shopdb-flask/deploy/windows/installer

Windows installer

Builds a single self-contained .exe that installs ShopDB-Flask on an air-gapped Windows Server. Nothing here ever touches the network at install time: Python, the wheels, the SPA and (optionally) MySQL all ship inside it.

Lives with the application on purpose. The installer depends on app internals - flask plugin verbs, site-profile.json, MOUNT_PATH, the plugin registry - so a separate repo would drift out of step with the thing it installs.

Files

File	What it is
shopdb-preflight.ps1	Stage 1. Read-only. Changes nothing, reports what this server is missing.
shopdb-install.ps1	Stages 0 and 2-5 plus uninstall. All the actual work.
shopdb-admin.ps1	Operator console installed alongside the app: status, restart, logs, backup, plugins.
ShopDBFlask.iss	Inno Setup wizard. A thin wrapper - it collects input and runs the stages.
build-installer.sh	Stages the bundle from a site profile.
make-branding.py	Generates wizard artwork and the icon from frontend/public/*.svg.
*.bmp, shopdb.ico	Generated artwork, committed so a Windows build box needs no Python.
build-installer.ps1	The same build, natively on Windows. No Bash needed.
bundle-lock.json	The exact third-party payload this installer ships. Reviewed by commit.
bundle-lock.ps1	Creates and checks that lock. Also runs on the target server.
refresh-bundle-lock.ps1	Regenerates the lock, after showing what changed.
verify_bundle_lock.py	The same check for the Bash builder, so Linux needs no pwsh.

Building

Two builders, same result. Use whichever machine you are on - build-installer.ps1 does the whole job natively so a Windows work PC needs no Bash.

# Linux / WSL
./build-installer.sh ../../site-profile.example.json

# Windows
.\build-installer.ps1 -Profile ..\..\site-profile.example.json

Both stage the app tree, build the SPA twice, write plugins.iss, copy the installer scripts from this directory, and then verify the third-party payload against bundle-lock.json. They exit non-zero if it does not match.

The payload itself is added by hand, and no longer needs Windows to produce:

bundle/wheels/               pip download -r requirements.txt --only-binary=:all: \
                               --platform win_amd64 --python-version 314 \
                               --implementation cp --abi cp314 -d wheels
bundle/python/               python-3.14.x-amd64.exe
bundle/httpplatformhandler/  httpPlatformHandler_amd64.msi
bundle/urlrewrite/           rewrite_amd64.msi        (client-IP rule; see below)
bundle/vcredist/             VC_redist.x64.exe        (MySQL will not install without it)
bundle/mysql/                mysql-8.4.x-winx64.msi   (bundled-database option only)
bundle/mysqlclient/          mysql.exe, mysqldump.exe + libcrypto/libssl (backups)

Then compile on Windows:

iscc ShopDBFlask.iss

Inno Setup 6.6.0 or newer. The wizard uses the built-in windows11 custom style, which earlier versions reject. The script fails at compile time with that sentence rather than with a bare "WizardStyle is invalid".

The wheelhouse is cp314-locked. A different Python minor version means a different wheelhouse; the installer will not use a Python it did not install.

What is pinned, and where

Three layers, because no one of them covers the whole problem.

Layer	Covers	Enforced
requirements.txt sha256 per package	every wheel is genuinely what upstream published	pip --require-hashes at install; aborts on mismatch
bundle-lock.json	the EXACT payload: wheels, Python installer, MSIs	both builders, and again on the server before anything runs
git	the application tree	code review

--require-hashes alone is not enough. pip lists every artifact of a pinned version - cffi 2.1.0 has 100 hashes - so it proves the wheel is genuine, not that it is the wheel this bundle was built and tested with. It also ignores extra files in the wheelhouse, and says nothing about the Python installer or the MSIs, all of which run as SYSTEM on the target server.

So bundle-lock.json records an exact file set with a sha256 and a byte size each, and verification is set equality: a missing file, an unexpected extra file, or changed content all fail. There is no install-time override.

The lockfile is --universal, so one file serves Linux (dev, Docker, CI) and the Windows wheelhouse. A Linux-only resolve had silently omitted colorama, a win32-only dependency of click - which in hash-checking mode is a hard error rather than a quiet omission.

Verifying the installer itself

bundle-lock.json is inside the thing it describes, so it proves the payload was not altered between build and install - not that the .exe you received is the one that was built. That needs something out of band. Two options, in order of preference:

1. Authenticode-sign the .exe with a GE code-signing certificate. Windows then shows a real publisher instead of "Unknown", which is also what stops an operator learning to click through the SmartScreen warning.
2. Publish a sha256 per release through a different channel than the file itself, and have the receiving site check it: Get-FileHash ShopDBFlask_Installer_*.exe -Algorithm SHA256

Neither is wired up yet. Until one is, an installer is only as trustworthy as the share it arrived on.

Changing what ships

.\refresh-bundle-lock.ps1        # show what changed, write nothing
.\refresh-bundle-lock.ps1 -Yes   # write it

Then commit bundle-lock.json. That commit is the review - it is the only place a change to what runs as SYSTEM on a customer's server becomes visible to a human. refresh-bundle-lock.ps1 refuses to overwrite an existing lock until you have seen the diff, for that reason.

To stage a bundle before its lock exists: ALLOW_UNLOCKED=1 (Bash) or -AllowUnlocked (PowerShell). Bundles built that way must not be shipped.

Verifying a live server, months later and offline:

shopdb-admin.ps1 verify

Servers this installer did not build

It is built for greenfield: its own Python, its own venv, its own IIS objects. Its upgrade path assumes the thing being upgraded came out of a previous run. Two guards keep it from damaging a server that was deployed by hand.

Python minor version. An existing venv is reused, which is right for a repair or an upgrade. It is wrong when the venv belongs to a different Python - the wheelhouse is tagged for one minor version, so pip would die at the first compiled package, after Python was installed and the app tree replaced. The installer compares the two up front and stops with both version numbers.

IIS objects. Switching deployment method removes the other method's artifact, which is correct when the installer owns both and dangerous when it does not: a wrong -MountAlias would delete a live mount with no prompt. It now refuses unless there is a version stamp proving it made the install, or you pass -AdoptExisting. The refusal lists exactly what it would have removed.

An existing web.config is never overwritten in either case.

For the West Jefferson production server specifically, this is a migration, not an upgrade - prod runs Python 3.13 against a hand-built deployment, so it needs a deliberate window, a database backup, and web.config reconciled by hand.

Bill of materials

Every build stages a CycloneDX 1.6 SBOM at sbom.cdx.json, inside the application tree, so it installs onto the server with the app. Both ecosystems, in one document:

• Python - every pin in requirements.txt, with the sha256 the installer enforces. Environment markers are ignored: a sys_platform == 'win32' dependency still installs on the target.
• npm - every package in frontend/package-lock.json. Build-only packages are marked scope: excluded rather than dropped, so "not here" is distinguishable from "not looked for".

It ships to the server because an air-gapped site cannot be scanned from anywhere else. When a CVE lands, the answer is already on the box:

shopdb-admin.ps1 verify                 # counts, and which bundle this is
shopdb-admin.ps1 verify -Path leaflet   # is that component here, at what version

Generated by scripts/generate_sbom.py from files that are already pinned and committed, so it is a translation rather than a scan - no network, no extra toolchain on the build box, and byte-identical output for the same inputs. It is deliberately not in bundle-lock.json: its provenance is git, not the payload.

Client IP addresses

IIS does not set X-Forwarded-For on its own, and HttpPlatformHandler connects from loopback. Without a rule, every client reads as 127.0.0.1 - so the GE-Enforce IP allowlist, the dashboard's visitor-location lookup and per-host login rate limiting all stop working, silently.

The wizard asks, because the two answers are mutually exclusive:

• Clients connect directly (-ClientIpSource direct, the default) - installs URL Rewrite from the bundle and sets X-Forwarded-For from REMOTE_ADDR. Overwriting the header is what stops a client spoofing its own.
• A proxy sits in front (-ClientIpSource proxy) - leaves the rule off. Behind ARR or a load balancer REMOTE_ADDR is the proxy, so applying the rule would discard the real client IP.

An existing web.config is never overwritten - it is the one file on a server that legitimately carries hand-edits. The installer reports what it found instead.

Deployment methods

Chosen in the wizard, and the bundle carries a SPA build for each because Vite compiles the base path in - it cannot be switched at install time.

• Its own site on a port (default 8090).
• Subpath under an existing site, e.g. http://<server-fqdn>/shopdb/. Needs no new DNS record. Three things must agree - the IIS application alias, MOUNT_PATH in .env, and the SPA's build-time base - so the alias is fixed per bundle (SUBPATH_ALIAS, default shopdb) and the installer refuses if the bundle's build does not match what was asked for.

Switching between methods removes the other one's IIS artifact and reconciles MOUNT_PATH and CORS_ORIGINS, so a server never ends up with both.

Upgrades

Run a newer installer over an existing install. It:

• backs the database up first, verifies the dump is complete, and refuses to migrate if it cannot;
• restores from that backup if migrations fail, and reports honestly that DDL the failed migration committed cannot be undone;
• refuses to run a bundle older than what is installed;
• keeps .env unless new credentials are supplied, and copies it aside first;
• stops the app pool before replacing files, then starts it again.

Whether a run is an upgrade is decided by probing the target database, not by whether the app directory exists - a rebuilt server pointed at an existing database is an upgrade, and treating it as fresh would drop tables.

Testing notes

Verified end to end on Windows Server 2025 against both a bundled MySQL 8.4 LTS and an existing MySQL 5.6: fresh install, upgrade, re-run idempotency, failure and rollback, uninstall, and both deployment methods including switching between them.

Not yet verified: a fully air-gapped run with the network disabled at the hypervisor, and any load in a real browser (all HTTP checks so far used curl, which sends no Origin header - so CORS_ORIGINS is untested in anger).