shopdb-flask/docs/INSTALL-WINDOWS-IIS.md

ShopDB - Windows + IIS install runbook

Not the route for a new site. Sister sites install from the Windows installer - one .exe, no manual IIS work: INSTALL-WINDOWS.md.

This document is the manual procedure, kept for reference and for hand-built servers that predate the installer. Note that the installer will not adopt a server built this way without -AdoptExisting, on purpose.

A step-by-step, tested install for a new site on Windows Server / Windows 11 with IIS in front of the Flask app (HttpPlatformHandler -> waitress), backed by MySQL. This runbook was validated end to end on a win11 + IIS + MySQL 5.6 box.

APP_ROOT below = the deploy folder, e.g. C:\shopdb-flask (where wsgi.py lives). Run PowerShell as Administrator.

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0. Prerequisites

Need	Notes
Python 3.14 (64-bit)	python --version
IIS with HttpPlatformHandler	https://www.iis.net/downloads/microsoft/httpplatformhandler (direct MSI: download.microsoft.com/download/8/1/3/813AC4E6-9203-4F7A-8DD5-F3D54D10C5CD/httpPlatformHandler_amd64.msi)
MySQL 8.4 LTS (standard for new installs)	reachable from the app host. 8.0 reached end of life in April 2026 and no longer ships a standalone server MSI. 5.7+ still works on an existing server; 5.6 needs the flags in step 1.
URL Rewrite (optional)	only for the real-client-IP rule; skip it and the app still runs

The app itself pulls in waitress and tzdata from requirements.txt (step 4).

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1. MySQL: flags (5.6 only) + database + user

On MySQL 5.6 only, add to my.ini/my.cnf under [mysqld] and restart MySQL (5.7+/8.0 need none of this):

innodb_file_per_table = 1
innodb_file_format    = Barracuda
innodb_large_prefix   = 1

Without them, flask db upgrade fails with error 1071 ("key too long") - the migrations use ROW_FORMAT=DYNAMIC, which needs the 3072-byte prefix these unlock.

Then create the database (utf8mb4) and an app user:

CREATE DATABASE shopdb_flask CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci;
CREATE USER 'shopdb'@'%' IDENTIFIED BY 'CHANGE_ME';
GRANT ALL PRIVILEGES ON shopdb_flask.* TO 'shopdb'@'%';
FLUSH PRIVILEGES;

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2. Deploy the app files

Copy the release (the repo minus venv/, .git/, node_modules/, frontend/src/) to APP_ROOT. It must contain wsgi.py, shopdb/, plugins/, migrations/, requirements.txt, and the pre-built frontend/dist/.

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3. Virtual env + dependencies

cd APP_ROOT
python -m venv venv
venv\Scripts\python -m pip install -r requirements.txt

This installs Flask, SQLAlchemy, PyMySQL, waitress (the WSGI server IIS launches) and tzdata (Windows has no IANA tz database; without it the notifications plugin fails with "No time zone found with key America/New_York").

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4. Secrets + connection (.env)

Create APP_ROOT\.env (read by wsgi.py via load_dotenv()). Lock its ACLs to the app-pool identity + admins.

FLASK_ENV=production
SECRET_KEY=<64+ random chars>
JWT_SECRET_KEY=<another 64+ random chars>
DATABASE_URL=mysql+pymysql://shopdb:CHANGE_ME@<mysql-host>:3306/shopdb_flask?charset=utf8mb4
CORS_ORIGINS=http://<the site's own hostname-or-ip:port>

Generate a key: venv\Scripts\python -c "import secrets;print(secrets.token_urlsafe(64))". Production refuses to boot if any of SECRET_KEY, JWT_SECRET_KEY, DATABASE_URL, CORS_ORIGINS is missing or a dev default.

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5. Preflight (catch problems before installing)

$env:FLASK_APP="shopdb"
venv\Scripts\flask db-utils preflight

Checks Python, required env, DB connectivity, and the MySQL 5.6 index flags, and prints exactly what to fix. Fix any FAIL before continuing.

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6. Schema + data + plugins + admin

$env:FLASK_APP="shopdb"

venv\Scripts\flask db upgrade                # creates every table (to head)
venv\Scripts\flask seed reference-data       # statuses, machine/location/rel types
venv\Scripts\flask seed permissions
venv\Scripts\flask seed settings

# enable the plugins this site tracks (registry is empty on a fresh box).
# usb + employees install DISABLED by default - enable them later in the wizard
# if the site wants those (they create extra tables).
foreach ($p in "computers","machines","network","notifications","printers","knowledgebase","slides","warranty") {
  venv\Scripts\flask plugin install $p
}

# first admin (password generated + printed once - store it):
venv\Scripts\flask seed admin --username admin --email admin@yourfacility.example.com

Prefer no CLI? Skip seed admin (and even the seed steps): start the site, and the login page offers to create the first admin on a fresh instance, then the setup wizard can seed reference data. Either path works.

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7. IIS site

Two supported deployment methods:

• Method A - own site (recommended, default): the app gets its own IIS site, port (or hostname), app pool, and venv. Steps 1-5 below.
• Method B - subpath under an existing site: the app runs as an IIS Application (e.g. /ops) under a site you already have (such as the classic ASP site or Default Web Site), so it shares that site's binding and TLS cert: https://<host>/ops/. Do steps 1-4 below, then follow 7b instead of step 5.

1. Copy deploy\windows\web.config to APP_ROOT\web.config. If APP_ROOT is not C:\shopdb-flask, fix the paths inside it. Create APP_ROOT\logs.
2. Create an app pool with No Managed Code:

   Import-Module WebAdministration
   New-WebAppPool -Name shopdbflask
   Set-ItemProperty IIS:\AppPools\shopdbflask -Name managedRuntimeVersion -Value ""
   

3. Grant the app-pool identity access:

   icacls APP_ROOT /grant "IIS AppPool\shopdbflask:(OI)(CI)RX" /T
   icacls APP_ROOT\logs /grant "IIS AppPool\shopdbflask:(OI)(CI)M" /T
   mkdir APP_ROOT\instance 2>NUL
   icacls APP_ROOT\instance /grant "IIS AppPool\shopdbflask:(OI)(CI)M" /T
   

4. Unlock the handler sections (locked server-wide by default; without this IIS returns HTTP 500.19):

   %windir%\system32\inetsrv\appcmd unlock config /section:system.webServer/handlers
   %windir%\system32\inetsrv\appcmd unlock config /section:system.webServer/httpPlatform
   

5. Create the site (own port; the classic ASP site can keep 8080):

   New-Website -Name shopdb-flask -Port 8090 -PhysicalPath APP_ROOT -ApplicationPool shopdbflask
   New-NetFirewallRule -DisplayName "shopdb-flask 8090" -Direction Inbound -Protocol TCP -LocalPort 8090 -Action Allow
   Start-Website shopdb-flask
   

IIS launches waitress-serve --port=%HTTP_PLATFORM_PORT% wsgi:app per the web.config and reverse-proxies the site port to it. First request takes ~15s (the app boots + connects to MySQL).

7b. Method B: subpath under an existing site

The mount path must match in three places: the IIS Application alias, the MOUNT_PATH the backend sees, and the VITE_BASE_PATH the frontend was built with. /ops is the example throughout; any alias works.

1. Rebuild the frontend for the subpath (on the dev box, then copy dist):

   cd frontend && VITE_BASE_PATH=/ops/ npm run build     # note the trailing slash
   

2. Create the Application under the existing site (instead of New-Website):

   New-WebApplication -Site "Default Web Site" -Name ops -PhysicalPath APP_ROOT -ApplicationPool shopdbflask
   

3. Tell the backend its mount path: in APP_ROOT\web.config, uncomment the MOUNT_PATH environment variable (value /ops), or set MOUNT_PATH=/ops in APP_ROOT\.env. wsgi.py then serves everything under the prefix (requests outside it get a plain 404 naming the mount).
4. Recycle the app pool. The app is at http(s)://<host>/ops/ and the API at /ops/api/....

The handler mappings in the app's web.config apply only inside the Application, so the parent site's own handlers (classic ASP, static files) are untouched. CORS_ORIGINS in .env is origin-only (scheme + host + port, no path), so it is the same for both methods.

The X-Forwarded-For URL Rewrite rule in web.config is commented out by default. It needs the URL Rewrite module; with it active but the module absent, IIS returns 500.19. Install URL Rewrite, then uncomment the <rewrite> block, to record real client IPs in audit logs.

Two companion requirements, or the app keeps seeing 127.0.0.1: allowedServerVariables is locked at server level by default (500.52 when the block activates) - unlock once with appcmd unlock config -section:system.webServer/rewrite/allowedServerVariables. And waitress 2+ strips X-Forwarded-For from untrusted proxies, so the waitress arguments line must carry --trusted-proxy=127.0.0.1 --trusted-proxy-headers=x-forwarded-for (the shipped web.config already does).

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8. Smoke test + first run

(Invoke-WebRequest http://localhost:8090/ -UseBasicParsing).StatusCode      # 200 (SPA)
Invoke-WebRequest http://localhost:8090/api/auth/login -Method POST `
  -Body '{"username":"admin","password":"<the printed password>"}' `
  -ContentType application/json -UseBasicParsing                            # 200 + token

Browse to http://<host>:8090, sign in as the admin, and the setup wizard walks through site name, features (per-plugin: create tables here vs connect a DB), floor-map upload, and starter data. Multiple Flask apps can share one IIS box - each gets its own site, app pool, port, and venv.

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Troubleshooting

Symptom	Cause / fix
flask db upgrade -> error 1071	MySQL 5.6 without the step-1 flags (or server not restarted).
IIS 500.19	handler sections not unlocked (step 7.4), or the <rewrite> block active without URL Rewrite.
IIS 500.52 after enabling the rewrite block	allowedServerVariables locked at server level - appcmd unlock config -section:system.webServer/rewrite/allowedServerVariables.
Audit log shows only 127.0.0.1 with the rewrite block active	waitress strips untrusted proxy headers - --trusted-proxy=127.0.0.1 --trusted-proxy-headers=x-forwarded-for missing from the waitress arguments.
500 with an empty HttpPlatform log	app-pool identity can't read APP_ROOT / run the venv (step 7.3), or .env missing/invalid.
"internal error" toggling plugins, or uploads fail	app pool cannot WRITE APP_ROOT\instance (plugin registry, logos, photos, files live there) - step 7.3 grants it Modify.
"No time zone found with key America/New_York"	tzdata not installed (pip install tzdata).
Nav missing Machines/PCs/...	plugins not installed (step 6 flask plugin install), or site not recycled.
Method B: blank page / assets 404 under /ops	frontend dist built without VITE_BASE_PATH=/ops/ (step 7b.1).
Method B: SPA loads but every API call 404s	MOUNT_PATH unset or not matching the Application alias (step 7b.3).
ConfigError on boot	a required .env var missing or left at a dev default.