Nine fixes from a review of the installer against its actual audience: DT leads
at sister sites who are not Windows, IIS or Python specialists and who will lean
on an AI assistant to get through it.
TRUTHFULNESS. The preflight was advisory - an operator read 'IIS is not
installed', pressed Next, answered five more pages and the install died partway
through with Python already on the box. The results page now blocks while
anything is failing, repaints on every run instead of latching after the first,
and offers 'Check again' so a fixed problem does not mean starting over. On
failure the wizard said 'Nothing was left running', which is false in every path
because the stages run with -OnFailure never: it now says the server is
part-configured, that re-running is safe, and how to remove it. The final page no
longer reads 'ShopDB-Flask is ready' after a failed install.
SECRETS. The generated MySQL root password went to Write-Host in a process the
wizard runs hidden - so nobody saw it - and stdout is forwarded into the setup
log operators are told to send to support, so it was permanently recorded for
everyone who did not need it. It now goes to an ACL'd file. Database dumps, which
contain every user password hash, landed in a ProgramData directory readable by
every user on the box; the directory is now locked at creation.
UPGRADES ON REMOTE-DATABASE SITES. mysqldump was looked for only under local
MySQL install paths, so a site whose database is on another host silently skipped
every pre-upgrade backup - after stage 2 had already stopped the pool and
replaced the tree. Find-MysqlTool now prefers a client shipped in the bundle,
stage 2 stages it onto the server, preflight reports when it is missing, and
mysqlclient\ is an optional locked payload.
UNINSTALL. A subpath install is an IIS Application, not a site; removing only the
site left the application pointing at a deleted directory, so the parent site -
at West Jefferson, the live classic ASP - served 503 on that path forever while
Add/Remove Programs reported success. Uninstall now reads MOUNT_PATH and removes
the application. The firewall rule was created as "$SiteName $SitePort" and
removed as the literal 'ShopDB-Flask 8090', which matches nothing.
DAY-2 TOOLING. Every shortcut now passes -AppRoot and -SitePort, and the console
forwards them through its own elevation and 32-bit relaunches instead of
discarding them - a non-default directory or port made it report a healthy site
as broken, from a shortcut the installer wrote. 'Open ShopDB-Flask' resolved to a
hardcoded localhost:8090 that was wrong for every subpath install; it now asks
the console, which reads the address the installer recorded, and no longer
demands administrator to open a browser.
SMOKE TEST. The parent-site port lookup filtered for an http binding and
defaulted to 80, so an https-only parent site failed a working install with a red
dialog.
DOCS AND /api/docs. The installer was invisible: nothing in docs/, README.md or
CLAUDE.md mentioned it, so a DT lead or their assistant landed on the manual IIS
runbook and hand-built the very server the installer then refuses to upgrade.
docs/INSTALL-WINDOWS.md and docs/OPERATE-WINDOWS.md are now the canonical route,
the two manual runbooks are bannered as reference-only, README and CLAUDE.md
route by target, and llms.txt tells an assistant which document to follow and to
ask for 'check -Json' before diagnosing. Both ship on the server, along with
openapi.json and llms.txt - without those the self-hosted /api/docs was broken on
every installed box, which matters most to the sites least able to debug it.
Stage 5 now checks it actually serves.
shopdb-admin.ps1 gains 'check -Json': one structured, secret-free block covering
version, publishing method, IIS state, HTTP reachability, database, Python
version, plugins and errors. That is the cheapest useful answer to 'the operator
will ask an LLM' - it works with no infrastructure, which a install-time MCP
server could not.
Stage 4 decided whether the IIS objects it was about to reconcile were its own by
testing for .installed-version. Stage 2 writes that file, and stage 2 always runs
first in a '-Stage all' install - so by the time the guard looked, the stamp it
had just written made every server look like one this installer built, including
the hand-built ones the guard exists to protect.
Stage 2 now records whether a stamp was present BEFORE it writes its own, and
stage 4 reads that observation. Running stage 4 alone still tests the file, which
is correct there: no stage 2 has run to disturb it.
Found by review, not by test - the guard has no coverage, because exercising it
needs a live IIS.
Two guards for a server deployed by hand, which the West Jefferson production
box is.
An existing venv is reused, which is right for a repair or an upgrade of an
install this made, and wrong when the venv belongs to a different Python. The
wheelhouse is tagged for one minor version, so pip finds no candidate for the
compiled packages and dies partway through - after Python has been installed and
the application tree replaced. The two versions are now compared up front and
the run stops with both numbers and what to do about it.
Switching deployment method removes the other method's IIS artifact. That is
correct when this installer owns both and dangerous when it does not: a wrong
-MountAlias would call Remove-WebApplication on a live mount with no prompt and
no error, and the first sign would be the site returning 404. It now refuses
unless a version stamp shows this installer made the install, or -AdoptExisting
is passed, and the refusal lists exactly what it would have removed.
IIS does not set X-Forwarded-For on its own and HttpPlatformHandler connects
from loopback, so without a rewrite rule every client reads as 127.0.0.1. The
GE-Enforce IP allowlist, the dashboard visitor-location lookup and per-host
login rate limiting all stop working, silently. The rule needed URL Rewrite,
which the installer told operators to download - from an air-gapped server.
URL Rewrite now ships in the bundle, and the wizard asks which case applies,
because the two answers are mutually exclusive. Directly exposed: install it and
set X-Forwarded-For from REMOTE_ADDR, which is what stops a client spoofing its
own. Behind a proxy: leave the rule off, since REMOTE_ADDR is the proxy and
applying it would discard the real client IP.
The rule is enabled by deleting two explicit marker lines rather than by a regex
over the surrounding comment, so editing that prose cannot silently disable it.
An existing web.config is no longer overwritten. It is the one file on a server
that legitimately carries hand-edits, and replacing it reverted them without a
word - on a server where the X-Forwarded-For rule had been enabled by hand, that
alone would have turned the GE-Enforce IP allowlist off. The installer reports
what it found instead.
pip now runs with --require-hashes and --only-binary=:all:. Hash-checking is
requested explicitly rather than inferred from the lockfile, so shipping an
unhashed requirements.txt fails loudly instead of quietly dropping the check.
shopdb-admin.ps1 gains a verify command: which bundle this server was installed
from, and whether the installed packages still match what shipped.
The .iss states its compiler floor. WizardStyle uses the built-in windows11
custom style, which needs Inno Setup 6.6.0; older compilers now fail with that
sentence rather than 'WizardStyle is invalid'.
Roughly 2500 lines of tested installer had been living in ~/Downloads and an
untracked folder - nothing was under version control.
It goes here rather than in a repo of its own because it depends on application
internals: the `flask plugin` verbs, site-profile.json, MOUNT_PATH, and the
plugin registry. Versioned separately it would drift out of step with the thing
it installs.
Contents: the read-only preflight, the staged installer (bundled MySQL, runtime,
schema, IIS, verify, uninstall), the operator console, the Inno Setup wizard, the
bundle builder and the artwork generator.
bundle/ and Output/ are ignored - regenerable, and ~220MB. plugins.iss is ignored
because build-installer.sh generates it from the staged payload. The artwork IS
committed so a Windows build box does not need Python and cairosvg.
Verified end to end on Windows Server 2025 against a bundled MySQL 8.0 and an
existing MySQL 5.6: fresh install, upgrade with backup and rollback, re-run
idempotency, uninstall, and both deployment methods including switching between
them. Not yet verified: a hypervisor-level air-gapped run, and any load from a
real browser (every HTTP check so far used curl, which sends no Origin header).
