diff --git a/imgui.cpp b/imgui.cpp
index 43409848e..5efb3a6e2 100644
--- a/imgui.cpp
+++ b/imgui.cpp
@@ -15904,9 +15904,10 @@ static void WindowSettingsHandler_Cleanup(ImGuiContext* ctx, ImGuiSettingsHandle
     ImGuiContext& g = *ctx;
     for (ImGuiWindowSettings* settings = g.SettingsWindows.begin(); settings != NULL; settings = g.SettingsWindows.next_chunk(settings))
     {
-        if (args->_DiscardOlderThanDate != 0 && settings->LastUsedDate.Unpack() < args->_DiscardOlderThanDate)
+        const bool is_valid = settings->LastUsedDate.IsValid();
+        if ((args->_DiscardOlderThanDate != 0 && settings->LastUsedDate.Unpack() < args->_DiscardOlderThanDate) || (args->DiscardWhenMissingDate && !is_valid))
             settings->WantDelete = true;
-        if (args->SetCurrentSessionDateToAll || (args->SetCurrentSessionDateWhenMissingDate && settings->LastUsedDate.IsValid() == false))
+        if (args->SetCurrentSessionDateToAll || (args->SetCurrentSessionDateWhenMissingDate && !is_valid))
             settings->LastUsedDate = g.SessionDate;
     }
 }