🟡 Medium   ⏱ 10–30 min  Last verified: 25 May 2026
Affected versions: Ubuntu 20.04 (focal)

📖 ~4 min read  •  Source: Ubuntu Security Notice USN-8087-3

Related CVEs: CVE-2026-26007 CVE-2023-50782 CVE-2024-26130 CVE-2023-23931 CVE-2023-49083 CVE-2020-25659

Upstream summary: USN-8087-1 fixed a vulnerability in python-cryptography. This update
provides the corresponding update to Ubuntu 16.04 LTS, Ubuntu 18.04 LTS,
and Ubuntu 20.04 LTS.

Original advisory details:

It was discovered that python-cryptography incorrectly handled subgroup
validation for SECT curves. A remote attacker could use this issue to
perform a subgroup attack and possibly recover the least significant bits
of private keys.

Table of contents
  1. Symptom & Impact
  2. Environment & Reproduction
  3. Root Cause Analysis
  4. Quick Triage
  5. Step-by-Step Diagnosis
  6. Solution – Primary Fix
  7. Solution – Alternative Approaches
  8. Verification & Acceptance Criteria
  9. Rollback Plan
  10. Prevention & Hardening
  11. Related Errors & Cross-Refs
  12. References & Further Reading

Symptom & Impact

Nothing executes python-cryptography on its own; its code runs inside whatever links against or imports it, so the exposed surface on an Ubuntu 20.04 host is the union of every process that has loaded it — web workers, cron jobs, mail handlers, backup agents. The package manager replaces the files on disk, but processes already running keep the old build mapped, and virtualenvs, vendored copies and container images each carry their own copy, so a host can report itself patched while still running vulnerable code. python-cryptography is a library — code loaded by other programs rather than a daemon — so there is no unit to restart and systemctl status python-cryptography will simply report no such unit; restart its consumers instead.

Environment & Reproduction

Reproduction targets Ubuntu 20.04 (focal). Confirm release and installed package:

lsb_release -a
cat /etc/os-release
dpkg -l python-cryptography | tail -2
apt-cache policy python-cryptography
uname -r

Exercise the workload that uses python-cryptography while collecting:

needrestart -b -r l  # (pkg: needrestart) run as root; machine-readable. NEEDRESTART-SVC = units still mapping deleted libs, NEEDRESTART-SESS = login sessions, NEEDRESTART-KSTA = kernel state. -r l never restarts anything
needrestart -v -l -r l  # human-readable, libraries only (-l); names each PID and the obsolete file it still maps
checkrestart -v  # (pkg: debian-goodies) older alternative; add -p to report only deleted files owned by a dpkg package, -m for machine-readable
sudo journalctl -xe --no-pager | tail -200
sudo tail -200 /var/log/apt/history.log
sudo tail -200 /var/log/kern.log | grep -i apparmor

Root Cause Analysis

Root cause is documented in Ubuntu Security Notice USN-8087-3. Canonical security maintainers shipped fixes in the corresponding python-cryptography update for Ubuntu 20.04; running an outdated build leaves the host exposed to the failure modes described in the advisory. Fixes land in the focal-security pocket of the main archive. Correlate apt history with the journal:

grep -A2 -B2 python-cryptography /var/log/apt/history.log
zgrep -A2 -B2 python-cryptography /var/log/apt/history.log.*.gz 2>/dev/null
cat /proc/sys/kernel/tainted   # non-zero = tainted kernel / out-of-tree modules

Quick Triage

Run these on Ubuntu 20.04 to capture the current state of python-cryptography:

dpkg -l python-cryptography | tail -1                  # installed version
dpkg -V python-cryptography                             # verify shipped files
sudo apt update && apt list --upgradable 2>/dev/null | grep -i security
systemctl daemon-reload  # only if the upgrade shipped changed unit files
systemctl daemon-reexec  # REQUIRED after a systemd / libsystemd upgrade: re-execs PID 1 against the new library without rebooting (needrestart flags this as 'systemd-manager')
needrestart -r i  # (pkg: needrestart) interactive: prompts per service. The safe default on a production box
needrestart -r a  # non-interactive: restarts EVERY flagged unit. Maintenance window only -- it will bounce databases and web servers without asking
sudo ufw status verbose 2>/dev/null | head -20
sudo aa-status 2>/dev/null | head -20
# If python-cryptography ships a service unit (unit/job name often differs from pkg name, e.g.
# bind9→named, apache2→apache2, postgresql-NN→postgresql@NN-main):
dpkg-query -L python-cryptography 2>/dev/null | grep -E '^/etc/init\.d/[^/]+$'  # legacy SysV init script; its basename is the service name for 'service <name> restart' on non-systemd hosts
systemctl list-unit-files --no-pager --type=service,socket,timer | grep -iF -- 'python-cryptography'  # fuzzy name match; -F is required because package names contain regex metacharacters ('+' in libstdc++6/g++-13 makes -E fail to match at all)

Step-by-Step Diagnosis

  1. List failing services.

    systemctl --failed --no-pager

  2. Tail the journal / syslog for python-cryptography.

    sudo journalctl -xe -f --no-pager

  3. Inspect UFW (Uncomplicated Firewall) state.

    sudo ufw status numbered
sudo ufw show added
sudo iptables -L -n -v | head -30

  4. Surface AppArmor denials and switch the profile to complain mode if needed.

    sudo journalctl -k 2>/dev/null | grep -i 'apparmor="DENIED"' | tail -30
sudo aa-status
# /etc/apparmor.d/usr.bin.python-cryptography or usr.sbin.python-cryptography — inspect first
sudo aa-complain /etc/apparmor.d/usr.bin.python-cryptography 2>/dev/null || true

  5. Verify python-cryptography integrity and reinstall if anything is altered.

    sudo dpkg -V python-cryptography
sudo debsums -c python-cryptography 2>/dev/null
sudo apt install --reinstall -y python-cryptography

  6. Correlate findings with /var/log/apt/history.log, /var/log/dpkg.log, and Ubuntu Security Notice USN-8087-3 to pin the change that introduced the regression.

Solution – Primary Fix

Apply the corrective apt transaction referenced by Ubuntu Security Notice USN-8087-3, then reload the affected service:

sudo apt update
sudo apt -y install --only-upgrade python-cryptography
sudo systemctl daemon-reload
# Service name may differ from pkg name; check first:
dpkg -l python-cryptography | tail -1            # confirm new version

For kernel / glibc / systemd / openssl advisories a reboot (or Livepatch) is required:

sudo apt install -y needrestart
sudo needrestart -r l       # list units that need restart
sudo systemctl reboot       # or: sudo shutdown -r now
# Livepatch (Ubuntu Pro) avoids reboot for many kernel CVEs:
sudo canonical-livepatch status
sudo canonical-livepatch refresh

Need help rolling this patch across an Ubuntu fleet? Our IT Solutions & Services team manages Ubuntu patch windows with Landscape and Ubuntu Pro integration. Get in touch for a free consultation.

Solution – Alternative Approaches

If the primary upgrade is not viable, pick from these:

  • Hold the package so apt cannot upgrade it:

    sudo apt-mark hold python-cryptography
apt-mark showhold | grep python-cryptography
# Release the hold later with:
sudo apt-mark unhold python-cryptography

  • Pin a known-good version via apt preferences:

    # /etc/apt/preferences.d/python-cryptography.pref
Package: python-cryptography
Pin: version <good-version>
Pin-Priority: 1001

  • Downgrade to an older version if a regression is suspected:

    apt-cache madison python-cryptography
sudo apt install --allow-downgrades -y python-cryptography=<older-version>

  • Investigate AppArmor blocking the new binary; switch to complain briefly, capture denials, then re-enforce:

    sudo aa-complain /etc/apparmor.d/usr.bin.python-cryptography 2>/dev/null
# reproduce the failure
sudo journalctl -k | grep apparmor | tail
sudo aa-enforce /etc/apparmor.d/usr.bin.python-cryptography 2>/dev/null

  • Apply Canonical Livepatch (Ubuntu Pro) to land kernel fixes without reboot:

    sudo canonical-livepatch status
sudo canonical-livepatch refresh

  • Take only the security pocket update and defer the full point-release upgrade:

    sudo apt -y install --only-upgrade -t focal-security python-cryptography

Verification & Acceptance Criteria

All of these should pass after the fix is applied:

dpkg -l python-cryptography | tail -1                                  # expected fixed version
apt list --upgradable 2>/dev/null | grep -i security || echo OK
sudo ufw status numbered | head
sudo aa-status 2>/dev/null | head -5

The conditions described in the advisory must no longer be reported for python-cryptography across two consecutive runs.

Rollback Plan

Capture state before any change:

apt list --installed 2>/dev/null > /root/apt-pre.txt
dpkg --get-selections > /root/dpkg-pre.txt
# ZFS-on-root (Ubuntu 20.04+ default installer option):
sudo zfs snapshot rpool/ROOT/ubuntu@pre-python-cryptography
# LVM-on-root:
sudo lvcreate -L 4G -s -n root_pre_patch /dev/<vg>/<root-lv>

To revert:

sudo apt install --allow-downgrades -y python-cryptography=<old-version>
sudo systemctl daemon-reload
# Kernel rollback: pick the prior kernel from the GRUB menu, then:
sudo systemctl reboot
# ZFS rollback (rolls the whole root dataset):
sudo zfs rollback -r rpool/ROOT/ubuntu@pre-python-cryptography

Prevention & Hardening

Reduce the chance of this recurring on Ubuntu 20.04 (focal):

  • Enable scheduled security updates via unattended-upgrades:

    sudo apt install -y unattended-upgrades update-notifier-common
sudo dpkg-reconfigure -plow unattended-upgrades
# /etc/apt/apt.conf.d/50unattended-upgrades:
Unattended-Upgrade::Allowed-Origins { "${distro_id}:${distro_codename}-security"; };

  • Install needrestart so services restart automatically after library upgrades:

    sudo apt install -y needrestart
# /etc/needrestart/needrestart.conf -> $nrconf{restart} = 'a';

  • Attach Ubuntu Pro to enable Livepatch and extended security coverage:

    sudo pro attach <token>
sudo pro enable livepatch

  • Subscribe to ubuntu-security-announce and watch ubuntu.com/security/cves.

  • Monitor file integrity with debsums and AIDE:

    sudo apt install -y debsums aide
sudo debsums -ca
sudo aideinit && sudo mv /var/lib/aide/aide.db.new /var/lib/aide/aide.db
sudo aide --check

  • For estate-wide patching, manage with Canonical Landscape:

    sudo apt install -y landscape-client
sudo landscape-config

  • Keep AppArmor profiles in enforce mode and apply CIS Ubuntu Linux Benchmark hardening.

Issues that commonly surface alongside a python-cryptography update: apt lock contention, broken dpkg state, systemd ordering cycles, AppArmor denials, and UFW rule drift. Useful triage:

sudo dpkg --configure -a
sudo apt --fix-broken install
systemd-analyze critical-chain
sudo journalctl -k 2>/dev/null | grep -i apparmor | tail
cat /proc/sys/kernel/tainted

View all ubuntu-20-04 tutorials on the Tutorials Hub →

Browse all common problems & solutions on the Tutorials Hub.

References & Further Reading

Primary reference: Ubuntu Security Notice USN-8087-3. Manual pages useful on Ubuntu 20.04:

man apt
man apt-get
man apt-mark
man dpkg
man systemctl
man journalctl
man ufw
man apparmor
man aa-status
man unattended-upgrades
man canonical-livepatch
man pro

Other resources: Ubuntu Security Notices, Ubuntu CVE Tracker, Ubuntu upgrade notes, and per-package notes in /usr/share/doc/python-cryptography/ for components implicated in this advisory.