From 097114e8f5619e2292c5ece30f424582a55a7285 Mon Sep 17 00:00:00 2001
From: Marcos Oviedo <marcos@fleetdm.com>
Date: Thu, 23 Nov 2023 12:29:40 -0300
Subject: [PATCH] Fix windows installer orbit delete pending (#15301)

Relates to #14958

If some of the following don't apply, delete the relevant line.

<!-- Note that API documentation changes are now addressed by the
product design team. -->

- [X] Changes file added for user-visible changes in `changes/` or
`orbit/changes/`.
See [Changes
files](https://fleetdm.com/docs/contributing/committing-changes#changes-files)
for more information.
- [ ] Manual QA for all new/changed functionality
  - For Orbit and Fleet Desktop changes:
- [X] Manual QA must be performed in the three main OSs, macOS, Windows
and Linux.
- [ ] Auto-update manual QA, from released version of component to new
version (see [tools/tuf/test](../tools/tuf/test/README.md)).
---
 ...sue-14958-installer-windows-delete-pending |  1 +
 orbit/pkg/packaging/windows_templates.go      | 28 ++++++++++++++++++-
 2 files changed, 28 insertions(+), 1 deletion(-)
 create mode 100644 changes/issue-14958-installer-windows-delete-pending

diff --git a/changes/issue-14958-installer-windows-delete-pending b/changes/issue-14958-installer-windows-delete-pending
new file mode 100644
index 0000000000..a90bea43ec
--- /dev/null
+++ b/changes/issue-14958-installer-windows-delete-pending
@@ -0,0 +1 @@
+* Fixes delete pending issue on orbit.exe during installation
diff --git a/orbit/pkg/packaging/windows_templates.go b/orbit/pkg/packaging/windows_templates.go
index a2d25049bd..7d7d1a8be7 100644
--- a/orbit/pkg/packaging/windows_templates.go
+++ b/orbit/pkg/packaging/windows_templates.go
@@ -159,10 +159,36 @@ var windowsWixTemplate = template.Must(template.New("").Option("missingkey=error
                   Return="check"
                   Impersonate="no" />                    
 
+   <SetProperty Id="CA_WaitOrbit"
+                 Before ="CA_WaitOrbit"
+                 Sequence="execute"
+                 Value='&quot;[POWERSHELLEXE]&quot; -NoLogo -NonInteractive -NoProfile -ExecutionPolicy Bypass Wait-Process -Name orbit -Timeout 30 -ErrorAction SilentlyContinue' />
+
+    <CustomAction Id="CA_WaitOrbit"
+                  BinaryKey="WixCA"
+                  DllEntry="WixQuietExec64"
+                  Execute="deferred"
+                  Return="ignore"
+                  Impersonate="no" />
+
+   <SetProperty Id="CA_RemoveRebootPending"
+                 Before ="CA_RemoveRebootPending"
+                 Sequence="execute"
+                 Value='&quot;[POWERSHELLEXE]&quot; -NoLogo -NonInteractive -NoProfile -ExecutionPolicy Bypass Remove-Item -Path "$Env:Programfiles\orbit\bin" -Recurse -Force' />
+
+    <CustomAction Id="CA_RemoveRebootPending"
+                  BinaryKey="WixCA"
+                  DllEntry="WixQuietExec64"
+                  Execute="deferred"
+                  Return="ignore"
+                  Impersonate="no" />
+
     <InstallExecuteSequence>
       <Custom Action='CA_RemoveOrbit' Before='RemoveFiles'>(NOT UPGRADINGPRODUCTCODE) AND (REMOVE="ALL")</Custom> <!-- Only happens during uninstall -->
       <Custom Action='CA_UninstallOsquery' After='InstallFiles'>NOT Installed AND NOT WIX_UPGRADE_DETECTED</Custom> <!-- Only happens during first install -->
-      <Custom Action='CA_UpdateSecret' Before='InstallServices'>NOT Installed</Custom> <!-- It happens just before service creation -->      
+      <Custom Action='CA_UpdateSecret' Before='InstallServices'>NOT Installed</Custom> <!-- It happens just before service creation -->
+      <Custom Action="CA_WaitOrbit" Before="CA_RemoveRebootPending"/>
+      <Custom Action="CA_RemoveRebootPending" Before='InstallFiles'>NOT Installed</Custom> <!-- It removes reboot pending Orbit files -->
     </InstallExecuteSequence>
 
     <Feature Id="Orbit" Title="Fleet osquery" Level="1" Display="hidden">