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](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.

---

## 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).

---

## 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:

```sql
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;
```

---

## 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/`.

---

## 3. Virtual env + dependencies

```powershell
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").

---

## 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.

---

## 5. Preflight (catch problems before installing)

```powershell
$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.

---

## 6. Schema + data + plugins + admin

```powershell
$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
}

# EVERY plugin owns its own Alembic chain (ADR-008), and `flask db upgrade`
# above ran only the core one. Skipping this is how a new column reaches
# production as a 1054 "Unknown column" error on the page that uses it.
venv\Scripts\flask plugin upgrade-all

# 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.

---

## 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**:
   ```powershell
   Import-Module WebAdministration
   New-WebAppPool -Name shopdbflask
   Set-ItemProperty IIS:\AppPools\shopdbflask -Name managedRuntimeVersion -Value ""
   ```
3. Grant the app-pool identity access:
   ```powershell
   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**):
   ```powershell
   %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):
   ```powershell
   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`):
   ```bash
   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`):
   ```powershell
   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).

---

## 8. Smoke test + first run

```powershell
(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.

---

## Redeploying a hand-built server

A hand-built server has no installer to run, so an update is done by hand in the
same order the installer would:

1. Copy the new code to the application root, rebuilding `frontend/dist` first
   if the UI changed.
2. `venv\Scripts\pip install -r requirements.txt`, if dependencies changed.
3. `venv\Scripts\flask db upgrade` for the core chain, then
   `venv\Scripts\flask plugin upgrade-all` for the plugin chains. Both, every
   time - the second is the one people skip, and it surfaces days later as a
   1054 "Unknown column".
4. Recycle the application pool.

Take a database backup before step 3. The installer does this automatically and
restores from it when a migration fails; by hand, it is yours to remember.

## 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. |