diff --git a/src/Dialogs.c b/src/Dialogs.c
index 647980d07..d4bb10ad2 100644
--- a/src/Dialogs.c
+++ b/src/Dialogs.c
@@ -4826,9 +4826,9 @@ void RestorePrevScreenPos(HWND hwnd)
 //
 //  DialogNewWindow()
 //
-void DialogNewWindow(HWND hwnd, bool bSaveOnRunTools, const HPATHL hFilePath, WININFO* wi)
+void DialogNewWindow(HWND hwnd, bool bSaveBeforeOpen, const HPATHL hFilePath, WININFO* wi)
 {
-    if (bSaveOnRunTools && !FileSave(FSF_Ask)) {
+    if (bSaveBeforeOpen && !FileSave(FSF_Ask)) {
         return;
     }
     WCHAR wch[80] = { L'\0' };
diff --git a/src/Dialogs.h b/src/Dialogs.h
index 233687c32..0ca8325c8 100644
--- a/src/Dialogs.h
+++ b/src/Dialogs.h
@@ -77,7 +77,7 @@ WINDOWPLACEMENT WindowPlacementFromInfo(HWND hwnd, const WININFO* pWinInfo, SCRE
 void            SnapToWinInfoPos(HWND hwnd, const WININFO winInfo, SCREEN_MODE mode, UINT nCmdShow);
 void            RestorePrevScreenPos(HWND hwnd);
 
-void DialogNewWindow(HWND hwnd, bool bSaveOnRunTools, const HPATHL hFilePath, WININFO* wi);
+void DialogNewWindow(HWND hwnd, bool bSaveBeforeOpen, const HPATHL hFilePath, WININFO* wi);
 void DialogFileBrowse(HWND hwnd);
 void DialogGrepWin(HWND hwnd, LPCWSTR searchPattern);
 void DialogAdminExe(HWND hwnd,bool);
diff --git a/src/Notepad3.c b/src/Notepad3.c
index c2a1ca9b6..906006545 100644
--- a/src/Notepad3.c
+++ b/src/Notepad3.c
@@ -3684,8 +3684,9 @@ static LRESULT _OnDropOneFile(HWND hwnd, HPATHL hFilePath, WININFO* wi)
     }
     else if (Path_IsExistingFile(hFilePath)) {
         //~ ignore Flags.bReuseWindow
+        bool const sameFile = (Path_StrgComparePath(hFilePath, Paths.CurrentFile, Paths.ModuleDirectory) == 0);
         if (IsKeyDown(VK_CONTROL) || wi) {
-            DialogNewWindow(hwnd, Settings.SaveBeforeRunningTools, hFilePath, wi);
+            DialogNewWindow(hwnd, sameFile, hFilePath, wi);
         } else {
             FileLoad(hFilePath, fLoadFlags, 0, 0);
         }
@@ -4840,7 +4841,7 @@ LRESULT MsgCommand(HWND hwnd, UINT umsg, WPARAM wParam, LPARAM lParam)
     case IDM_FILE_NEWWINDOW2: {
         SaveAllSettings(false);
         HPATHL hpth = (iLoWParam == IDM_FILE_NEWWINDOW2) ? Paths.CurrentFile : NULL;
-        DialogNewWindow(hwnd, Settings.SaveBeforeRunningTools, hpth, NULL);
+        DialogNewWindow(hwnd, (hpth != NULL), hpth, NULL);
     }
     break;
 
@@ -12117,7 +12118,7 @@ bool FileSave(FileSaveFlags fSaveFlags)
             LONG const answer = InfoBoxLng(typ, L"ReloadExSavedCfg", IDS_MUI_RELOADSETTINGS, tch);
             if (IsYesOkay(answer)) {
                 ///~SaveAllSettings(true); ~ already saved (CurrentFile)
-                DialogNewWindow(Globals.hwndMain, false, Paths.CurrentFile, NULL);
+                DialogNewWindow(Globals.hwndMain, true, Paths.CurrentFile, NULL);
                 CloseApplication();
             }
         }