diff --git a/ee/maintained-apps/outputs/bitwarden/windows.json b/ee/maintained-apps/outputs/bitwarden/windows.json
index d9ba6a9f7e..947cabf2f1 100644
--- a/ee/maintained-apps/outputs/bitwarden/windows.json
+++ b/ee/maintained-apps/outputs/bitwarden/windows.json
@@ -1,15 +1,15 @@
 {
   "versions": [
     {
-      "version": "2026.4.0",
+      "version": "2026.5.0",
       "queries": {
         "exists": "SELECT 1 FROM programs WHERE name = 'Bitwarden' AND publisher = 'Bitwarden Inc.';",
-        "patched": "SELECT 1 WHERE NOT EXISTS (SELECT 1 FROM programs WHERE name = 'Bitwarden' AND publisher = 'Bitwarden Inc.' AND version_compare(version, '2026.4.0') < 0);"
+        "patched": "SELECT 1 WHERE NOT EXISTS (SELECT 1 FROM programs WHERE name = 'Bitwarden' AND publisher = 'Bitwarden Inc.' AND version_compare(version, '2026.5.0') < 0);"
       },
-      "installer_url": "https://github.com/bitwarden/clients/releases/download/desktop-v2026.4.0/Bitwarden-Installer-2026.4.0.exe",
+      "installer_url": "https://github.com/bitwarden/clients/releases/download/desktop-v2026.5.0/Bitwarden-Installer-2026.5.0.exe",
       "install_script_ref": "234a3679",
       "uninstall_script_ref": "365a2ac0",
-      "sha256": "e50063b68acb83362e07dd6a2a7e5a8c9e909d1146ea4420328505c71ffa6af8",
+      "sha256": "d07537695f14d7dd66f2f58304b39b8a8376b70c935b928812feacce3aacb7db",
       "default_categories": [
         "Productivity"
       ]
diff --git a/ee/maintained-apps/outputs/cryptomator/windows.json b/ee/maintained-apps/outputs/cryptomator/windows.json
index 9706bca38d..ce57009f23 100644
--- a/ee/maintained-apps/outputs/cryptomator/windows.json
+++ b/ee/maintained-apps/outputs/cryptomator/windows.json
@@ -18,6 +18,6 @@
   ],
   "refs": {
     "86999c6b": "# Fleet uninstalls app by finding all related product codes for the specified upgrade code\n$inst = New-Object -ComObject \"WindowsInstaller.Installer\"\n$timeoutSeconds = 300  # 5 minute timeout per product\n\nforeach ($product_code in $inst.RelatedProducts('{BDA45523-42B1-4CAE-9354-A45475ED4775}')) {\n    $process = Start-Process msiexec -ArgumentList @(\"/quiet\", \"/x\", $product_code, \"/norestart\") -PassThru\n    \n    # Wait for process with timeout\n    $completed = $process.WaitForExit($timeoutSeconds * 1000)\n    \n    if (-not $completed) {\n        Stop-Process -Id $process.Id -Force -ErrorAction SilentlyContinue\n        Exit 1603  # ERROR_UNINSTALL_FAILURE\n    }\n    \n    # If the uninstall failed, bail\n    if ($process.ExitCode -ne 0) {\n        Write-Output \"Uninstall for $($product_code) exited $($process.ExitCode)\"\n        Exit $process.ExitCode\n    }\n}\n\n# All uninstalls succeeded; exit success\nExit 0\n",
-    "8959087b": "$logFile = \"${env:TEMP}/fleet-install-software.log\"\n\ntry {\n\n$installProcess = Start-Process msiexec.exe `\n  -ArgumentList \"/quiet /norestart /lv ${logFile} /i `\"${env:INSTALLER_PATH}`\"\" `\n  -PassThru -Wait\n\nGet-Content $logFile -Tail 500\n\nExit $installProcess.ExitCode\n\n} catch {\n  Write-Host \"Error: $_\"\n  Exit 1\n}\n"
+    "8959087b": "$logFile = \"${env:TEMP}/fleet-install-software.log\"\n\ntry {\n\n$installProcess = Start-Process msiexec.exe `\n  -ArgumentList \"/quiet /norestart /lv ${logFile} /i `\"${env:INSTALLER_PATH}`\"\" `\n  -PassThru -Verb RunAs -Wait\n\nGet-Content $logFile -Tail 500\n\nExit $installProcess.ExitCode\n\n} catch {\n  Write-Host \"Error: $_\"\n  Exit 1\n}\n"
   }
 }