diff --git a/NEWS.md b/NEWS.md
index aed1a76e3..4fc987249 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -6,6 +6,15 @@ width: 128px;
 border-radius: 128px;
 " />
 
+## v2.2.8
+
+- Fixes
+    - Codex updates itself again, automatically or on demand, and announces new
+      versions.
+- Documentation
+    - Docs for passing through the Server: HTTP header so codex may be
+      identified by OPDS clients like Stump.
+
 ## v2.2.7
 
 - Fixes
diff --git a/README.md b/README.md
index 6b8ea1f06..8cf55e459 100644
--- a/README.md
+++ b/README.md
@@ -651,6 +651,9 @@ location ^~ /codex {
     # If the nginx credentials are different than codex credentials use this line to
     #   not forward the authorization.
     proxy_set_header   Authorization "";
+    # Let clients see "Server: codex/<version>" instead of "Server: nginx".
+    # nginx hides the upstream Server header by default. See below.
+    proxy_pass_header  Server;
 }
 ```
 
@@ -666,6 +669,37 @@ of the `/codex` location with `auth_request`, exempt the API the way Codex's own
 examples do (`location /codex/api { auth_request off; ... }`); the `^~` note
 above is what keeps the static assets reachable.
 
+#### Preserving the Codex Server Header
+
+Codex identifies itself with a `Server: codex/<version>` response header, which
+is how OPDS clients, uptime monitors and support requests tell a Codex install
+apart from whatever is proxying it. nginx does **not** pass that header through:
+by default it hides `Date`, `Server`, `X-Accel-...` and `X-Pad` from the
+upstream response and substitutes its own `Server: nginx/<version>`. Add
+[`proxy_pass_header`](https://nginx.org/en/docs/http/ngx_http_proxy_module.html#proxy_pass_header)
+to the Codex location (as in the example above) to un-hide it:
+
+```nginx
+proxy_pass_header Server;
+```
+
+```console
+$ curl -sI https://example.com/codex/ | grep -i '^server'
+server: codex/2.2.8
+```
+
+Notes:
+
+- `server_tokens off;` is not a substitute. It only shortens nginx's own header
+  to `Server: nginx`; the Codex header is still discarded.
+- Like `proxy_set_header`, `proxy_pass_header` is inherited from the enclosing
+  `http {}` / `server {}` block **only if no `proxy_pass_header` is defined in
+  the location itself**. Keep it in the same block as the rest of the Codex
+  proxy headers.
+- Other reverse proxies have their own rules for the `Server` header; if
+  `curl -sI` shows something other than `codex/<version>`, check your proxy's
+  documentation for passing upstream response headers through.
+
 #### Nginx Reverse Proxy 502 when container refreshes
 
 Nginx requires a special trick to refresh dns when linked Docker containers
diff --git a/codex/librarian/bookmark/bookmarkd.py b/codex/librarian/bookmark/bookmarkd.py
index 656349220..825314b43 100644
--- a/codex/librarian/bookmark/bookmarkd.py
+++ b/codex/librarian/bookmark/bookmarkd.py
@@ -146,7 +146,9 @@ def _process_task_immediately(self, task) -> None:
                 )
                 self._spawn_offline(
                     "latest-version",
-                    lambda: worker.update_latest_version(force=task.force),
+                    lambda: worker.update_latest_version(
+                        force=task.force, update=task.update
+                    ),
                 )
             case _:
                 self.log.warning(f"Unknown Bookmark task {task}")
diff --git a/codex/librarian/bookmark/latest_version.py b/codex/librarian/bookmark/latest_version.py
index c42d30fb9..c92991563 100644
--- a/codex/librarian/bookmark/latest_version.py
+++ b/codex/librarian/bookmark/latest_version.py
@@ -2,32 +2,96 @@
 
 import json
 from datetime import timedelta
-from typing import Final
+from threading import Lock
+from time import monotonic
+from typing import ClassVar, Final
 from urllib.request import urlopen
 
 from django.utils import timezone
 
+from codex.choices.admin import AdminFlagChoices
 from codex.librarian.scribe.janitor.status import JanitorCodexLatestVersionStatus
 from codex.librarian.scribe.janitor.tasks import JanitorCodexUpdateTask
 from codex.librarian.worker import WorkerStatusBase
-from codex.models import Timestamp
+from codex.models import AdminFlag, Timestamp
 from codex.version import PACKAGE_NAME
 
 _REPO_URL: Final = f"https://pypi.python.org/pypi/{PACKAGE_NAME}/json"
 _CACHE_EXPIRY: Final = timedelta(days=1) - timedelta(minutes=5)
 _REPO_TIMEOUT: Final = 5
+_FAILURE_BACKOFF: Final = 600.0
+
+
+class _FetchGate:
+    """
+    Process wide guard against stampeding PyPI fetches.
+
+    Every ``CodexLatestVersionTask`` builds a fresh updater on its own
+    daemon thread, so this state cannot live on the instance. While the
+    cache is empty *every* request to ``/api/v4/version`` queues a fetch
+    task, so without the lock a slow or unreachable PyPI means one
+    5 second outbound connection per request. ``next_attempt`` adds a
+    cooldown after a failure so an outage doesn't retry on every hit.
+    """
+
+    lock: ClassVar[Lock] = Lock()
+    next_attempt: ClassVar[float] = 0.0
 
 
 class CodexLatestVersionUpdater(WorkerStatusBase):
     """Methods for fetching the latest version."""
 
     @staticmethod
-    def _fetch_latest_version():
+    def _fetch_latest_version() -> str:
         """Fetch Latest Remotely."""
         response = urlopen(_REPO_URL, timeout=_REPO_TIMEOUT)
         source = response.read()
         decoded_source = source.decode("utf-8")
-        return json.loads(decoded_source)["info"]["version"]
+        latest_version = json.loads(decoded_source)["info"]["version"]
+        if not latest_version:
+            reason = "Bad latest version fetched."
+            raise ValueError(reason)
+        return latest_version
+
+    def _is_fetch_due(self, ts, *, force: bool) -> bool:
+        """Is the cached latest version stale enough to refetch."""
+        if not (
+            force or not ts.value or timezone.now() - ts.updated_at > _CACHE_EXPIRY
+        ):
+            self.log.debug("Not fetching new latest version, not expired.")
+            return False
+        if not force and monotonic() < _FetchGate.next_attempt:
+            self.log.debug("Not fetching new latest version, waiting after a failure.")
+            return False
+        return True
+
+    def _fetch_latest_version_into_cache(self, ts, *, force: bool) -> None:
+        """Fetch the latest version into the timestamp cache if it's due."""
+        if not self._is_fetch_due(ts, force=force):
+            return
+        if not _FetchGate.lock.acquire(blocking=False):
+            self.log.debug("Latest codex version fetch already in flight.")
+            return
+        try:
+            latest_version = self._fetch_latest_version()
+        except Exception:
+            _FetchGate.next_attempt = monotonic() + _FAILURE_BACKOFF
+            raise
+        finally:
+            _FetchGate.lock.release()
+        ts.value = latest_version
+        ts.save()
+        self.log.info(f"Saved new latest codex version {latest_version}.")
+
+    def _queue_update(self, ts) -> None:
+        """Chain into an update task if the admin enabled automatic updates."""
+        if not ts.value:
+            return
+        flag = AdminFlag.objects.only("on").get(key=AdminFlagChoices.AUTO_UPDATE.value)
+        if not flag.on:
+            self.log.debug("Auto update is disabled, not updating codex.")
+            return
+        self.librarian_queue.put(JanitorCodexUpdateTask())
 
     def update_latest_version(self, *, force: bool, update: bool = False) -> None:
         """Get the latest version from a remote repo using a cache."""
@@ -38,26 +102,10 @@ def update_latest_version(self, *, force: bool, update: bool = False) -> None:
         try:
             self.status_controller.start(status)
             ts = Timestamp.objects.get(key=Timestamp.Choices.CODEX_VERSION.value)
-            do_fetch = (
-                force
-                or not ts.value
-                or (timezone.now() - ts.updated_at > _CACHE_EXPIRY)
-            )
-            if do_fetch:
-                latest_version = self._fetch_latest_version()
-                if not latest_version:
-                    reason = "Bad latest version fetched."
-                    raise ValueError(reason)
-                ts.value = latest_version
-                ts.save()
-                level = "INFO"
-                log_txt = f"Saved new latest codex version {latest_version}."
-                if update:
-                    task = JanitorCodexUpdateTask()
-                    self.librarian_queue.put(task)
-            else:
-                level = "DEBUG"
-                log_txt = "Not fetching new latest version, not expired."
-            self.log.log(level, log_txt)
+            self._fetch_latest_version_into_cache(ts, force=force)
+            if update:
+                # Only after a completed fetch, so the update decision
+                # sees the version this run just learned about.
+                self._queue_update(ts)
         finally:
             self.status_controller.finish(status)
diff --git a/codex/librarian/bookmark/tasks.py b/codex/librarian/bookmark/tasks.py
index 52689abc8..4b4014c22 100644
--- a/codex/librarian/bookmark/tasks.py
+++ b/codex/librarian/bookmark/tasks.py
@@ -50,6 +50,15 @@ class ClearLibrarianStatusTask(BookmarkTask):
 
 @dataclass
 class CodexLatestVersionTask(BookmarkTask):
-    """Get the latest version."""
+    """
+    Get the latest version.
+
+    ``update`` requests that a successful fetch chain into a
+    ``JanitorCodexUpdateTask`` if the Auto Update admin flag is on.
+    Only the nightly janitor sets it. Chaining (rather than queueing
+    both tasks up front) keeps the update from racing ahead of the
+    fetch that tells it whether an update is even available.
+    """
 
     force: bool = False
+    update: bool = False
diff --git a/codex/librarian/scribe/janitor/janitor.py b/codex/librarian/scribe/janitor/janitor.py
index 9fe4c1b1f..fe0617c0a 100644
--- a/codex/librarian/scribe/janitor/janitor.py
+++ b/codex/librarian/scribe/janitor/janitor.py
@@ -86,26 +86,30 @@
     RemoveCoversStatus,
 )
 
-_NIGHTLY_TASK_CLASSES: Final[tuple[type[LibrarianTask], ...]] = (
-    CodexLatestVersionTask,
-    JanitorAdoptOrphanFoldersTask,
-    JanitorForeignKeyCheckTask,
-    JanitorFolderRelationsCheckTask,
-    JanitorIntegrityCheckTask,
-    JanitorFTSIntegrityCheckTask,
-    JanitorCleanFKsTask,
-    JanitorCleanCoversTask,
-    JanitorCleanupSessionsTask,
-    JanitorCleanupBookmarksTask,
-    JanitorCleanupSettingsTask,
-    JanitorCleanupFavoritesTask,
-    JanitorCleanupTaggingStateTask,
-    SearchIndexSyncTask,
-    SearchIndexOptimizeTask,
-    JanitorVacuumTask,
-    JanitorBackupTask,
-    JanitorDumpUserDataTask,
-    CoverRemoveOrphansTask,
+_NIGHTLY_TASKS: Final[tuple[LibrarianTask, ...]] = (
+    # Instances, not classes: the version check carries arguments. It
+    # forces a fetch (the nightly run is the daily refresh) and asks the
+    # fetcher to chain into an update task, which it does only if the
+    # Auto Update admin flag is on.
+    CodexLatestVersionTask(force=True, update=True),
+    JanitorAdoptOrphanFoldersTask(),
+    JanitorForeignKeyCheckTask(),
+    JanitorFolderRelationsCheckTask(),
+    JanitorIntegrityCheckTask(),
+    JanitorFTSIntegrityCheckTask(),
+    JanitorCleanFKsTask(),
+    JanitorCleanCoversTask(),
+    JanitorCleanupSessionsTask(),
+    JanitorCleanupBookmarksTask(),
+    JanitorCleanupSettingsTask(),
+    JanitorCleanupFavoritesTask(),
+    JanitorCleanupTaggingStateTask(),
+    SearchIndexSyncTask(),
+    SearchIndexOptimizeTask(),
+    JanitorVacuumTask(),
+    JanitorBackupTask(),
+    JanitorDumpUserDataTask(),
+    CoverRemoveOrphansTask(),
 )
 _JANITOR_METHOD_MAP: Final[MappingProxyType[type, str]] = MappingProxyType(
     {
@@ -147,8 +151,8 @@ def queue_nightly_tasks(self) -> None:
         """Queue all the janitor tasks."""
         try:
             self.status_controller.start_many(_JANITOR_STATII)
-            for task_class in _NIGHTLY_TASK_CLASSES:
-                self.librarian_queue.put(task_class())
+            for task in _NIGHTLY_TASKS:
+                self.librarian_queue.put(task)
             Timestamp.touch(Timestamp.Choices.JANITOR)
         except Exception:
             self.log.exception(f"In {self.__class__.__name__}")
diff --git a/codex/librarian/scribe/janitor/update.py b/codex/librarian/scribe/janitor/update.py
index 4fceb5f65..63f1a922c 100644
--- a/codex/librarian/scribe/janitor/update.py
+++ b/codex/librarian/scribe/janitor/update.py
@@ -2,16 +2,23 @@
 
 import subprocess
 import sys
+from importlib import invalidate_caches
+from importlib.util import find_spec
+from shutil import which
+from typing import Final
 
-from packaging.version import Version
-
-from codex.choices.admin import AdminFlagChoices
 from codex.librarian.restarter.tasks import CodexRestartTask
 from codex.librarian.scribe.janitor.cleanup import JanitorCleanup
 from codex.librarian.scribe.janitor.status import JanitorCodexUpdateStatus
-from codex.models import AdminFlag
 from codex.models.admin import Timestamp
-from codex.version import VERSION, get_version
+from codex.util import is_docker
+from codex.version import PACKAGE_NAME, VERSION, get_version, is_outdated
+
+# Long enough for a slow index and a source build, short enough that a
+# hung installer doesn't wedge the scribe thread forever. Every import,
+# search index sync and janitor job waits behind this one queue.
+_INSTALL_TIMEOUT: Final = 600
+_STDERR_TAIL: Final = 20
 
 
 class JanitorCodexUpdate(JanitorCleanup):
@@ -19,68 +26,113 @@ class JanitorCodexUpdate(JanitorCleanup):
 
     def _is_outdated(self) -> bool:
         """Is codex outdated."""
-        result = False
-        if not VERSION:
-            self.log.warning("Cannot determine installed Codex version.")
-            return result
         ts = Timestamp.objects.get(key=Timestamp.Choices.CODEX_VERSION.value)
         latest_version = ts.value
-        packaging_latest_version = Version(latest_version)
+        result = is_outdated(VERSION, latest_version)
+        self.log.debug(f"{latest_version=} > {VERSION=} = {result}")
+        return result
 
-        installed_packaging_version = Version(VERSION)
-        if (
-            packaging_latest_version.is_prerelease
-            and not installed_packaging_version.is_prerelease
-        ):
-            pre_blurb = "latest version is a prerelease. But installed version is not."
+    def _installer_args(self) -> tuple[str, ...] | None:
+        """
+        Build the upgrade command for however this codex was installed.
+
+        pip is the common case but it isn't guaranteed to exist: uv and
+        pipx environments omit it, and the Codex docker image uninstalls
+        it from the runtime layer. uv installs into an explicit
+        interpreter, so point it at this one rather than whatever it
+        would discover on its own.
+        """
+        if find_spec("pip"):
+            return (sys.executable, "-m", "pip", "install", "--upgrade", PACKAGE_NAME)
+        if uv := which("uv"):
+            return (
+                uv,
+                "pip",
+                "install",
+                "--upgrade",
+                "--python",
+                sys.executable,
+                PACKAGE_NAME,
+            )
+        reason = (
+            f"Cannot update Codex: neither pip nor uv is available to {sys.executable}."
+        )
+        if is_docker():
+            reason += " Codex is running in Docker. Pull a new image to update."
+        self.log.error(reason)
+        return None
+
+    def _run_installer(self, args: tuple[str, ...]) -> bool:
+        """Run the installer, logging its output on failure."""
+        self.log.info(f"Updating Codex with: {' '.join(args)}")
+        try:
+            subprocess.run(  # noqa: S603
+                args,
+                check=True,
+                capture_output=True,
+                text=True,
+                timeout=_INSTALL_TIMEOUT,
+            )
+        except subprocess.CalledProcessError as exc:
+            # The installer's own diagnosis is worth far more to an
+            # admin than a traceback out of subprocess.
+            output = (exc.stderr or exc.stdout or "").strip().splitlines()
+            tail = "\n".join(output[-_STDERR_TAIL:])
+            reason = f"Codex update failed with code {exc.returncode}:\n{tail}"
+        except subprocess.TimeoutExpired:
+            reason = (
+                f"Codex update timed out after {_INSTALL_TIMEOUT} seconds: {args[0]}"
+            )
         else:
-            result = packaging_latest_version > installed_packaging_version
-            pre_blurb = ""
-        self.log.debug(f"{latest_version=} > {VERSION=} = {result}{pre_blurb}")
-        return result
+            return True
+        self.log.error(reason)
+        return False
+
+    def _update_codex(self, *, force: bool) -> bool:
+        """
+        Install the latest codex if warranted. Return whether it ran.
 
-    def _update_codex(self, *, force: bool) -> None:
+        The Auto Update admin flag is *not* checked here. It gates the
+        nightly path only, at the point where the version check chains
+        into this task. An admin who pushes the Update Codex button in
+        the jobs tab is asking for an update, flag or no flag.
+        """
         if force:
             self.log.info("Forcing update of Codex.")
-        else:
-            eau = AdminFlag.objects.only("on").get(
-                key=AdminFlagChoices.AUTO_UPDATE.value
-            )
-            if not eau.on or not self._is_outdated():
-                self.log.info("Codex is up to date.")
-                return
-
+        elif self._is_outdated():
             self.log.info("Codex seems outdated. Trying to update.")
+        else:
+            self.log.info("Codex is up to date.")
+            return False
 
-        args = (
-            sys.executable,
-            "-m",
-            "pip",
-            "install",
-            "--upgrade",
-            "codex",
-        )
-        subprocess.run(  # noqa: S603
-            args,
-            check=True,
-        )
+        args = self._installer_args()
+        if not args:
+            return False
+        return self._run_installer(args)
 
     def update_codex(self, *, force: bool) -> None:
         """Update the package and restart everything if the version changed."""
         status = JanitorCodexUpdateStatus()
         try:
             self.status_controller.start(status)
-            self._update_codex(force=force)
+            installed = self._update_codex(force=force)
         except Exception:
             self.log.exception("Updating Codex software")
+            installed = False
         finally:
             self.status_controller.finish(status)
 
-        # Restart if changed version.
-        new_version = get_version()
-        restart = new_version != VERSION
+        if not installed:
+            return
 
-        if restart:
+        # Restart if changed version. importlib.metadata caches its
+        # distribution search per directory mtime, so drop the caches
+        # before reading the version the installer just wrote. A stale
+        # read here means a successful update never restarts into the
+        # new code.
+        invalidate_caches()
+        new_version = get_version()
+        if new_version != VERSION:
             self.log.success(f"Codex was updated from {VERSION} to {new_version}.")
             self.librarian_queue.put(CodexRestartTask())
         else:
diff --git a/codex/librarian/telemeter/stats.py b/codex/librarian/telemeter/stats.py
index 140df6a0a..6935c2391 100644
--- a/codex/librarian/telemeter/stats.py
+++ b/codex/librarian/telemeter/stats.py
@@ -1,7 +1,6 @@
 """Admin Flag View."""
 
 from multiprocessing import cpu_count
-from pathlib import Path
 from platform import machine, python_version, release, system
 from types import MappingProxyType
 from typing import Any, Final
@@ -29,6 +28,7 @@
     Comic,
 )
 from codex.models.settings import SettingsBrowser, SettingsReader
+from codex.util import is_docker
 from codex.version import VERSION
 from codex.views.const import (
     CONFIG_MODELS,
@@ -51,8 +51,6 @@
         "usage": STATS_USAGE_MODELS,
     }
 )
-_DOCKERENV_PATH = Path("/.dockerenv")
-_CGROUP_PATH = Path("/proc/self/cgroup")
 _USER_STATS: Final = (
     (
         SettingsBrowser,
@@ -88,14 +86,6 @@ def __init__(self, params=None) -> None:
             params = {}
         self.params = params
 
-    @classmethod
-    def _is_docker(cls) -> bool:
-        """Test if we're in a docker container."""
-        try:
-            return _DOCKERENV_PATH.is_file() or "docker" in _CGROUP_PATH.read_text()
-        except Exception:
-            return False
-
     def _get_models(self, key) -> tuple:
         """Get models from request params."""
         request_model_set = self.params.get(key, {})
@@ -173,7 +163,7 @@ def _add_platform(self, obj) -> None:
         if self.params and "platform" not in self.params:
             return
         platform = {
-            "docker": self._is_docker(),
+            "docker": is_docker(),
             "machine": machine(),
             "cores": cpu_count(),
             "system": {
diff --git a/codex/run.py b/codex/run.py
index a92786061..ac09dd0ec 100755
--- a/codex/run.py
+++ b/codex/run.py
@@ -42,11 +42,22 @@ def _database_checkpoint() -> None:
 
 
 def restart() -> None:
-    """Restart this process."""
-    from sys import argv
+    """
+    Restart this process.
+
+    Re-exec the running interpreter, not ``__file__``. Exec'ing this
+    module directly relied on its executable bit surviving the wheel and
+    on its ``#!/usr/bin/env python3`` shebang resolving to a python that
+    has codex installed. Under pipx, uv, homebrew, systemd or launchd
+    that first ``python3`` on PATH is frequently a different interpreter
+    entirely, and the restart died with ModuleNotFoundError instead of
+    coming back up. ``sys.executable`` is by definition the interpreter
+    codex is installed into.
+    """
+    from sys import argv, executable
 
     print("Restarting Codex. Hold on to your butts...", flush=True)  # noqa: T201
-    execv(__file__, argv)  # noqa: S606
+    execv(executable, (executable, "-m", "codex.run", *argv[1:]))  # noqa: S606
 
 
 def codex_shutdown() -> None:
diff --git a/codex/serializers/versions.py b/codex/serializers/versions.py
index 2c2a2b2f4..247914886 100644
--- a/codex/serializers/versions.py
+++ b/codex/serializers/versions.py
@@ -1,6 +1,6 @@
 """Versions Serializer."""
 
-from rest_framework.fields import CharField
+from rest_framework.fields import BooleanField, CharField
 from rest_framework.serializers import Serializer
 
 
@@ -9,4 +9,6 @@ class VersionsSerializer(Serializer):
 
     installed = CharField(read_only=True)
     latest = CharField(read_only=True)
+    outdated = BooleanField(read_only=True)
+    docker = BooleanField(read_only=True)
     warning = CharField(read_only=True)
diff --git a/codex/util.py b/codex/util.py
index faecd2b3e..8481d02c2 100644
--- a/codex/util.py
+++ b/codex/util.py
@@ -1,6 +1,28 @@
 """Utility functions."""
 
 from collections.abc import Mapping
+from functools import cache
+from pathlib import Path
+from typing import Final
+
+_DOCKERENV_PATH: Final = Path("/.dockerenv")
+_CGROUP_PATH: Final = Path("/proc/self/cgroup")
+
+
+@cache
+def is_docker() -> bool:
+    """
+    Is codex running inside a docker container.
+
+    Cached: a process cannot change containers, and this is consulted
+    on every version request. Containers are immutable deployments, so
+    codex updates itself by being replaced with a new image, not by
+    installing over itself.
+    """
+    try:
+        return _DOCKERENV_PATH.is_file() or "docker" in _CGROUP_PATH.read_text()
+    except Exception:
+        return False
 
 
 def max_none(*args):
diff --git a/codex/version.py b/codex/version.py
index bef11c5c8..cd6cd8c35 100644
--- a/codex/version.py
+++ b/codex/version.py
@@ -2,6 +2,8 @@
 
 from importlib.metadata import PackageNotFoundError, version
 
+from packaging.version import InvalidVersion, Version
+
 PACKAGE_NAME = "codex"
 
 
@@ -15,3 +17,26 @@ def get_version() -> str:
 
 
 VERSION = get_version()
+
+
+def is_outdated(installed: str, latest: str) -> bool:
+    """
+    Is the installed version older than the latest published version.
+
+    Pure and total: never raises. Unparseable versions mean "don't
+    know", which is reported as not outdated. That covers a source
+    checkout (``VERSION == "test"``) and an empty or garbage latest
+    version cache, both of which used to raise ``InvalidVersion`` from
+    the janitor's update check.
+    """
+    if not installed or not latest:
+        return False
+    try:
+        installed_version = Version(installed)
+        latest_version = Version(latest)
+    except InvalidVersion:
+        return False
+    if latest_version.is_prerelease and not installed_version.is_prerelease:
+        # Never auto-advance a stable install onto a prerelease.
+        return False
+    return latest_version > installed_version
diff --git a/codex/views/version.py b/codex/views/version.py
index fe1318a29..74db1849f 100644
--- a/codex/views/version.py
+++ b/codex/views/version.py
@@ -9,18 +9,25 @@
 from codex.models import Timestamp
 from codex.serializers.versions import VersionsSerializer
 from codex.settings import DOCKER_IMAGE_DEPRECATED
-from codex.version import VERSION
+from codex.util import is_docker
+from codex.version import VERSION, is_outdated
 from codex.views.auth import AuthGenericAPIView
 
 
-def version_payload() -> dict[str, str]:
+def version_payload() -> dict[str, str | bool]:
     """
-    Build the ``{installed, latest, warning}`` version dict.
+    Build the ``{installed, latest, outdated, docker, warning}`` version dict.
 
     Shared by :class:`VersionView` and the composite
     :class:`~codex.views.session.SessionView` so the two endpoints
     can't drift. Kicks off a latest-version fetch task when the cached
     ``Timestamp`` row is still empty.
+
+    ``outdated`` is computed here rather than in the browser so version
+    comparison happens once, in the one place that already knows how to
+    read a PEP 440 version. ``docker`` tells the browser that codex
+    cannot install over itself here, so an upgrade means pulling a new
+    image rather than running the update job.
     """
     ts = Timestamp.objects.get(key=Timestamp.Choices.CODEX_VERSION.value)
     if ts.value:
@@ -31,6 +38,8 @@ def version_payload() -> dict[str, str]:
     return {
         "installed": VERSION,
         "latest": latest_version,
+        "outdated": is_outdated(VERSION, ts.value),
+        "docker": is_docker(),
         "warning": DOCKER_IMAGE_DEPRECATED,
     }
 
@@ -41,7 +50,7 @@ class VersionView(AuthGenericAPIView):
     serializer_class = VersionsSerializer
 
     @override
-    def get_object(self) -> dict[str, str]:
+    def get_object(self) -> dict[str, str | bool]:
         """Get the versions."""
         return version_payload()
 
diff --git a/frontend/bun.lock b/frontend/bun.lock
index 46061d43b..712a8b597 100644
--- a/frontend/bun.lock
+++ b/frontend/bun.lock
@@ -26,7 +26,7 @@
         "@unhead/bundler": "^3.3.2",
         "@vitejs/plugin-vue": "^6.0.8",
         "@vue/test-utils": "^2.4.11",
-        "@vue/typescript-plugin": "^3.3.9",
+        "@vue/typescript-plugin": "^3.3.10",
         "happy-dom": "^20.11.2",
         "rollup-plugin-visualizer": "^7.1.1",
         "sass": "^1.102.0",
@@ -332,7 +332,7 @@
 
     "@vue/devtools-shared": ["@vue/devtools-shared@8.1.5", "", {}, "sha512-mhT4zcPFhF+Xk1O4BfhhrbXzpmfqY03fS6xGpcllbQG7lDjhQf8pQHcTIhqQIYx1hfwtHmk/6jM96ele0UxPqQ=="],
 
-    "@vue/language-core": ["@vue/language-core@3.3.9", "", { "dependencies": { "@volar/language-core": "2.4.28", "@vue/compiler-dom": "^3.5.0", "@vue/shared": "^3.5.0", "alien-signals": "^3.2.1", "muggle-string": "^0.4.1", "path-browserify": "^1.0.1", "picomatch": "^4.0.4" } }, "sha512-in/68oAa4BCtVY6n/nkuhLIkV8DHYd2UivedJ6cMZ6UYtlq9jaoaSNUBHYCVO44z3nKg7MdE5OBoHKt5SxeBKQ=="],
+    "@vue/language-core": ["@vue/language-core@3.3.10", "", { "dependencies": { "@volar/language-core": "2.4.28", "@vue/compiler-dom": "^3.5.0", "@vue/shared": "^3.5.0", "alien-signals": "^3.2.1", "muggle-string": "^0.4.1", "path-browserify": "^1.0.1", "picomatch": "^4.0.4" } }, "sha512-CR7ByBbgPHqhxrioKPOcZBqttaozzLNwtkCzXQ+uF8gLPHnUe03srPnGpdtHD3zp+bq5iyVkZ1WNx7W564RPwg=="],
 
     "@vue/reactivity": ["@vue/reactivity@3.5.41", "", { "dependencies": { "@vue/shared": "3.5.41" } }, "sha512-rznsqKM0np0x18EjzF8x88MpEhdNsffbvFbckLL5+oUKz1BxAImEmO7J1ArRYSyo6aQaVoBDp7jEkT91OOxydA=="],
 
@@ -342,11 +342,11 @@
 
     "@vue/server-renderer": ["@vue/server-renderer@3.5.39", "", { "dependencies": { "@vue/compiler-ssr": "3.5.39", "@vue/shared": "3.5.39" }, "peerDependencies": { "vue": "3.5.39" } }, "sha512-yZSakiAGw85rZfG7UM8akMnIF+FmeiNk47uvHf2nVBBSe+dIKUhZuZq9+XgJhbV3nS5Z4ALH23/MpXofW+mbcw=="],
 
-    "@vue/shared": ["@vue/shared@3.5.40", "", {}, "sha512-WxnBtruIqOoV3rA4jeKDWzrYI5h7Cp4+pjwDi8kWGHz+IslhiN+wguLVVhtv2l8VoU02rzDCVfDjgCl1lNpZVg=="],
+    "@vue/shared": ["@vue/shared@3.5.41", "", {}, "sha512-IOnwSCma8j+9xJT6b8H0dEYidC80NsYmNMlZxRsukYcSoGaDBohog5hDxzeUXdFeGWFA++vWvxqOmrr96VlqMA=="],
 
     "@vue/test-utils": ["@vue/test-utils@2.4.11", "", { "dependencies": { "js-beautify": "^1.14.9", "vue-component-type-helpers": "^3.0.0" }, "peerDependencies": { "@vue/compiler-dom": "3.x", "@vue/server-renderer": "3.x", "vue": "3.x" }, "optionalPeers": ["@vue/server-renderer"] }, "sha512-GDqaqZsA6m2E5vNzej0aYiIb6BX8xV9pNSbbbXKOfEYwg7ZNblVX8suyqmUBThq8VIrgAJNxn+z72hVtUeiWHA=="],
 
-    "@vue/typescript-plugin": ["@vue/typescript-plugin@3.3.9", "", { "dependencies": { "@volar/typescript": "2.4.28", "@vue/language-core": "3.3.9", "@vue/shared": "^3.5.0", "path-browserify": "^1.0.1", "vue-component-meta": "3.3.9" } }, "sha512-lU5YLNiuaClZX1U9XwRaGZMeIFFvCin8SrESm5/azzfw/RvYvYj42sspy5/+XfSIZHHPn8Kdc2nm5qZ9C4OFfw=="],
+    "@vue/typescript-plugin": ["@vue/typescript-plugin@3.3.10", "", { "dependencies": { "@volar/typescript": "2.4.28", "@vue/language-core": "3.3.10", "@vue/shared": "^3.5.0", "path-browserify": "^1.0.1", "vue-component-meta": "3.3.10" } }, "sha512-1IzVHNgSrueIsQNETp9I+emLwuhnuw8iV1s9i6wKtfoYPEtg6ZXAgDQKPupedDZ+IQbkm9CSUc3NKODPpJByHg=="],
 
     "@vuetify/loader-shared": ["@vuetify/loader-shared@2.1.2", "", { "dependencies": { "upath": "^2.0.1" }, "peerDependencies": { "vue": "^3.0.0", "vuetify": ">=3" } }, "sha512-X+1jBLmXHkpQEnC0vyOb4rtX2QSkBiFhaFXz8yhQqN2A4vQ6k2nChxN4Ol7VAY5KoqMdFoRMnmNdp/1qYXDQig=="],
 
@@ -810,7 +810,7 @@
 
     "vue": ["vue@3.5.41", "", { "dependencies": { "@vue/compiler-dom": "3.5.41", "@vue/compiler-sfc": "3.5.41", "@vue/runtime-dom": "3.5.41", "@vue/server-renderer": "3.5.41", "@vue/shared": "3.5.41" }, "peerDependencies": { "typescript": "*" }, "optionalPeers": ["typescript"] }, "sha512-2laE0p+aK+/AOPG/XL/WepOs/GlK755LJ1XECi9kDUrz1FKNw8rb2Xzlw9JS1rqEV55nb0ttsKxVlTCcd+R5cg=="],
 
-    "vue-component-meta": ["vue-component-meta@3.3.9", "", { "dependencies": { "@volar/typescript": "2.4.28", "@vue/language-core": "3.3.9", "path-browserify": "^1.0.1" }, "peerDependencies": { "typescript": "*" }, "optionalPeers": ["typescript"] }, "sha512-4u1VmMVjqs9BbKaISBZD7b+dNdqFteh5BYN8xVaXkjjJ66no1sRtDnS6aSs5/P5AzQQGPw10snHTf/z3HpBn2w=="],
+    "vue-component-meta": ["vue-component-meta@3.3.10", "", { "dependencies": { "@volar/typescript": "2.4.28", "@vue/language-core": "3.3.10", "path-browserify": "^1.0.1" }, "peerDependencies": { "typescript": "*" }, "optionalPeers": ["typescript"] }, "sha512-9iZ4hYcaB3k59wmcrUIeX0W5wzdsCHEa1b3pyH6atq3FwCcz+V1a/kRbekZihTZ2Hm/l9dyvjszsMUvnc01tpw=="],
 
     "vue-component-type-helpers": ["vue-component-type-helpers@3.3.7", "", {}, "sha512-Skkhw9agYSgsWqv7bxSOGJZa9SaiJbZVGdXuFWnrzKaQYHnw9qbjD630rw6RyMqDbp54nfLCLw5SZA55if7JLg=="],
 
@@ -892,8 +892,6 @@
 
     "@vue/compiler-sfc/@vue/compiler-ssr": ["@vue/compiler-ssr@3.5.41", "", { "dependencies": { "@vue/compiler-dom": "3.5.41", "@vue/shared": "3.5.41" } }, "sha512-U3v5OejKEGqOI0Wy0+Sz7hGuIFZHA4LSXzrNM3IMIeDyJEBBfTpX26n3SDgToRpP2bLc9FfI2j/kSgcJ8Emq5A=="],
 
-    "@vue/compiler-sfc/@vue/shared": ["@vue/shared@3.5.41", "", {}, "sha512-IOnwSCma8j+9xJT6b8H0dEYidC80NsYmNMlZxRsukYcSoGaDBohog5hDxzeUXdFeGWFA++vWvxqOmrr96VlqMA=="],
-
     "@vue/compiler-sfc/estree-walker": ["estree-walker@2.0.2", "", {}, "sha512-Rfkk/Mp/DL7JVje3u18FxFujQlTNR2q6QfMSMB7AvCBx91NGj/ba3kCfza0f6dVDbw7YlRf/nDrn7pQrCCyQ/w=="],
 
     "@vue/compiler-sfc/magic-string": ["magic-string@0.30.21", "", { "dependencies": { "@jridgewell/sourcemap-codec": "^1.5.5" } }, "sha512-vd2F4YUyEXKGcLHoq+TEyCjxueSeHnFxyyjNp80yg0XV4vUhnDer/lvvlqM/arB5bXQN5K2/3oinyCRyx8T2CQ=="],
@@ -902,13 +900,7 @@
 
     "@vue/devtools-kit/hookable": ["hookable@5.5.3", "", {}, "sha512-Yc+BQe8SvoXH1643Qez1zqLRmbA5rCL+sSmk6TVos0LWVfNIB7PGncdlId77WzLGSIB5KaWgTaNTs2lNVEI6VQ=="],
 
-    "@vue/language-core/@vue/compiler-dom": ["@vue/compiler-dom@3.5.40", "", { "dependencies": { "@vue/compiler-core": "3.5.40", "@vue/shared": "3.5.40" } }, "sha512-pwkx4vqlqOspFstrcmzwkKLePVMD3PT65imRzLhanU2V1Fj4K13g6OXjanOyzw3aTAuRk84BOmY8f3rEHqPaVA=="],
-
-    "@vue/reactivity/@vue/shared": ["@vue/shared@3.5.41", "", {}, "sha512-IOnwSCma8j+9xJT6b8H0dEYidC80NsYmNMlZxRsukYcSoGaDBohog5hDxzeUXdFeGWFA++vWvxqOmrr96VlqMA=="],
-
-    "@vue/runtime-core/@vue/shared": ["@vue/shared@3.5.41", "", {}, "sha512-IOnwSCma8j+9xJT6b8H0dEYidC80NsYmNMlZxRsukYcSoGaDBohog5hDxzeUXdFeGWFA++vWvxqOmrr96VlqMA=="],
-
-    "@vue/runtime-dom/@vue/shared": ["@vue/shared@3.5.41", "", {}, "sha512-IOnwSCma8j+9xJT6b8H0dEYidC80NsYmNMlZxRsukYcSoGaDBohog5hDxzeUXdFeGWFA++vWvxqOmrr96VlqMA=="],
+    "@vue/language-core/@vue/compiler-dom": ["@vue/compiler-dom@3.5.41", "", { "dependencies": { "@vue/compiler-core": "3.5.41", "@vue/shared": "3.5.41" } }, "sha512-oKacVfNglLvGjnS6BXOlGL7EyG2h8X03pqXCjzotRZUaXGjbrTJUnVAQjrCqUnS+lyu31nwQjZY/d817GmCnfw=="],
 
     "@vue/server-renderer/@vue/shared": ["@vue/shared@3.5.39", "", {}, "sha512-l1rrBtBfTnmxvtsvdQDXltUUy8S1Y+ZaqdfUzmAnJkTd8Z8rv5v/ytW+TKiqEOWyHPoqtPlNFSs0lhRmYVSHVA=="],
 
@@ -952,8 +944,6 @@
 
     "vue/@vue/server-renderer": ["@vue/server-renderer@3.5.41", "", { "dependencies": { "@vue/compiler-ssr": "3.5.41", "@vue/runtime-dom": "3.5.41", "@vue/shared": "3.5.41" } }, "sha512-n6hx/pNFfbD6SuyeuMVkvqox8bwf/ET9JlA/kAz/imw8sw++wkqKe2mHX5KutjPpbKE4Z56yTHszoOjGMI9igQ=="],
 
-    "vue/@vue/shared": ["@vue/shared@3.5.41", "", {}, "sha512-IOnwSCma8j+9xJT6b8H0dEYidC80NsYmNMlZxRsukYcSoGaDBohog5hDxzeUXdFeGWFA++vWvxqOmrr96VlqMA=="],
-
     "vue-router/magic-string": ["magic-string@0.30.21", "", { "dependencies": { "@jridgewell/sourcemap-codec": "^1.5.5" } }, "sha512-vd2F4YUyEXKGcLHoq+TEyCjxueSeHnFxyyjNp80yg0XV4vUhnDer/lvvlqM/arB5bXQN5K2/3oinyCRyx8T2CQ=="],
 
     "wrap-ansi/string-width": ["string-width@7.2.0", "", { "dependencies": { "emoji-regex": "^10.3.0", "get-east-asian-width": "^1.0.0", "strip-ansi": "^7.1.0" } }, "sha512-tsaTIkKW9b4N+AEj+SVA+WhJzV7/zMhcSu78mLKWSk7cXMOSHsBKFWUs0fWwq8QyK3MgJBQRX6Gbi4kYbdvGkQ=="],
@@ -978,6 +968,8 @@
 
     "@vue-macros/common/@vue/compiler-sfc/@vue/compiler-ssr": ["@vue/compiler-ssr@3.5.40", "", { "dependencies": { "@vue/compiler-dom": "3.5.40", "@vue/shared": "3.5.40" } }, "sha512-rrE5xiXG663+vHCHa3J9p2z5OcBRjXmoqenprJxAFQxg5pSshzeBiCE6pu46axapRJ2Adk0YDA2BRZVjiHXnhg=="],
 
+    "@vue-macros/common/@vue/compiler-sfc/@vue/shared": ["@vue/shared@3.5.40", "", {}, "sha512-WxnBtruIqOoV3rA4jeKDWzrYI5h7Cp4+pjwDi8kWGHz+IslhiN+wguLVVhtv2l8VoU02rzDCVfDjgCl1lNpZVg=="],
+
     "@vue-macros/common/@vue/compiler-sfc/estree-walker": ["estree-walker@2.0.2", "", {}, "sha512-Rfkk/Mp/DL7JVje3u18FxFujQlTNR2q6QfMSMB7AvCBx91NGj/ba3kCfza0f6dVDbw7YlRf/nDrn7pQrCCyQ/w=="],
 
     "@vue-macros/common/@vue/compiler-sfc/magic-string": ["magic-string@0.30.21", "", { "dependencies": { "@jridgewell/sourcemap-codec": "^1.5.5" } }, "sha512-vd2F4YUyEXKGcLHoq+TEyCjxueSeHnFxyyjNp80yg0XV4vUhnDer/lvvlqM/arB5bXQN5K2/3oinyCRyx8T2CQ=="],
@@ -986,7 +978,7 @@
 
     "@vue/compiler-core/@babel/parser/@babel/types": ["@babel/types@7.29.7", "", { "dependencies": { "@babel/helper-string-parser": "^7.29.7", "@babel/helper-validator-identifier": "^7.29.7" } }, "sha512-4zBIxpPzowiZpusoFkyGVwakdRJUyuH5PxQ/PrqghfdFWWasvnCdPfQXHrenDai+gyLARulZjZowCOj6fjT4pA=="],
 
-    "@vue/language-core/@vue/compiler-dom/@vue/compiler-core": ["@vue/compiler-core@3.5.40", "", { "dependencies": { "@babel/parser": "^7.29.7", "@vue/shared": "3.5.40", "entities": "^7.0.1", "estree-walker": "^2.0.2", "source-map-js": "^1.2.1" } }, "sha512-39E8IgOhTbVDnoJFMKc2DvYnypcZwUqgUhQkccva/0m6FUwtIKSGV7n1hpVmYcFaoRAwf9pBcwnKlCEsN63ZEQ=="],
+    "@vue/language-core/@vue/compiler-dom/@vue/compiler-core": ["@vue/compiler-core@3.5.41", "", { "dependencies": { "@babel/parser": "^7.29.8", "@vue/shared": "3.5.41", "entities": "^7.0.1", "estree-walker": "^2.0.2", "source-map-js": "^1.2.1" } }, "sha512-q0Xtv/F9w2YO/7htQhtiL+Ev2WCJbe5N2hc+XfgyKkEKqWpSxknmT8QOuGdEKNdjPq0c3F7rNpFkTo3Kfrm7pg=="],
 
     "ast-kit/@babel/parser/@babel/types": ["@babel/types@7.29.7", "", { "dependencies": { "@babel/helper-string-parser": "^7.29.7", "@babel/helper-validator-identifier": "^7.29.7" } }, "sha512-4zBIxpPzowiZpusoFkyGVwakdRJUyuH5PxQ/PrqghfdFWWasvnCdPfQXHrenDai+gyLARulZjZowCOj6fjT4pA=="],
 
@@ -1020,8 +1012,6 @@
 
     "@vue/compiler-core/@babel/parser/@babel/types/@babel/helper-string-parser": ["@babel/helper-string-parser@7.29.7", "", {}, "sha512-Pb5ijPrZ89GDH8223L4UP8i6QApWxs04RbPQJTeWDV0/keR2E36MeKnyr6LYmUUvqRRI+Iv87SuF1W6ErINzYw=="],
 
-    "@vue/language-core/@vue/compiler-dom/@vue/compiler-core/@babel/parser": ["@babel/parser@7.29.7", "", { "dependencies": { "@babel/types": "^7.29.7" }, "bin": "./bin/babel-parser.js" }, "sha512-hnORnjP/1P/zFEndoeX+n+t1RwWRJiJpM/jO7FW32Kn9r5+sJB2JWOdYo4L6k78j15eCwY3Gm/7364B1EMwtNg=="],
-
     "@vue/language-core/@vue/compiler-dom/@vue/compiler-core/estree-walker": ["estree-walker@2.0.2", "", {}, "sha512-Rfkk/Mp/DL7JVje3u18FxFujQlTNR2q6QfMSMB7AvCBx91NGj/ba3kCfza0f6dVDbw7YlRf/nDrn7pQrCCyQ/w=="],
 
     "ast-kit/@babel/parser/@babel/types/@babel/helper-string-parser": ["@babel/helper-string-parser@7.29.7", "", {}, "sha512-Pb5ijPrZ89GDH8223L4UP8i6QApWxs04RbPQJTeWDV0/keR2E36MeKnyr6LYmUUvqRRI+Iv87SuF1W6ErINzYw=="],
@@ -1088,16 +1078,12 @@
 
     "@vue-macros/common/@vue/compiler-sfc/@babel/parser/@babel/types/@babel/helper-string-parser": ["@babel/helper-string-parser@7.29.7", "", {}, "sha512-Pb5ijPrZ89GDH8223L4UP8i6QApWxs04RbPQJTeWDV0/keR2E36MeKnyr6LYmUUvqRRI+Iv87SuF1W6ErINzYw=="],
 
-    "@vue/language-core/@vue/compiler-dom/@vue/compiler-core/@babel/parser/@babel/types": ["@babel/types@7.29.7", "", { "dependencies": { "@babel/helper-string-parser": "^7.29.7", "@babel/helper-validator-identifier": "^7.29.7" } }, "sha512-4zBIxpPzowiZpusoFkyGVwakdRJUyuH5PxQ/PrqghfdFWWasvnCdPfQXHrenDai+gyLARulZjZowCOj6fjT4pA=="],
-
     "vitest/vite/rolldown/@rolldown/binding-wasm32-wasi/@emnapi/core": ["@emnapi/core@1.11.1", "", { "dependencies": { "@emnapi/wasi-threads": "1.2.2", "tslib": "^2.4.0" } }, "sha512-RSvbQmHzdKzNsLYa/wHrbc3KN4sYLKAdPZxqiM2HATqv/SBk2/ENSHpvXGaLOMcsAyz0poEGqkmmKYG3OWiJEQ=="],
 
     "vitest/vite/rolldown/@rolldown/binding-wasm32-wasi/@emnapi/runtime": ["@emnapi/runtime@1.11.1", "", { "dependencies": { "tslib": "^2.4.0" } }, "sha512-vgj7R3y3Wgx24IQaGPA/R6YFXLHVMOZ0uVEyIQPaWs+rd1AzfEMXlAC22FYwO1XkKR6NPsq7mUandH8oIRdZFw=="],
 
     "vitest/vite/rolldown/@rolldown/binding-wasm32-wasi/@napi-rs/wasm-runtime": ["@napi-rs/wasm-runtime@1.1.6", "", { "dependencies": { "@tybys/wasm-util": "^0.10.3" }, "peerDependencies": { "@emnapi/core": "^1.7.1", "@emnapi/runtime": "^1.7.1" } }, "sha512-ZLv/JdUfkvOy9eCnnBaGfiO+XimbjebAeO+MRQqD/B+FR1tnRN0tpKSJHRbE8sFfS6aqsXZ67TQjfwfsxULVbg=="],
 
-    "@vue/language-core/@vue/compiler-dom/@vue/compiler-core/@babel/parser/@babel/types/@babel/helper-string-parser": ["@babel/helper-string-parser@7.29.7", "", {}, "sha512-Pb5ijPrZ89GDH8223L4UP8i6QApWxs04RbPQJTeWDV0/keR2E36MeKnyr6LYmUUvqRRI+Iv87SuF1W6ErINzYw=="],
-
     "vitest/vite/rolldown/@rolldown/binding-wasm32-wasi/@emnapi/core/@emnapi/wasi-threads": ["@emnapi/wasi-threads@1.2.2", "", { "dependencies": { "tslib": "^2.4.0" } }, "sha512-c95qOXkHdydNKhscBTebqEC1CVAZpyqOfVfBzQ1qgzyl3gfeldUjIggDbIZgDKsHLgnsM+igH7TJ/eAasaVuMA=="],
   }
 }
diff --git a/frontend/package.json b/frontend/package.json
index 51e95f825..76fbcb86d 100644
--- a/frontend/package.json
+++ b/frontend/package.json
@@ -1,6 +1,6 @@
 {
   "name": "codex",
-  "version": "2.2.7",
+  "version": "2.2.8",
   "private": true,
   "description": "ui for codex api",
   "type": "module",
@@ -37,7 +37,7 @@
     "@unhead/bundler": "^3.3.2",
     "@vitejs/plugin-vue": "^6.0.8",
     "@vue/test-utils": "^2.4.11",
-    "@vue/typescript-plugin": "^3.3.9",
+    "@vue/typescript-plugin": "^3.3.10",
     "happy-dom": "^20.11.2",
     "rollup-plugin-visualizer": "^7.1.1",
     "sass": "^1.102.0",
diff --git a/frontend/src/components/admin/tabs/flag-descriptions.json b/frontend/src/components/admin/tabs/flag-descriptions.json
index 494153240..ebaa593ee 100644
--- a/frontend/src/components/admin/tabs/flag-descriptions.json
+++ b/frontend/src/components/admin/tabs/flag-descriptions.json
@@ -1,7 +1,7 @@
 {
   "AR": "Default age rating applied to comics that carry no age-rating tag. Age-rating restrictions are always in effect. Setting this to Adult is the most secure choice: untagged comics are only visible to users whose Age Rating includes Adult (or who have no Age Rating ceiling set). Setting it to Everyone is the least secure: untagged comics are visible to every user. Intermediate values let progressively more users see untagged comics. Admins are not exempt from age restrictions; set an admin's Age Rating on the Users tab to let them see restricted comics.",
   "AA": "Age-rating ceiling for anonymous sessions (users who are not logged in). Set more restrictively (e.g. Everyone) if your instance is public and you do not wish to show age rated comics by default.",
-  "AU": "If enabled, codex will attempt to update the codex python package once a day and restart the server if an update occurred. Not advisable if running from Docker as running containers aren't meant to hold state and will be rebuilt if you update the image. Look into services that automatically update docker images instead.",
+  "AU": "If enabled, codex will attempt to update the codex python package once a day and restart the server if an update occurred. The Update Codex job on the Jobs tab updates on demand whether or not this is enabled. Not advisable if running from Docker as running containers aren't meant to hold state and will be rebuilt if you update the image. Look into services that automatically update docker images instead.",
   "NU": "By default all Codex features, including bookmarking, are available to users who are not logged in. You may disable this feature and Codex will hide its browser and reader and disable its API and OPDS from anyone who is not logged in as a user.",
   "RG": "By default users' bookmarks and preferences are saved in an anonymous browser session. Users can create a username and password to save their bookmarks between browsers. You may disable this feature. Admins may still create users.",
   "RV": "Require new accounts to verify their email address before activation. New users are created inactive and receive a verification link by email. Has no effect until the SMTP host is configured on the Email tab - new accounts are always active in that case. Existing accounts are unaffected. When on, the registration dialog requires an email address.",
diff --git a/frontend/src/components/admin/tabs/job-tab.vue b/frontend/src/components/admin/tabs/job-tab.vue
index 58d6aa6d9..737472866 100644
--- a/frontend/src/components/admin/tabs/job-tab.vue
+++ b/frontend/src/components/admin/tabs/job-tab.vue
@@ -12,6 +12,7 @@
     </div>
     <AdminSection
       v-for="group in ADMIN_JOBS"
+      :id="groupId(group.title)"
       :key="group.title"
       :title="group.title"
     >
@@ -79,6 +80,25 @@
               <div v-else class="adminCardDesc">
                 {{ job.desc }}
               </div>
+              <!-- Which version this job would install -->
+              <template v-if="isUpdateJob(job)">
+                <div
+                  class="jobVersionNote"
+                  :class="{ jobVersionNoteOutdated: versions.outdated }"
+                >
+                  {{ updateVersionNote }}
+                </div>
+                <div v-if="versions.docker" class="jobVersionNote">
+                  Codex is running in Docker. Containers are rebuilt, not
+                  upgraded in place: pulling a new image is preferable to
+                  updating codex inside this container.
+                  <a :href="GHCR_URL" target="_blank"
+                    >ghcr.io/ajslater/codex<v-icon size="x-small">{{
+                      mdiOpenInNew
+                    }}</v-icon></a
+                  >
+                </div>
+              </template>
             </div>
             <div class="adminCardActions">
               <span v-if="jobLastRun(job)" class="jobLastRun">
@@ -218,7 +238,9 @@
 </template>
 
 <script>
+import { mdiOpenInNew } from "@mdi/js";
 import { mapActions, mapState } from "pinia";
+import { camelCase } from "text-case";
 
 import { ADMIN_JOBS } from "@/choices/admin-jobs.json";
 import AdminSection from "@/components/admin/tabs/admin-section.vue";
@@ -241,6 +263,10 @@ import { useCommonStore } from "@/stores/common";
 
 const SELECT_GROUPS = Object.freeze(["Notify"]);
 const NIGHTLY_JOB_VALUE = "janitor_nightly";
+const UPDATE_JOB_VALUE = "codex_update";
+const GHCR_URL = "https://github.com/ajslater/codex/pkgs/container/codex";
+// The placeholder the server sends while the version cache is cold.
+const LATEST_UNKNOWN = "fetching...";
 Object.freeze(ADMIN_JOBS);
 
 export default {
@@ -257,6 +283,8 @@ export default {
   data() {
     return {
       ADMIN_JOBS,
+      GHCR_URL,
+      mdiOpenInNew,
       // Per-variant-job selected variant value, keyed by job.value.
       variantSelections: {},
       // Per-group select value for SELECT_GROUPS (Notify).
@@ -267,6 +295,7 @@ export default {
     };
   },
   computed: {
+    ...mapState(useCommonStore, ["versions"]),
     ...mapState(useCommonStore, {
       formSuccess: (state) => state.form.success,
       formErrors: (state) => state.form.errors,
@@ -274,6 +303,18 @@ export default {
     ...mapState(useAdminStore, {
       allStatuses: (state) => state.allLibrarianStatuses,
     }),
+    updateVersionNote() {
+      const { installed, latest, outdated, docker } = this.versions;
+      if (!latest || latest === LATEST_UNKNOWN) {
+        return "The latest version is unknown. Check for it above.";
+      }
+      if (!outdated) {
+        return `Codex v${installed} is the latest version`;
+      }
+      return docker
+        ? `Codex v${latest} is available`
+        : `Will install codex v${latest}`;
+    },
     groupSelectMaps() {
       const maps = {};
       for (const group of ADMIN_JOBS) {
@@ -309,6 +350,10 @@ export default {
     },
   },
   watch: {
+    // Re-scroll if the deep link fires while already on the Jobs tab.
+    "$route.hash"() {
+      this.maybeScroll();
+    },
     allStatuses() {
       // Auto-collapse panels for jobs that are no longer active.
       for (const group of ADMIN_JOBS) {
@@ -323,9 +368,48 @@ export default {
   },
   created() {
     this.loadAllStatuses();
+    // Powers the "which version would this install" note below.
+    this.loadVersions();
+  },
+  mounted() {
+    this.maybeScroll();
   },
   methods: {
     ...mapActions(useAdminStore, ["librarianTask", "loadAllStatuses"]),
+    ...mapActions(useCommonStore, ["loadVersions"]),
+
+    // --- Codex version ---
+
+    isUpdateJob(job) {
+      return job.value === UPDATE_JOB_VALUE;
+    },
+
+    // --- Deep links ---
+
+    groupId(title) {
+      // "Codex Software" -> "codexSoftware". Anchor for deep links like
+      // the settings drawer's "upgrade to codex" link.
+      return camelCase(title);
+    },
+    maybeScroll() {
+      const hash = this.$route.hash;
+      if (!hash) return;
+      this.$nextTick(() => {
+        /*
+         * Scoped to this instance, not document.getElementById: the
+         * admin tabs render a router-view per tab inside a v-window,
+         * so a second, hidden copy of this tab can be in the DOM with
+         * the same section ids.
+         */
+        const el = this.$el.querySelector(hash);
+        /*
+         * Instant, not smooth: a smooth scroll is animated frame by
+         * frame and any competing scroll during the tab transition
+         * abandons it partway. A deep link should just arrive.
+         */
+        if (el) el.scrollIntoView({ block: "start" });
+      });
+    },
 
     // --- Variant helpers ---
 
@@ -518,6 +602,16 @@ export default {
   margin-left: 8px;
 }
 
+.jobVersionNote {
+  font-size: 0.9em;
+  padding-top: 2px;
+  color: rgb(var(--v-theme-textDisabled));
+}
+
+.jobVersionNoteOutdated {
+  color: rgb(var(--v-theme-primary));
+}
+
 .variantRow {
   padding-top: 4px;
 }
diff --git a/frontend/src/components/settings/version-footer.vue b/frontend/src/components/settings/version-footer.vue
index 791ec109e..17c38ed42 100644
--- a/frontend/src/components/settings/version-footer.vue
+++ b/frontend/src/components/settings/version-footer.vue
@@ -1,13 +1,35 @@
 <template>
-  <v-footer id="version-footer" :title="versionTitle">
-    <a id="version" href="https://github.com/ajslater/codex/" target="_blank">
+  <v-footer id="version-footer">
+    <a
+      id="version"
+      href="https://github.com/ajslater/codex/"
+      target="_blank"
+      title="Codex source code"
+    >
       <v-icon id="repoIcon" size="x-small">{{ mdiSourceRepository }}</v-icon>
       codex v{{ versions.installed
       }}<v-icon size="x-small">{{ mdiOpenInNew }}</v-icon></a
     >
-    <div v-if="outdated" id="latest">
-      codex v{{ versions.latest }} is available
-    </div>
+    <!--
+      In a container codex can't install over itself. Send admins to the
+      image registry instead of to a job that would only fail.
+    -->
+    <a
+      v-if="outdated && versions.docker"
+      id="latest"
+      :href="GHCR_URL"
+      target="_blank"
+      title="Docker image repo"
+      >{{ upgradeText }}<v-icon size="x-small">{{ mdiOpenInNew }}</v-icon></a
+    >
+    <router-link
+      v-else-if="outdated"
+      id="latest"
+      :to="UPDATE_ROUTE"
+      title="Upgrade Codex"
+    >
+      {{ upgradeText }}
+    </router-link>
     <div v-if="versions.warning" id="warning">
       {{ versions.warning }}
     </div>
@@ -20,27 +42,37 @@ import { mapActions, mapState } from "pinia";
 
 import { useAuthStore } from "@/stores/auth";
 import { useCommonStore } from "@/stores/common";
+
+// The Codex Software job group, where the Update Codex job lives.
+const UPDATE_ROUTE = Object.freeze({
+  name: "admin-jobs",
+  hash: "#codexSoftware",
+});
+const GHCR_URL = "https://github.com/ajslater/codex/pkgs/container/codex";
+
 export default {
   name: "VersionFooter",
   data() {
     return {
       mdiOpenInNew,
       mdiSourceRepository,
+      GHCR_URL,
+      UPDATE_ROUTE,
     };
   },
   computed: {
     ...mapState(useCommonStore, ["versions"]),
     ...mapState(useAuthStore, ["isUserAdmin"]),
     outdated: function () {
-      return (
-        this.isUserAdmin &&
-        this.semverGreaterThan(this.versions.latest > this.versions.installed)
-      );
+      /*
+       * The server compares versions. It's the only side that can read
+       * a PEP 440 version correctly, and only admins can act on the
+       * answer anyway.
+       */
+      return Boolean(this.isUserAdmin && this.versions.outdated);
     },
-    versionTitle: function () {
-      return this.outdated
-        ? `v${this.versions.latest} is available`
-        : "up to date";
+    upgradeText: function () {
+      return `upgrade to codex v${this.versions.latest}`;
     },
   },
   created() {
@@ -48,24 +80,6 @@ export default {
   },
   methods: {
     ...mapActions(useCommonStore, ["loadVersions"]),
-    semverGreaterThan(a, b) {
-      try {
-        if (!a || !b) {
-          return false;
-        }
-        const aParts = a.split(".");
-        const bParts = b.split(".");
-
-        for (const [i, aPart] of aParts.entries()) {
-          if (+aPart > +Reflect.get(bParts, i)) {
-            return true;
-          }
-        }
-      } catch (error) {
-        console.debug("compare codex versions", a, ">", b, error);
-      }
-      return false;
-    },
   },
 };
 </script>
@@ -91,7 +105,12 @@ export default {
 }
 
 #latest {
-  color: rgb(var(--v-theme-textSecondary));
+  display: block;
+  color: rgb(var(--v-theme-primary));
+}
+
+#latest:hover {
+  color: rgb(var(--v-theme-linkHover)) !important;
 }
 
 #warning {
diff --git a/frontend/src/stores/common.js b/frontend/src/stores/common.js
index 4982e0d26..eb8d5fba8 100644
--- a/frontend/src/stores/common.js
+++ b/frontend/src/stores/common.js
@@ -43,6 +43,8 @@ export const useCommonStore = defineStore("common", {
 
       installed: CODEX_PACKAGE_VERSION,
       latest: undefined,
+      // The server decides this, in /api/v4/version.
+      outdated: false,
     },
     timestamp: Date.now(),
     isSettingsDrawerOpen: false,
diff --git a/frontend/tests/unit/job-tab-update-note.test.js b/frontend/tests/unit/job-tab-update-note.test.js
new file mode 100644
index 000000000..e392904b7
--- /dev/null
+++ b/frontend/tests/unit/job-tab-update-note.test.js
@@ -0,0 +1,77 @@
+/*
+ * The Update Codex job says which version it would install.
+ *
+ * In Docker it can't install anything — the runtime image has no pip —
+ * so it points at the image registry instead of promising an upgrade.
+ */
+import { createTestingPinia } from "@pinia/testing";
+import { mount } from "@vue/test-utils";
+import { describe, expect, test } from "vitest";
+
+import AdminJobsTab from "@/components/admin/tabs/job-tab.vue";
+import vuetify from "@/plugins/vuetify";
+
+const GHCR_URL = "https://github.com/ajslater/codex/pkgs/container/codex";
+
+function mountTab({
+  installed = "1.0.0",
+  latest = "2.0.0",
+  outdated = true,
+  docker = false,
+} = {}) {
+  const pinia = createTestingPinia({
+    initialState: {
+      auth: { user: { isStaff: true } },
+      admin: { allLibrarianStatuses: {} },
+      common: { versions: { installed, latest, outdated, docker } },
+    },
+  });
+  return mount(AdminJobsTab, {
+    global: {
+      plugins: [vuetify, pinia],
+      mocks: { $route: { hash: "" } },
+    },
+  });
+}
+
+function notes(wrapper) {
+  return wrapper.findAll(".jobVersionNote").map((n) => n.text());
+}
+
+describe("AdminJobsTab — Update Codex version note", () => {
+  test("names the version it would install", () => {
+    const wrapper = mountTab();
+
+    expect(notes(wrapper)).toStrictEqual(["Will install codex v2.0.0"]);
+  });
+
+  test("says so when there is nothing to install", () => {
+    const wrapper = mountTab({ latest: "1.0.0", outdated: false });
+
+    expect(notes(wrapper)[0]).toBe("Codex v1.0.0 is the latest version");
+  });
+
+  test("admits when the latest version has not been fetched yet", () => {
+    const wrapper = mountTab({ latest: "fetching...", outdated: false });
+
+    expect(notes(wrapper)[0]).toContain("latest version is unknown");
+  });
+
+  test("in docker it recommends a new image and links to the registry", () => {
+    const wrapper = mountTab({ docker: true });
+
+    const text = notes(wrapper).join(" ");
+    expect(text).toContain("Codex v2.0.0 is available");
+    expect(text).toContain("pulling a new image");
+    const link = wrapper
+      .findAll("a")
+      .find((a) => a.attributes("href") === GHCR_URL);
+    expect(link).toBeTruthy();
+  });
+
+  test("the codex software section is anchored for deep links", () => {
+    const wrapper = mountTab();
+
+    expect(wrapper.find("#codexSoftware").exists()).toBe(true);
+  });
+});
diff --git a/frontend/tests/unit/version-footer.test.js b/frontend/tests/unit/version-footer.test.js
new file mode 100644
index 000000000..c2c8a726e
--- /dev/null
+++ b/frontend/tests/unit/version-footer.test.js
@@ -0,0 +1,93 @@
+/*
+ * The settings drawer's upgrade call to action.
+ *
+ * It links to the admin jobs tab, where the Update Codex job lives, so
+ * only admins see it — except in Docker, where codex can't install over
+ * itself and the upgrade is a new image from the registry. Whether a
+ * newer version exists is decided by the server and arrives as
+ * ``versions.outdated``; the component used to compare versions itself
+ * and got it wrong in two different ways.
+ */
+import { createTestingPinia } from "@pinia/testing";
+import { mount } from "@vue/test-utils";
+import { describe, expect, test } from "vitest";
+
+import VersionFooter from "@/components/settings/version-footer.vue";
+import vuetify from "@/plugins/vuetify";
+
+const GHCR_URL = "https://github.com/ajslater/codex/pkgs/container/codex";
+
+// Captures ``to`` so the deep link target can be asserted.
+const RouterLinkStub = {
+  name: "RouterLink",
+  props: ["to"],
+  template: "<a :id='$attrs.id' :title='$attrs.title'><slot /></a>",
+};
+
+function mountFooter({ isStaff = true, outdated = true, docker = false } = {}) {
+  const pinia = createTestingPinia({
+    initialState: {
+      auth: { user: { isStaff } },
+      common: {
+        versions: {
+          installed: "1.0.0",
+          latest: "2.0.0",
+          outdated,
+          docker,
+          warning: "",
+        },
+      },
+    },
+  });
+  return mount(VersionFooter, {
+    global: {
+      plugins: [vuetify, pinia],
+      stubs: { RouterLink: RouterLinkStub },
+    },
+  });
+}
+
+describe("VersionFooter", () => {
+  test("admins get a link to the update job", () => {
+    const wrapper = mountFooter();
+
+    const link = wrapper.findComponent(RouterLinkStub);
+    expect(link.exists()).toBe(true);
+    expect(link.props("to")).toStrictEqual({
+      name: "admin-jobs",
+      hash: "#codexSoftware",
+    });
+    expect(link.text()).toContain("upgrade to codex v2.0.0");
+    expect(link.attributes("title")).toBe("Upgrade Codex");
+  });
+
+  test("in docker the link goes to the image registry instead", () => {
+    const wrapper = mountFooter({ docker: true });
+
+    expect(wrapper.findComponent(RouterLinkStub).exists()).toBe(false);
+    const link = wrapper.find("#latest");
+    expect(link.attributes("href")).toBe(GHCR_URL);
+    expect(link.attributes("title")).toBe("Docker image repo");
+    expect(link.text()).toContain("upgrade to codex v2.0.0");
+  });
+
+  test("no announcement for non-admins", () => {
+    const wrapper = mountFooter({ isStaff: false });
+
+    expect(wrapper.find("#latest").exists()).toBe(false);
+  });
+
+  test("no announcement when up to date", () => {
+    const wrapper = mountFooter({ outdated: false });
+
+    expect(wrapper.find("#latest").exists()).toBe(false);
+  });
+
+  test("the installed version links to the source", () => {
+    const wrapper = mountFooter({ outdated: false });
+
+    const version = wrapper.find("#version");
+    expect(version.text()).toContain("codex v1.0.0");
+    expect(version.attributes("title")).toBe("Codex source code");
+  });
+});
diff --git a/pyproject.toml b/pyproject.toml
index 4c0846971..e49035bd5 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -15,7 +15,7 @@ dependencies = [
   "adrf~=0.1.12",
   "bidict~=0.23",
   "channels~=4.2",
-  "comicbox[pdf]~=4.8.1",
+  "comicbox[pdf]~=4.8.2",
   "cryptography>=48.0.0",
   "dateparser~=1.2",
   "django-allauth[socialaccount]~=65.13",
@@ -49,7 +49,7 @@ readme = "README.md"
 requires-python = ">=3.12"
 license = "GPL-3.0-only"
 name = "codex"
-version = "2.2.7"
+version = "2.2.8"
 [[project.authors]]
 name = "AJ Slater"
 email = "aj@slater.net"
diff --git a/test-proxy/server.conf b/test-proxy/server.conf
index 266e65d6c..34223383d 100644
--- a/test-proxy/server.conf
+++ b/test-proxy/server.conf
@@ -33,6 +33,9 @@ server {
     # proxy_set_header  X-Forwarded-Ssl   on;
     proxy_set_header X-Real-IP $remote_addr;
     proxy_set_header X-Scheme $scheme;
+    # nginx hides the upstream Server header by default and substitutes its
+    # own; un-hide it so clients still see "Server: codex/<version>".
+    proxy_pass_header Server;
     # proxy_set_header Remote-User 'admin';
     # WS — $connection_upgrade is mapped from $http_upgrade in nginx.conf so
     # only real WebSocket requests carry "Connection: upgrade".
diff --git a/tests/test_janitor_codex_update.py b/tests/test_janitor_codex_update.py
new file mode 100644
index 000000000..da555dd73
--- /dev/null
+++ b/tests/test_janitor_codex_update.py
@@ -0,0 +1,210 @@
+"""
+Codex self-update: gating, installer selection, failure and restart.
+
+The updater used to check the Auto Update admin flag here, which meant
+the admin's own Update Codex button did nothing while the flag was off
+(and it defaults to off). The flag now gates only the nightly path, in
+:mod:`codex.librarian.bookmark.latest_version`.
+"""
+
+from __future__ import annotations
+
+import subprocess
+import sys
+from contextlib import contextmanager
+from multiprocessing import Event
+from threading import Lock
+from typing import TYPE_CHECKING, override
+from unittest.mock import patch
+
+from django.test import TestCase
+from loguru import logger
+
+from codex.librarian.restarter.tasks import CodexRestartTask
+from codex.librarian.scribe.janitor.janitor import Janitor
+from codex.models.admin import Timestamp
+from codex.startup import init_timestamps
+
+if TYPE_CHECKING:
+    from collections.abc import Generator
+
+_MODULE = "codex.librarian.scribe.janitor.update"
+_INSTALLED = "1.0.0"
+# find_spec's return value is only ever truthiness-tested. A uv or
+# pipx managed environment really has no pip, so pin the choice
+# rather than letting the test read whatever this venv happens to be.
+_PIP_FOUND = object()
+
+
+@contextmanager
+def _capture_logs() -> Generator[list[str]]:
+    """Collect loguru INFO+ messages emitted inside the ``with`` block."""
+    records: list[str] = []
+    sink_id = logger.add(records.append, level="INFO", format="{message}")
+    try:
+        yield records
+    finally:
+        logger.remove(sink_id)
+
+
+class _FakeQueue:
+    """Record tasks put on the librarian queue without touching multiprocessing."""
+
+    def __init__(self) -> None:
+        self.items: list = []
+
+    def put(self, item) -> None:
+        self.items.append(item)
+
+
+class CodexUpdateTests(TestCase):
+    """Janitor.update_codex."""
+
+    @override
+    def setUp(self) -> None:
+        init_timestamps()
+        self.queue = _FakeQueue()  # pyright: ignore[reportUninitializedInstanceVariable]
+        self.janitor = Janitor(  # pyright: ignore[reportUninitializedInstanceVariable]
+            logger, self.queue, Lock(), Event(), online_tag_thread=None
+        )
+
+    @staticmethod
+    def _set_latest(value: str) -> None:
+        Timestamp.objects.filter(key=Timestamp.Choices.CODEX_VERSION.value).update(
+            value=value
+        )
+
+    @property
+    def _restarts(self) -> list:
+        return [t for t in self.queue.items if isinstance(t, CodexRestartTask)]
+
+    def test_up_to_date_does_not_install(self) -> None:
+        self._set_latest(_INSTALLED)
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.subprocess.run") as run,
+        ):
+            self.janitor.update_codex(force=False)
+        run.assert_not_called()
+        assert not self._restarts
+
+    def test_outdated_installs_with_pip(self) -> None:
+        """The common case: pip is importable, so upgrade with this python."""
+        self._set_latest("2.0.0")
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.find_spec", return_value=_PIP_FOUND),
+            patch(f"{_MODULE}.get_version", return_value=_INSTALLED),
+            patch(f"{_MODULE}.subprocess.run") as run,
+        ):
+            self.janitor.update_codex(force=False)
+        args, kwargs = run.call_args
+        assert args[0] == (sys.executable, "-m", "pip", "install", "--upgrade", "codex")
+        assert kwargs["check"] is True
+        assert kwargs["capture_output"] is True
+        # A hung installer must not wedge the scribe thread forever.
+        assert kwargs["timeout"] > 0
+
+    def test_force_installs_when_up_to_date(self) -> None:
+        """Forcing ignores the version check and the admin flag alike."""
+        self._set_latest(_INSTALLED)
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.find_spec", return_value=_PIP_FOUND),
+            patch(f"{_MODULE}.get_version", return_value=_INSTALLED),
+            patch(f"{_MODULE}.subprocess.run") as run,
+        ):
+            self.janitor.update_codex(force=True)
+        run.assert_called_once()
+
+    def test_uv_fallback_when_pip_is_missing(self) -> None:
+        """Uv and pipx environments have no pip."""
+        self._set_latest("2.0.0")
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.get_version", return_value=_INSTALLED),
+            patch(f"{_MODULE}.find_spec", return_value=None),
+            patch(f"{_MODULE}.which", return_value="/opt/bin/uv"),
+            patch(f"{_MODULE}.subprocess.run") as run,
+        ):
+            self.janitor.update_codex(force=False)
+        assert run.call_args[0][0] == (
+            "/opt/bin/uv",
+            "pip",
+            "install",
+            "--upgrade",
+            "--python",
+            sys.executable,
+            "codex",
+        )
+
+    def test_no_installer_logs_an_error(self) -> None:
+        """The docker image strips pip. Say so instead of failing silently."""
+        self._set_latest("2.0.0")
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.find_spec", return_value=None),
+            patch(f"{_MODULE}.which", return_value=None),
+            patch(f"{_MODULE}.is_docker", return_value=True),
+            patch(f"{_MODULE}.subprocess.run") as run,
+            _capture_logs() as logs,
+        ):
+            self.janitor.update_codex(force=False)
+        run.assert_not_called()
+        assert any("neither pip nor uv" in line for line in logs)
+        assert any("Docker" in line for line in logs)
+        assert not self._restarts
+
+    def test_failed_install_does_not_restart(self) -> None:
+        """A pip that exits nonzero must not look like a successful update."""
+        self._set_latest("2.0.0")
+        error = subprocess.CalledProcessError(
+            1, "pip", stderr="No matching distribution"
+        )
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.find_spec", return_value=_PIP_FOUND),
+            patch(f"{_MODULE}.get_version", return_value="2.0.0"),
+            patch(f"{_MODULE}.subprocess.run", side_effect=error),
+            _capture_logs() as logs,
+        ):
+            self.janitor.update_codex(force=False)
+        assert not self._restarts
+        assert any("No matching distribution" in line for line in logs)
+
+    def test_timed_out_install_does_not_restart(self) -> None:
+        self._set_latest("2.0.0")
+        error = subprocess.TimeoutExpired("pip", 600)
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.find_spec", return_value=_PIP_FOUND),
+            patch(f"{_MODULE}.get_version", return_value="2.0.0"),
+            patch(f"{_MODULE}.subprocess.run", side_effect=error),
+            _capture_logs() as logs,
+        ):
+            self.janitor.update_codex(force=False)
+        assert not self._restarts
+        assert any("timed out" in line for line in logs)
+
+    def test_new_version_restarts(self) -> None:
+        self._set_latest("2.0.0")
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.find_spec", return_value=_PIP_FOUND),
+            patch(f"{_MODULE}.get_version", return_value="2.0.0"),
+            patch(f"{_MODULE}.subprocess.run"),
+        ):
+            self.janitor.update_codex(force=False)
+        assert len(self._restarts) == 1
+
+    def test_same_version_does_not_restart(self) -> None:
+        """Reinstalling the same version is not a reason to bounce the server."""
+        self._set_latest("2.0.0")
+        with (
+            patch(f"{_MODULE}.VERSION", _INSTALLED),
+            patch(f"{_MODULE}.find_spec", return_value=_PIP_FOUND),
+            patch(f"{_MODULE}.get_version", return_value=_INSTALLED),
+            patch(f"{_MODULE}.subprocess.run"),
+        ):
+            self.janitor.update_codex(force=False)
+        assert not self._restarts
diff --git a/tests/test_latest_version_fetch.py b/tests/test_latest_version_fetch.py
new file mode 100644
index 000000000..56e03f296
--- /dev/null
+++ b/tests/test_latest_version_fetch.py
@@ -0,0 +1,163 @@
+"""
+The PyPI latest-version fetch: caching, backoff and the update chain.
+
+Nothing ever asked for the update half of this before: the nightly
+janitor queued a bare version check and no caller passed ``update``, so
+the Auto Update admin flag promised a daily update that could not
+happen. The nightly task now forces the fetch and asks it to chain.
+"""
+
+from __future__ import annotations
+
+from threading import Lock
+from typing import override
+from unittest.mock import patch
+
+import pytest
+from django.test import TestCase
+from loguru import logger
+
+from codex.choices.admin import AdminFlagChoices
+from codex.librarian.bookmark.latest_version import (
+    CodexLatestVersionUpdater,
+    _FetchGate,
+)
+from codex.librarian.bookmark.tasks import CodexLatestVersionTask
+from codex.librarian.scribe.janitor.janitor import _NIGHTLY_TASKS
+from codex.librarian.scribe.janitor.tasks import JanitorCodexUpdateTask
+from codex.models.admin import AdminFlag, Timestamp
+from codex.startup import init_admin_flags, init_timestamps
+
+_MODULE = "codex.librarian.bookmark.latest_version"
+_LATEST = "9999.0.0"
+
+
+class _FakeQueue:
+    """Record tasks put on the librarian queue without touching multiprocessing."""
+
+    def __init__(self) -> None:
+        self.items: list = []
+
+    def put(self, item) -> None:
+        self.items.append(item)
+
+
+def test_nightly_version_check_forces_a_fetch_and_may_update() -> None:
+    """The only path that can trigger an automatic update."""
+    assert CodexLatestVersionTask(force=True, update=True) in _NIGHTLY_TASKS
+
+
+class LatestVersionFetchTests(TestCase):
+    """CodexLatestVersionUpdater.update_latest_version."""
+
+    @override
+    def setUp(self) -> None:
+        init_timestamps()
+        init_admin_flags()
+        _FetchGate.next_attempt = 0.0
+        self.queue = _FakeQueue()  # pyright: ignore[reportUninitializedInstanceVariable]
+        self.updater = CodexLatestVersionUpdater(logger, self.queue, Lock())  # pyright: ignore[reportUninitializedInstanceVariable, reportArgumentType]  # ty: ignore[invalid-argument-type]
+
+    @override
+    def tearDown(self) -> None:
+        _FetchGate.next_attempt = 0.0
+
+    @staticmethod
+    def _set_auto_update(*, on: bool) -> None:
+        AdminFlag.objects.filter(key=AdminFlagChoices.AUTO_UPDATE.value).update(on=on)
+
+    @staticmethod
+    def _set_latest(value: str) -> None:
+        Timestamp.objects.filter(key=Timestamp.Choices.CODEX_VERSION.value).update(
+            value=value
+        )
+
+    @staticmethod
+    def _cached_latest() -> str:
+        return Timestamp.objects.get(key=Timestamp.Choices.CODEX_VERSION.value).value
+
+    @property
+    def _update_tasks(self) -> list:
+        return [t for t in self.queue.items if isinstance(t, JanitorCodexUpdateTask)]
+
+    def test_forced_fetch_caches_the_latest_version(self) -> None:
+        with patch.object(
+            CodexLatestVersionUpdater, "_fetch_latest_version", return_value=_LATEST
+        ):
+            self.updater.update_latest_version(force=True)
+        assert self._cached_latest() == _LATEST
+
+    def test_fetch_queues_an_update_when_auto_update_is_on(self) -> None:
+        self._set_auto_update(on=True)
+        with patch.object(
+            CodexLatestVersionUpdater, "_fetch_latest_version", return_value=_LATEST
+        ):
+            self.updater.update_latest_version(force=True, update=True)
+        assert len(self._update_tasks) == 1
+
+    def test_no_update_when_auto_update_is_off(self) -> None:
+        """Off by default, and off means off."""
+        self._set_auto_update(on=False)
+        with patch.object(
+            CodexLatestVersionUpdater, "_fetch_latest_version", return_value=_LATEST
+        ):
+            self.updater.update_latest_version(force=True, update=True)
+        assert not self._update_tasks
+
+    def test_no_update_when_the_fetch_fails(self) -> None:
+        """Never update against a version this run could not confirm."""
+        self._set_auto_update(on=True)
+        self._set_latest("")
+        with (
+            patch.object(
+                CodexLatestVersionUpdater,
+                "_fetch_latest_version",
+                side_effect=TimeoutError,
+            ),
+            pytest.raises(TimeoutError),
+        ):
+            self.updater.update_latest_version(force=True, update=True)
+        assert not self._update_tasks
+        # A failed fetch starts a cooldown so an outage isn't retried
+        # once per request while the cache is empty.
+        assert _FetchGate.next_attempt > 0.0
+
+    def test_backoff_skips_an_unforced_fetch(self) -> None:
+        self._set_latest("")
+        _FetchGate.next_attempt = float("inf")
+        with patch.object(CodexLatestVersionUpdater, "_fetch_latest_version") as fetch:
+            self.updater.update_latest_version(force=False)
+        fetch.assert_not_called()
+
+    def test_in_flight_fetch_is_not_duplicated(self) -> None:
+        """Every /api/v4/version hit queues one of these while the cache is empty."""
+        self._set_latest("")
+        assert _FetchGate.lock.acquire(blocking=False)
+        try:
+            with patch.object(
+                CodexLatestVersionUpdater, "_fetch_latest_version"
+            ) as fetch:
+                self.updater.update_latest_version(force=True)
+            fetch.assert_not_called()
+        finally:
+            _FetchGate.lock.release()
+
+    def test_fresh_cache_is_not_refetched(self) -> None:
+        self._set_latest(_LATEST)
+        with patch.object(CodexLatestVersionUpdater, "_fetch_latest_version") as fetch:
+            self.updater.update_latest_version(force=False)
+        fetch.assert_not_called()
+
+    def test_locked_database_skips_everything(self) -> None:
+        db_write_lock = Lock()
+        db_write_lock.acquire()
+        try:
+            updater = CodexLatestVersionUpdater(logger, self.queue, db_write_lock)  # pyright: ignore[reportArgumentType]  # ty: ignore[invalid-argument-type]
+            with patch.object(
+                CodexLatestVersionUpdater, "_fetch_latest_version"
+            ) as fetch:
+                updater.update_latest_version(force=True, update=True)
+            fetch.assert_not_called()
+        finally:
+            db_write_lock.release()
+        assert not self._update_tasks
diff --git a/tests/test_scribe_priority.py b/tests/test_scribe_priority.py
index 3549db194..b267b439b 100644
--- a/tests/test_scribe_priority.py
+++ b/tests/test_scribe_priority.py
@@ -9,9 +9,10 @@
 
 from __future__ import annotations
 
-from codex.librarian.scribe.janitor.janitor import _JANITOR_METHOD_MAP
+from codex.librarian.scribe.janitor.janitor import _JANITOR_METHOD_MAP, _NIGHTLY_TASKS
 from codex.librarian.scribe.janitor.tasks import JanitorFolderRelationsCheckTask
 from codex.librarian.scribe.priority import _SCRIBE_TASK_PRIORITY, get_task_priority
+from codex.librarian.scribe.tasks import ScribeTask
 
 
 def test_scribe_janitor_tasks_are_priority_rankable() -> None:
@@ -25,6 +26,19 @@ def test_scribe_janitor_tasks_are_priority_rankable() -> None:
     )
 
 
+def test_nightly_scribe_tasks_are_priority_rankable() -> None:
+    """The nightly fan-out queues scribe tasks, which must all be rankable."""
+    missing = sorted(
+        type(task).__name__
+        for task in _NIGHTLY_TASKS
+        if isinstance(task, ScribeTask) and type(task) not in _SCRIBE_TASK_PRIORITY
+    )
+    assert not missing, (
+        "Nightly scribe tasks absent from _SCRIBE_TASK_PRIORITY "
+        f"(get_task_priority would raise): {missing}"
+    )
+
+
 def test_get_task_priority_folder_relations_check() -> None:
     """The reported crash: ranking JanitorFolderRelationsCheckTask must not raise."""
     priority, now = get_task_priority(JanitorFolderRelationsCheckTask())
diff --git a/tests/test_version_outdated.py b/tests/test_version_outdated.py
new file mode 100644
index 000000000..12f9a57d4
--- /dev/null
+++ b/tests/test_version_outdated.py
@@ -0,0 +1,103 @@
+"""
+Version comparison and the version payload the browser reads.
+
+``outdated`` used to be computed in javascript, wrongly: the comparison
+returned true on the first greater version part without ever stopping on
+a lesser one, and it was called with one argument instead of two so it
+returned false always. It lives here now, on the side that can read a
+PEP 440 version.
+"""
+
+from __future__ import annotations
+
+from queue import SimpleQueue
+from typing import override
+from unittest.mock import patch
+
+import pytest
+from django.test import TestCase
+
+from codex.librarian.bookmark.tasks import CodexLatestVersionTask
+from codex.models.admin import Timestamp
+from codex.startup import init_timestamps
+from codex.version import is_outdated
+from codex.views.version import version_payload
+
+
+@pytest.mark.parametrize(
+    ("installed", "latest", "expected"),
+    [
+        ("1.0.0", "1.0.1", True),
+        ("1.0.0", "2.0.0", True),
+        ("1.0.0", "1.0.0", False),
+        ("1.0.1", "1.0.0", False),
+        # The old javascript read this pair as outdated: 9 > 0 in the
+        # third part returned true before the second part could veto.
+        ("1.1.0", "1.0.9", False),
+        ("1.0.9", "1.1.0", True),
+        # A source checkout has no distribution metadata to report.
+        ("test", "2.0.0", False),
+        ("2.0.0", "not a version", False),
+        # Cold cache. Both of these used to raise InvalidVersion.
+        ("1.0.0", "", False),
+        ("1.0.0", "fetching...", False),
+        ("", "1.0.0", False),
+        # Never move a stable install onto a prerelease.
+        ("1.0.0", "1.1.0a1", False),
+        ("1.1.0a1", "1.1.0a2", True),
+        ("1.1.0a1", "1.1.0", True),
+    ],
+)
+def test_is_outdated(installed: str, latest: str, *, expected: bool) -> None:
+    """The version comparison is total: unparseable means "not outdated"."""
+    assert is_outdated(installed, latest) is expected
+
+
+class VersionPayloadTests(TestCase):
+    """The /api/v4/version payload."""
+
+    @override
+    def setUp(self) -> None:
+        init_timestamps()
+
+    @staticmethod
+    def _set_latest(value: str) -> None:
+        Timestamp.objects.filter(key=Timestamp.Choices.CODEX_VERSION.value).update(
+            value=value
+        )
+
+    def test_outdated_when_latest_is_newer(self) -> None:
+        self._set_latest("9999.0.0")
+        with patch("codex.views.version.VERSION", "1.0.0"):
+            payload = version_payload()
+        assert payload["latest"] == "9999.0.0"
+        assert payload["outdated"] is True
+
+    def test_not_outdated_when_current(self) -> None:
+        self._set_latest("1.0.0")
+        with patch("codex.views.version.VERSION", "1.0.0"):
+            payload = version_payload()
+        assert payload["outdated"] is False
+
+    def test_reports_docker(self) -> None:
+        """In a container the browser links to the image registry instead."""
+        self._set_latest("9999.0.0")
+        with (
+            patch("codex.views.version.VERSION", "1.0.0"),
+            patch("codex.views.version.is_docker", return_value=True),
+        ):
+            payload = version_payload()
+        assert payload["docker"] is True
+
+    def test_cold_cache_is_not_outdated_and_queues_a_fetch(self) -> None:
+        """An unfilled cache reports the placeholder, never an update."""
+        self._set_latest("")
+        queue = SimpleQueue()
+        with (
+            patch("codex.views.version.VERSION", "1.0.0"),
+            patch("codex.views.version.LIBRARIAN_QUEUE", queue),
+        ):
+            payload = version_payload()
+        assert payload["latest"] == "fetching..."
+        assert payload["outdated"] is False
+        assert isinstance(queue.get_nowait(), CodexLatestVersionTask)
diff --git a/uv.lock b/uv.lock
index f4c6bdd68..8b2eddf26 100644
--- a/uv.lock
+++ b/uv.lock
@@ -133,49 +133,49 @@ wheels = [
 
 [[package]]
 name = "backports-zstd"
-version = "1.6.0"
+version = "1.7.0"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/8e/b5/5a873da082bd08acd6a497f7aae224e94a7c27fa8f24488089cc50a16c84/backports_zstd-1.6.0.tar.gz", hash = "sha256:80a7859ffe70bf239d7a2ce15293bdeb5b4280ff7dc326ffab312b0e254dbb24", size = 1000009, upload-time = "2026-06-14T10:50:58.555Z" }
-wheels = [
-    { url = "https://files.pythonhosted.org/packages/1e/bb/009af3a9532d4cc66d5385391c512210fae32ab2442605f26aca1d8d2957/backports_zstd-1.6.0-cp312-cp312-macosx_10_13_x86_64.whl", hash = "sha256:0466b14723f3b7697669c00ee66fe16e30e25636b286b0a923fa86fa3d8a753c", size = 437407, upload-time = "2026-06-14T10:49:50.155Z" },
-    { url = "https://files.pythonhosted.org/packages/0c/76/f7c02efde81ebb9993586f9e435d2fd1191a6f806f640e4eeb8d004493ed/backports_zstd-1.6.0-cp312-cp312-macosx_11_0_arm64.whl", hash = "sha256:1d146926e997d2d3de8212bdcbf4985344a2622ca3bec458d8908000a84fd883", size = 363519, upload-time = "2026-06-14T10:49:51.383Z" },
-    { url = "https://files.pythonhosted.org/packages/2e/5e/0cf66f12472fe3e082cc4134395a7e0b8746cfb30aabd74251ce8fafa9a7/backports_zstd-1.6.0-cp312-cp312-manylinux2010_i686.manylinux_2_12_i686.manylinux_2_28_i686.whl", hash = "sha256:460fd6b3f338c659507ae36cfd6b58ac9942a2ff233c5cf574416dfec0451a84", size = 507756, upload-time = "2026-06-14T10:49:52.497Z" },
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-    { url = "https://files.pythonhosted.org/packages/e3/75/f16b1d3e33ca396525847c81d96e3de7bc74d2c6f9ca2ddee76b0c450697/backports_zstd-1.6.0-cp312-cp312-manylinux2014_ppc64le.manylinux_2_17_ppc64le.manylinux_2_28_ppc64le.whl", hash = "sha256:beb43e9885202c8d4f3762319ed4d5e98e197622afbff8439fbbdd81d08938b9", size = 583029, upload-time = "2026-06-14T10:49:55.132Z" },
-    { url = "https://files.pythonhosted.org/packages/e1/2b/a17b111b631e1c79a0e570881c1a266c661b936585afa395435a458b1991/backports_zstd-1.6.0-cp312-cp312-manylinux2014_s390x.manylinux_2_17_s390x.manylinux_2_28_s390x.whl", hash = "sha256:fbb746522ebfc11155f1cd688e2c48ef3d74125e38b63eabdaab068a055c3e88", size = 641741, upload-time = "2026-06-14T10:49:56.42Z" },
-    { url = "https://files.pythonhosted.org/packages/6b/b2/d17b2722c636d64b4e77ddc68d8d0625719d39f94021be8719a218af4c0a/backports_zstd-1.6.0-cp312-cp312-manylinux2014_x86_64.manylinux_2_17_x86_64.manylinux_2_28_x86_64.whl", hash = "sha256:1a99710fbb225d459d66def4dc2bb2cd4a9a0bdc8b799fc0621cfdd863be9c93", size = 495554, upload-time = "2026-06-14T10:49:57.652Z" },
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