diff --git a/Misc/NEWS b/Misc/NEWS
index 697ddb02345..2dc4d9b9a0b 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -437,6 +437,9 @@ Build
 Windows
 -------
 
+- Issue #25089: Adds logging to installer for case where launcher is not
+  selected on upgrade.
+
 - Issue #25165: Windows uninstallation should not remove launcher if other
   versions remain
 
diff --git a/Tools/msi/bundle/bootstrap/PythonBootstrapperApplication.cpp b/Tools/msi/bundle/bootstrap/PythonBootstrapperApplication.cpp
index 99884e4c9aa..bc418e0014f 100644
--- a/Tools/msi/bundle/bootstrap/PythonBootstrapperApplication.cpp
+++ b/Tools/msi/bundle/bootstrap/PythonBootstrapperApplication.cpp
@@ -687,6 +687,13 @@ public: // IBootstrapperApplication
             if (hr == S_FALSE) {
                 hr = LoadLauncherStateFromKey(_engine, HKEY_LOCAL_MACHINE);
             }
+            if (FAILED(hr)) {
+                BalLog(
+                    BOOTSTRAPPER_LOG_LEVEL_ERROR,
+                    "Failed to load launcher state: error code 0x%08X",
+                    hr
+                );
+            }
         } else if (BOOTSTRAPPER_RELATED_OPERATION_NONE == operation) {
             if (_command.action == BOOTSTRAPPER_ACTION_INSTALL) {
                 LOC_STRING *pLocString = nullptr;