I have two Ubuntu 18.04.6 LTS servers (droplets) which I can't and don't want to upgrade right now. One of them is running pip==22.2.2 and when I run this command I get this output:

pip freeze|grep -i certb
certbot==2.10.0
certbot-apache==2.10.0
certbot-dns-digitalocean==2.10.0

The other one is running pip==21.3.1 and when I run this command I get this output:

pip freeze|grep -i certb
/usr/lib/python3/dist-packages/secretstorage/dhcrypto.py:15: CryptographyDeprecationWarning: Python 3.6 is no longer supported by the Python core team. Therefore, support for it is deprecated in cryptography and will be removed in a future release.
  from cryptography.utils import int_from_bytes
certbot==1.23.0
certbot-apache==1.23.0
certbot-dns-digitalocean==1.23.0
certbot-dns-route53==1.23.0

I want to know how do I upgrade pip, certbot and optionally Python to its latest version in both machines, and especially the second machine?

I also have two machines with Ubuntu 22.04.4 LTS. There I have problems with Ubuntu pro:

# sudo pro detach
Detach will disable the following service:
    livepatch
Are you sure? (y/N) y
Executing `/snap/bin/canonical-livepatch disable`
An unexpected error occurred: Failed running command '/snap/bin/canonical-livepatch disable' [exit(1)]. Message: cannot create mount point for file "/tmp/snap.rootfs_GcwX7d/README.md": Permission denied

For more details, see the log: /var/log/ubuntu-advantage.log
If you think this is a bug, please run: ubuntu-bug ubuntu-advantage-tools
# pro status
SERVICE          ENTITLED  STATUS       DESCRIPTION
anbox-cloud      yes       disabled     Scalable Android in the cloud
esm-apps         yes       disabled     Expanded Security Maintenance for Applications
esm-infra        yes       disabled     Expanded Security Maintenance for Infrastructure
livepatch        yes       warning      Canonical Livepatch service
realtime-kernel  yes       disabled     Ubuntu kernel with PREEMPT_RT patches integrated
usg              yes       disabled     Security compliance and audit tools

NOTICES
Error running canonical-livepatch status:
cannot create mount point for file "/tmp/snap.rootfs_dUW8Xu/README.md": Permission denied


For a list of all Ubuntu Pro services, run 'pro status --all'
Enable services with: pro enable <service>

     Account: uri@speedy.net
Subscription: Ubuntu Pro - free personal subscription

I recently ran the following upgrade commands for all the above machines, and I got many times in the Ubuntu 22.04.4 LTS to select an option (I always selected the default):

sudo apt update
sudo apt upgrade
sudo apt dist-upgrade
sudo apt autoremove
sudo apt autoclean

sudo apt autoremove
sudo apt-get update
sudo apt-get upgrade
sudo apt update
sudo apt upgrade

And I also had to run the following commands:

cd /var/lib/dpkg
sudo mv info info.bak
sudo mkdir info
sudo apt-get upgrade

Thanks,

Uri Rodberg, Speedy Net