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Upgrade authentik to 2026.8.1, pin init-container off debian:13-slim - #190

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nickvigilante merged 2 commits into
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authentik-2026.8.1
Sep 4, 2026
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Upgrade authentik to 2026.8.1, pin init-container off debian:13-slim#190
nickvigilante merged 2 commits into
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authentik-2026.8.1

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Summary

Upgrades authentik from 2026.2.2 to 2026.8.1 (already applied live via helm upgrade), and codifies a fix for a postgres init-container image that reproducibly failed to pull during the upgrade.

Changes

  • Chart authentik/authentik 2026.2.2 -> 2026.8.1, stepped through 2026.5.6 in between. Authentik enforces sequential major.minor upgrades -- jumping straight from 2026.2.x to 2026.8.x crash-loops the server with Major version skips are not allowed.
  • Bundled postgres's volumePermissions init container redirected from the chart default (docker.io/debian:13-slim) to docker.io/library/postgres:17.11-bookworm (already pulled for the main container, and Debian-based so it has the chown/chmod the init step needs).

Why the image override

debian:13-slim reproducibly failed to pull from gandalf twice during this upgrade with insufficient_scope: authorization failed -- confirmed it wasn't a Docker Hub rate limit (99/100 remaining via a direct token check) and no other docker.io image pulled that day hit the same error. Left unfixed, this would break any future postgres pod recreation too (node reboot, eviction, etc.), not just this one upgrade -- worth fixing durably rather than working around it once.

Testing

  • Reviewed authentik's 2026.5 and 2026.8 release notes for breaking changes affecting this cluster: AUTHENTIK_LISTEN__TRUSTED_PROXY_CIDRS already covers Traefik's pod CIDR for 2026.8's new trusted-proxy header restriction; the removed flow-import API endpoint and the hash_password CLI arg change aren't used anywhere in this repo; bundled postgres moved 17.9-bookworm -> 17.11-bookworm (patch-only, same major).
  • Live-verified post-upgrade: all three authentik pods (server/worker/postgres) healthy, /-/health/ready/ returns 200, OIDC login redirect to authentik.vigihome.net works, forward-auth-gated prometheus.vigihome.net and grafana.vigihome.net both correctly 302 through Authentik.
  • Hit and recovered from two live incidents during this upgrade (both rolled back and root-caused before retrying): the debian:13-slim pull failure, and the major-version-skip crash loop from an initial attempt that went straight from 2026.2.2 to 2026.8.1.

🤖 Built with AI assistance.

Chart 2026.2.2 -> 2026.8.1, stepped through 2026.5.6 in between --
authentik enforces sequential major.minor upgrades and jumping
straight to 2026.8.1 crash-loops the server with "Major version
skips are not allowed".

Also redirects the bundled postgres's volumePermissions init
container from the chart's default docker.io/debian:13-slim to
docker.io/library/postgres:17.11-bookworm (already pulled for the
main container). debian:13-slim reproducibly failed to pull from
gandalf twice during this upgrade with "insufficient_scope:
authorization failed" -- not a rate limit, not seen on any other
image pulled that day. Left unresolved this would break any future
postgres pod recreation (node reboot, eviction, etc.), not just
this upgrade.

Reviewed the 2026.5 and 2026.8 release notes for breaking changes:
AUTHENTIK_LISTEN__TRUSTED_PROXY_CIDRS already covers Traefik's pod
CIDR for 2026.8's new trusted-proxy header restriction; the removed
flow-import API and hash_password CLI arg change aren't used
anywhere in this repo. Verified post-upgrade: OIDC login redirect
and forward-auth-gated Prometheus/Alertmanager both working.

Assisted-by: AI
@nickvigilante
nickvigilante merged commit 9a57e8e into main Sep 4, 2026
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@nickvigilante
nickvigilante deleted the authentik-2026.8.1 branch September 4, 2026 03:42
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