed and are no longer required: 
dh-python libjte1 linux-image-4.19.0-24-amd64 linux-libc-dev ncurses-term openssh-sftp-server python-pip-whl python3-entrypoints python3-jaraco.classes python3-jeepney python3-keyring python3-keyrings.alt 
python3-more-itertools python3-pycryptodome python3-secretstorage 
Use 'sudo apt autoremove' to remove them. 
The following packages will be REMOVED: 
task-ssh-server 
0 upgraded, 0 newly installed, 1 to remove and 0 not upgraded. 
1 not fully installed or removed. 
After this operation, 6144 B disk space will be freed. 
Do you want to continue? [Y/n] Y 

/usr/bin/perl: error while loading shared libraries: libcrypt.so.1: cannot open shared object file: No such file or directory 
E: Can not write log (Is /dev/pts mounted?) - posix_openpt (19: No such device) 
dpkg: warning: 'ldconfig' not found in PATH or not executable 
dpkg: error: 1 expected program not found in PATH or not executable 
Note: root's PATH should usually contain /usr/local/sbin, /usr/sbin and /sbin 
E: Sub-process /usr/bin/dpkg returned an error code (2) 

root@debian:/# 

[Head_on_a_Stick]

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/usr/bin/perl: error while loading shared libraries: libcrypt.so.1: cannot open shared object file: No such file or directory 
E: Can not write log (Is /dev/pts mounted?) - posix_openpt (19: No such device) 
dpkg: warning: 'ldconfig' not found in PATH or not executable 
dpkg: error: 1 expected program not found in PATH or not executable 
Note: root's PATH should usually contain /usr/local/sbin, /usr/sbin and /sbin 
E: Sub-process /usr/bin/dpkg returned an error code (2)

That perl error looks worrying but the rest of the message is because you have used the wrong command to attain a root shell.

So use

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su -

Or

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sudo -i

Before running `apt`.

[lidfill]

I am chrooted in using a live debian ISO, so this may change things, I cant login to the system anymore since attempting the upgrade.

Anyway here are my results, I seem to have RW to the system so unsure if permission issue.

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root@debian:/# su - 
su: Authentication failure 

root@debian:/# su -i 
su: invalid option -- 'i' 
Try 'su --help' for more information. 

root@debian:/# su - apt update 
su: user apt does not exist 

root@debian:/# su -i apt update 
su: invalid option -- 'i' 
Try 'su --help' for more information. 

root@debian:/# sudo -i 
sudo: account validation failure, is your account locked? 

root@debian:/# 

[Head_on_a_Stick]

I am chrooted in using a live debian ISO, so this may change things

Did you use Rescue Mode? That's the easiest way to get a working shell in a broken system.

There is also arch-chroot(8), from the arch-install-scripts package, that will (bind) mount the API filesystems automagically for you. Looks like you didn't do that before running `chroot`.

[lidfill]

I tried recovery at grub boot, but every kernal selection had same result, Login prompt -> put username in -> doesnt prompt password just says "login incorrect", only way back into system is via chroot from live usb.

After botting into live debian, created rescure directory then ran: sudo mount /dev/md126 /rescure, then sudo chroot /rescue/, and this has giving me access to the filesystem.

Sorry if i am miss understanding, but i seem to have root access to the file system and these are the same errors i received prior to rebooting and needing to chroot.

[Head_on_a_Stick]

I tried recovery at grub boot

That's not the same as Rescue Mode. Please read my link.

After botting into live debian, created rescure directory then ran: sudo mount /dev/md126 /rescure, then sudo chroot /rescue/, and this has giving me access to the filesystem.

Try

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sudo chroot /rescue /bin/su -

[lidfill]

Thank you for the advice, apologies if I misunderstand, I assume running from live disk and using chroot would be the same as booting into recovery mode? its not that I cant boot into the FS its more that the packages are corrupt so the system doesn't work, I can try rescue mode though, anyway here are my results from running your chroot from the live disk.

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user@debian:~$ sudo chroot /rescue/ 

root@debian:/# exit 

exit 

user@debian:~$ sudo chroot /rescue/ /bin/su - 
su: Authentication failure 

[lidfill]

Booted into rescue mode as suggested, then ran "dhclient enp6s0" to enable networking, attempted apt update and upgrade, but unfortunally its all the same results from when I was chrooted into the system from live disk.

whoami returned root
echo $PATH contained /usr/local/sbin, /usr/sbin, /sbin

Unfortunaly now in rescure mode I dont have a gui so cant really copy paste stuff out but its all the same errors.

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/usr/bin/perl: error while loading shared libraries: libcrypt.so.1: cannot open shared object file: No such file or directory 
E: Can not write log (Is /dev/pts mounted?) - posix_openpt (19: No such device) 
dpkg: warning: 'ldconfig' not found in PATH or not executable 
dpkg: error: 1 expected program not found in PATH or not executable 
Note: root's PATH should usually contain /usr/local/sbin, /usr/sbin and /sbin 

Seems ldconfig is no longer in my system. "which ldconfig" returns nothing, running "ldconfig" alone return command not found.

"dpkg --configure -a" returns same error.

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dpkg: warning: 'ldconfig' not found in PATH or not executable 
dpkg: error: 1 expected program not found in PATH or not executable 
Note: root's PATH should usually contain /usr/local/sbin, /usr/sbin and /sbin 

Is there anyway I can reinstall ldconfig? Or am I going to have to reinstall the OS, I prefer not to...

[Hallvor]

Your install has severe issues, and attempting to fix it all is likely more time-consuming than reinstalling the OS (or preferably restore the old system from a backup device).

[ccheltenham]

Just my humble opinion, I would not skip bullseye and go from buster to bookworm.
I would restore and try to upgrade one version at a time.

However , I do have one upgrade from bullseye to bookworm that does a full uprade when I have not invoked full upgrade.

In other words , it attempts tp upgrade to trixie from bookworm and I don't want it to.
Then it gives me that sid thing which no one know wtf that means.

Basically if I simply do #apt update its clean
# apt upgrade will cite a ton of files
Its now at 260 becasue its been a while since I have been able to update the OS
However when finished it i run lsb_release -a and it says its Trixie SID.

Its a production system at my job and its very concerning.
It makes me want to go back to Red Hat that I deviated from post IBM takeover.

I guess the question is , How do I upgrade everything except the kernel.


This where I end up -
ccheltenham@jenkins-3:~$ lsb_release -a
No LSB modules are available.
Distributor ID: Debian
Description: Debian GNU/Linux trixie/sid
Release: n/a
Codename: trixie
ccheltenham@jenkins-3:~$ cat /etc/os-release
PRETTY_NAME="Debian GNU/Linux trixie/sid"
NAME="Debian GNU/Linux"
VERSION_CODENAME=trixie
ID=debian
HOME_URL="https://www.debian.org/"
SUPPORT_URL="https://www.debian.org/support"
BUG_REPORT_URL="https://bugs.debian.org/"
ccheltenham@jenkins-3:~$

Why is trixie mentioned?
I didn't do a full-upgrade and there's no mention of trixie in any of the repos.

ccheltenham@jenkins-3:~$ sudo su -
root@jenkins-3:~# cd /etc/apt
root@jenkins-3:/etc/apt# grep -ri trixe *
root@jenkins-3:/etc/apt# cd /etc/apt
root@jenkins-3:/etc/apt# ll
total 28
drwxr-xr-x 2 root root 4096 Aug 23 13:30 apt.conf.d
drwxr-xr-x 2 root root 4096 Jun 10 2021 auth.conf.d
drwxr-xr-x 2 root root 4096 Sep 11 2022 keyrings
drwxr-xr-x 2 root root 4096 Jun 10 2021 preferences.d
-rw-r--r-- 1 root root 517 Aug 22 11:14 sources.list
drwxr-xr-x 2 root root 4096 Aug 22 11:14 sources.list.d
drwxr-xr-x 2 root root 4096 Aug 23 13:20 trusted.gpg.d
root@jenkins-3:/etc/apt# grep -ri trixe *
root@jenkins-3:/etc/apt#

[Northpoint]

The carnage is real on this one. I would really just make sure you have a backup of the /etc directory and any other important stuff and just reinstall.

Normally what I do with servers is I run virtualbox for my major/important installs. Things like nextcloud or invoice and billing software. This way the host OS just handles things like dhcp/samba/network-firewall/Reverse Proxies. These are easily recreated because I backup the whole /etc directory on the host. The guest systems I will clone before I do any updates/upgrades. Therefore if things go south I can boot the clone instead. Minimal downtime.

I have one server that I have to upgrade the guest VM. Its currently running buster and I am going to take it up to bookworm. Here is the approach I have learned for the planned upgrade(s). Copied this from my notes for the bullseye to bookworm upgrade but just substitute the versions for the buster to bullseye upgrade:


Replacing bullseye with bookworm:

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sudo sed -i 's/bullseye/bookworm/g' /etc/apt/sources.list

This is for the /etc/apt/sources.list.d directory:

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sudo sed -i 's/bullseye/bookworm/g' /etc/apt/sources.list.d/*

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apt update
sudo apt upgrade --without-new-pkgs
sudo apt full-upgrade

Here I just make sure the release is correct and then do a clean up.

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lsb_release -a
sudo apt --purge autoremove
sudo apt autoclean

Just my .02 cents worth. I gleaned this from reading thru some nice websites. Most any problem I had was moving from buster to bullseye. This is due to package changes and discontinued stuff.

[lidfill]

Thanks everyone, I was unaware how important step upgrading was in Debian, silly of me I did not do a backup but I will copy off the /etc dir and any config I need, the main stuff is on a separate soft raid to the OS so I guess it should be ok reinstalling.

Thanks again everyone, least upgrade fail made me join this community haha.