🟠 High   ⏱ 15–60 min  Last verified: 25 May 2026
Affected versions: Ubuntu 18.04 (bionic)

📖 ~4 min read  •  Source: Ubuntu Security Notice USN-8018-3

Related CVEs: CVE-2026-0672 CVE-2025-15282 CVE-2025-12084 CVE-2026-0865 CVE-2023-27043 https://launchpad.net/bugs/2125702 CVE-2025-8194 CVE-2025-0938  +12 more

Upstream summary: USN-8018-1 fixed CVE-2025-12084, CVE-2025-15282, CVE-2026-0672,
CVE-2026-0865 for python3. This update provides the corresponding updates
for python2.7.

Original advisory details:

Denis Ledoux discovered that Python incorrectly parsed email message
headers. An attacker could possibly use this issue to inject arbitrary
headers into email messages. This issue only affected python3.6,
python3.7, python3.8, python3.9, python3.10, python3.11, python3.12,
python3.13, and p

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

python2.7 is executed by every process started from it, so a flaw here surfaces inside your applications rather than in python2.7 itself: header-parsing and request-smuggling bugs in the bundled HTTP stack, weaknesses in the runtime’s own TLS and crypto code, unsafe archive, XML or deserialisation handling in the standard library, or memory-safety bugs in the JIT. Long-lived workers such as application servers, JVM daemons and resident node processes keep executing the old build after Ubuntu 18.04 replaces it on disk, so a patched machine stays exposed until each one is restarted. python2.7 is an interpreter or virtual machine plus its standard library, not a daemon: it runs only inside processes you start, so there is no python2.7 unit to restart — restart the applications that execute it instead.

Environment & Reproduction

Reproduction targets Ubuntu 18.04 (bionic). Confirm release and installed package:

lsb_release -a
cat /etc/os-release
dpkg -l python2.7 | tail -2
apt-cache policy python2.7
uname -r

Exercise the workload that uses python2.7 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-8018-3. Canonical security maintainers shipped fixes in the corresponding python2.7 update for Ubuntu 18.04; running an outdated build leaves the host exposed to the failure modes described in the advisory. On this release the fix typically arrives via the Ubuntu Pro ESM (esm-infra / esm-apps) channels rather than the standard archive. Correlate apt history with the journal:

grep -A2 -B2 python2.7 /var/log/apt/history.log
zgrep -A2 -B2 python2.7 /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 18.04 to capture the current state of python2.7:

dpkg -l python2.7 | tail -1                  # installed version
dpkg -V python2.7                             # 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 python2.7 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 python2.7 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 -- 'python2.7'  # fuzzy name match; -F is required because package names contain regex metacharacters ('+' in libstdc++6/g++-13 makes -E fail to match at all)

On bionic the standard archive no longer ships security fixes. Verify Ubuntu Pro ESM coverage:

# Ubuntu Pro CLI is the standard tool:
sudo pro status --format=json 2>/dev/null | head
apt-cache policy | grep -i esm

Step-by-Step Diagnosis

  1. List failing services.

    systemctl --failed --no-pager

  2. Tail the journal / syslog for python2.7.

    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.python2.7 or usr.sbin.python2.7 — inspect first
sudo aa-complain /etc/apparmor.d/usr.bin.python2.7 2>/dev/null || true

  5. Verify python2.7 integrity and reinstall if anything is altered.

    sudo dpkg -V python2.7
sudo debsums -c python2.7 2>/dev/null
sudo apt install --reinstall -y python2.7

  6. Correlate findings with /var/log/apt/history.log, /var/log/dpkg.log, and Ubuntu Security Notice USN-8018-3 to pin the change that introduced the regression.

Solution – Primary Fix

Apply the corrective apt transaction referenced by Ubuntu Security Notice USN-8018-3, then reload the affected service:

sudo apt update
sudo apt -y install --only-upgrade python2.7
sudo systemctl daemon-reload
# Service name may differ from pkg name; check first:
dpkg -l python2.7 | tail -1            # confirm new version

On bionic the standard archive is past EoL for security; enable Ubuntu Pro ESM to receive the fix:

# Standard pro CLI:
sudo pro attach <token>
sudo pro enable esm-infra
sudo pro enable esm-apps
sudo apt update
sudo apt -y install --only-upgrade python2.7

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 python2.7
apt-mark showhold | grep python2.7
# Release the hold later with:
sudo apt-mark unhold python2.7

  • Pin a known-good version via apt preferences:

    # /etc/apt/preferences.d/python2.7.pref
Package: python2.7
Pin: version <good-version>
Pin-Priority: 1001

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

    apt-cache madison python2.7
sudo apt install --allow-downgrades -y python2.7=<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.python2.7 2>/dev/null
# reproduce the failure
sudo journalctl -k | grep apparmor | tail
sudo aa-enforce /etc/apparmor.d/usr.bin.python2.7 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 bionic-security python2.7

Verification & Acceptance Criteria

All of these should pass after the fix is applied:

dpkg -l python2.7 | 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 python2.7 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-python2-7
# LVM-on-root:
sudo lvcreate -L 4G -s -n root_pre_patch /dev/<vg>/<root-lv>

To revert:

sudo apt install --allow-downgrades -y python2.7=<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-python2-7

Prevention & Hardening

Reduce the chance of this recurring on Ubuntu 18.04 (bionic):

  • 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 for ESM (mandatory on this past-EoL release) and Livepatch where supported:

    sudo pro attach <token>
sudo pro enable esm-infra
sudo pro enable esm-apps
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 python2.7 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-18-04 tutorials on the Tutorials Hub →

Browse all common problems & solutions on the Tutorials Hub.

References & Further Reading

Primary reference: Ubuntu Security Notice USN-8018-3. Manual pages useful on Ubuntu 18.04:

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/python2.7/ for components implicated in this advisory.