diff --git a/tools/windows/DatadogAgentInstaller/WixSetup/Datadog/AgentInstaller.cs b/tools/windows/DatadogAgentInstaller/WixSetup/Datadog/AgentInstaller.cs
index 77cce0e5231ea..d796af3d9c378 100644
--- a/tools/windows/DatadogAgentInstaller/WixSetup/Datadog/AgentInstaller.cs
+++ b/tools/windows/DatadogAgentInstaller/WixSetup/Datadog/AgentInstaller.cs
@@ -129,6 +129,14 @@ public Project ConfigureProject()
                 }
             );
 
+            // Ensures that the "change" dialog also reinstall the product.
+            project.AddAction(new SetPropertyAction("REINSTALL", "ALL")
+            {
+                Condition = Conditions.Maintenance,
+                When = When.After,
+                Step = Step.FindRelatedProducts
+            });
+
             // Conditionally include the PROCMON MSM while it is in active development to make it easier
             // to build/ship without it.
             if (!string.IsNullOrEmpty(Environment.GetEnvironmentVariable("WINDOWS_DDPROCMON_DRIVER")))
@@ -310,6 +318,15 @@ public Project ConfigureProject()
                         .First(x => x.HasAttribute("Id", value => value == "MainApplication"))
                         .AddElement("MergeRef", "Id=ddprocmoninstall");
                 }
+
+                // Configure the service when the parent Component is reinstalled
+                // This doesn't concerns the service permissions but the DelayedAutoStart, PreShutdownDelay etc...
+                document.FindAll("ServiceConfig")
+                    .Where(sc => sc.HasAttribute("OnReinstall"))
+                    .ForEach(sc => sc.SetAttributeValue("OnReinstall", "yes"));
+
+                // Always remove service, this will reset the service permissions.
+                document.FindSingle("DeleteServices").SetValue(Condition.Always);
             };
             project.WixSourceFormated += (ref string content) => WixSourceFormated?.Invoke(content);
             project.WixSourceSaved += name => WixSourceSaved?.Invoke(name);
@@ -402,7 +419,9 @@ private static ServiceInstaller GenerateServiceInstaller(string name, string dis
                 StopOn = null,
                 Start = SvcStartType.auto,
                 DelayedAutoStart = true,
-                RemoveOn = SvcEvent.Uninstall_Wait,
+                // Specifies that the service should be removed by the DeleteServices action on both install and uninstall.
+                // This ensures that if there is a (perhaps orphaned) service with the same name we remove it first.
+                RemoveOn = SvcEvent.InstallUninstall_Wait,
                 ServiceSid = ServiceSid.none,
                 FirstFailureActionType = FailureActionType.restart,
                 SecondFailureActionType = FailureActionType.restart,
@@ -437,7 +456,9 @@ private static ServiceInstaller GenerateDependentServiceInstaller(
                 // Tell MSI not to stop the services. We handle service stop manually in StopDDServices custom action.
                 StopOn = null,
                 Start = SvcStartType.demand,
-                RemoveOn = SvcEvent.Uninstall_Wait,
+                // Specifies that the service should be removed by the DeleteServices action on both install and uninstall.
+                // This ensures that if there is a (perhaps orphaned) service with the same name we remove it first.
+                RemoveOn = SvcEvent.InstallUninstall_Wait,
                 ServiceSid = ServiceSid.none,
                 FirstFailureActionType = FailureActionType.restart,
                 SecondFailureActionType = FailureActionType.restart,