From 23984040bedd7d487166914c287e27309dcd0725 Mon Sep 17 00:00:00 2001
From: Daniel Covington <danielc@kentcommunications.com>
Date: Mon, 24 Aug 2026 12:40:57 -0400
Subject: [PATCH] Fix deploy: wait for app pools to actually stop before wiping
 RemoteDir

Stop-WebAppPool only requests a stop - the w3wp.exe worker process can
keep running for a few seconds afterwards, still holding the site's
files open, so the previous fix (stopping both sites before the wipe)
wasn't sufficient on its own.

- Wait-AppPoolFullyStopped: polls app pool state until Stopped (30s
  timeout), then force-kills any lingering w3wp.exe for that pool
- Remove-DirectoryContentsWithRetry: retries the wipe a few times with
  a short delay, since file handles can take a moment to release even
  after the worker process is confirmed gone
---
 scripts/deploy-iis-remote-apply.ps1 | 51 ++++++++++++++++++++++++++++-
 1 file changed, 50 insertions(+), 1 deletion(-)

diff --git a/scripts/deploy-iis-remote-apply.ps1 b/scripts/deploy-iis-remote-apply.ps1
index 3a512dc..28eef32 100644
--- a/scripts/deploy-iis-remote-apply.ps1
+++ b/scripts/deploy-iis-remote-apply.ps1
@@ -25,6 +25,53 @@ param(
 $ErrorActionPreference = 'Stop'
 Import-Module WebAdministration
 
+# Stop-WebAppPool only requests a stop - the w3wp.exe worker process can keep running for a
+# few seconds afterwards (finishing in-flight requests), still holding the site's files open.
+# Wait for the pool to actually report Stopped, then force-kill any worker process that's
+# still lingering past the timeout so the wipe below doesn't hit "Access is denied".
+function Wait-AppPoolFullyStopped {
+  param([string]$PoolName, [int]$TimeoutSec = 30)
+
+  if([string]::IsNullOrWhiteSpace($PoolName)){ return }
+
+  $deadline = (Get-Date).AddSeconds($TimeoutSec)
+  while((Get-Date) -lt $deadline){
+    if((Get-WebAppPoolState -Name $PoolName -ErrorAction SilentlyContinue).Value -eq 'Stopped'){
+      return
+    }
+    Start-Sleep -Milliseconds 500
+  }
+
+  Write-Host "App pool $PoolName did not report Stopped within ${TimeoutSec}s - killing any lingering worker process"
+  Get-CimInstance Win32_Process -Filter "Name = 'w3wp.exe'" -ErrorAction SilentlyContinue |
+    Where-Object { $_.CommandLine -like ('*' + $PoolName + '*') } |
+    ForEach-Object {
+      try { Stop-Process -Id $_.ProcessId -Force -ErrorAction SilentlyContinue } catch { }
+    }
+}
+
+# Wipes are attempted a few times with a short pause - file handles (IIS or AV scanning
+# the just-stopped worker process's files) can take a moment to release even after the
+# worker process itself is confirmed gone.
+function Remove-DirectoryContentsWithRetry {
+  param([string]$Path, [int]$MaxAttempts = 5, [int]$DelayMs = 2000)
+
+  for($attempt = 1; $attempt -le $MaxAttempts; $attempt++){
+    $failure = $null
+    try {
+      Remove-Item -Recurse -Force $Path -ErrorAction Stop
+      return
+    } catch {
+      $failure = $_
+      if($attempt -lt $MaxAttempts){
+        Write-Host "Wipe attempt $attempt failed (files still locked?) - retrying in $($DelayMs)ms"
+        Start-Sleep -Milliseconds $DelayMs
+      }
+    }
+  }
+  throw $failure
+}
+
 if(!(Get-Website -Name $SiteName -ErrorAction SilentlyContinue)){
   throw "IIS site '$SiteName' does not exist yet. Create the site and app pool once manually (or via a one-time setup script) before running this deploy."
 }
@@ -35,6 +82,7 @@ if(!(Test-Path ('IIS:\AppPools\' + $AppPool))){
 Write-Host "Stopping IIS site $SiteName and app pool $AppPool"
 try { Stop-Website -Name $SiteName } catch { }
 try { Stop-WebAppPool -Name $AppPool } catch { }
+Wait-AppPoolFullyStopped -PoolName $AppPool
 
 # The admin site's physical path may already point inside RemoteDir (e.g. RemoteDir\public-admin)
 # from a previous deploy - if it's left running, IIS holds those files open and the wipe below
@@ -44,12 +92,13 @@ if(![string]::IsNullOrWhiteSpace($AdminSiteName) -and (Get-Website -Name $AdminS
   try { Stop-Website -Name $AdminSiteName } catch { }
   if(![string]::IsNullOrWhiteSpace($AdminAppPool)){
     try { Stop-WebAppPool -Name $AdminAppPool } catch { }
+    Wait-AppPoolFullyStopped -PoolName $AdminAppPool
   }
 }
 
 if(Test-Path $RemoteDir){
   Write-Host "Wiping $RemoteDir"
-  Remove-Item -Recurse -Force (Join-Path $RemoteDir '*') -ErrorAction SilentlyContinue
+  Remove-DirectoryContentsWithRetry -Path (Join-Path $RemoteDir '*')
 } else {
   New-Item -ItemType Directory -Force -Path $RemoteDir | Out-Null
 }