diff --git a/src/dialog/windows/SDL_windowsdialog.c b/src/dialog/windows/SDL_windowsdialog.c
index 631fff5c18..400fcf03ad 100644
--- a/src/dialog/windows/SDL_windowsdialog.c
+++ b/src/dialog/windows/SDL_windowsdialog.c
@@ -456,6 +456,9 @@ char *clear_filt_names(const char *filt)
     return cleared;
 }
 
+// This function returns NOT success or error, but rather whether the callback
+// was invoked or not (and if it was, no fallback should be attempted to prevent
+// calling the callback twice). See https://github.com/libsdl-org/SDL/issues/15194
 bool windows_ShowModernFileFolderDialog(SDL_FileDialogType dialog_type, const char *default_file, SDL_Window *parent, bool allow_many, SDL_DialogFileCallback callback, void *userdata, const char *title, const char *accept, const char *cancel, wchar_t *filter_wchar, int nfilters)
 {
     bool is_save = dialog_type == SDL_FILEDIALOG_SAVEFILE;
@@ -488,7 +491,8 @@ bool windows_ShowModernFileFolderDialog(SDL_FileDialogType dialog_type, const ch
     wchar_t *default_file_w = NULL;
     wchar_t *default_folder_w = NULL;
 
-    bool success = false;
+    bool callback_called = false;
+    bool call_callback_on_error = false;
     bool co_init = false;
 
     // We can assume shell32 is already loaded here.
@@ -604,6 +608,10 @@ bool windows_ShowModernFileFolderDialog(SDL_FileDialogType dialog_type, const ch
         CHECK(pFileDialog->lpVtbl->SetFileName(pFileDialog, default_file_w));
     }
 
+    // Right after this, a dialog is shown. No fallback should be attempted on
+    // error to prevent showing two dialogs to the user.
+    call_callback_on_error = true;
+
     if (parent) {
         HWND window = (HWND) SDL_GetPointerProperty(SDL_GetWindowProperties(parent), SDL_PROP_WINDOW_WIN32_HWND_POINTER, NULL);
 
@@ -616,7 +624,7 @@ bool windows_ShowModernFileFolderDialog(SDL_FileDialogType dialog_type, const ch
             // This is a one-based index, not zero-based. Doc link in similar comment below
             CHECK(pFileDialog->lpVtbl->GetFileTypeIndex(pFileDialog, &selected_filter));
             callback(userdata, results, selected_filter - 1);
-            success = true;
+            callback_called = true;
             goto quit;
         } else if (!SUCCEEDED(hr)) {
             goto quit;
@@ -631,7 +639,7 @@ bool windows_ShowModernFileFolderDialog(SDL_FileDialogType dialog_type, const ch
             // This is a one-based index, not zero-based. Doc link in similar comment below
             CHECK(pFileDialog->lpVtbl->GetFileTypeIndex(pFileDialog, &selected_filter));
             callback(userdata, results, selected_filter - 1);
-            success = true;
+            callback_called = true;
             goto quit;
         } else if (!SUCCEEDED(hr)) {
             goto quit;
@@ -665,7 +673,7 @@ bool windows_ShowModernFileFolderDialog(SDL_FileDialogType dialog_type, const ch
         }
 
         callback(userdata, (const char * const *) files, selected_filter - 1);
-        success = true;
+        callback_called = true;
     } else {
         // This is a one-based index, not zero-based.
         // https://learn.microsoft.com/en-us/windows/win32/api/shobjidl_core/nf-shobjidl_core-ifiledialog-getfiletypeindex#parameters
@@ -681,18 +689,17 @@ bool windows_ShowModernFileFolderDialog(SDL_FileDialogType dialog_type, const ch
         }
         const char * const results[] = { file, NULL };
         callback(userdata, results, selected_filter - 1);
-        success = true;
+        callback_called = true;
         SDL_free(file);
     }
 
-    success = true;
-
 #undef CHECK
 
 quit:
-    if (!success) {
-        WIN_SetError("dialogg");
+    if (!callback_called && call_callback_on_error) {
+        WIN_SetError("dialog");
         callback(userdata, NULL, -1);
+        callback_called = true;
     }
 
     if (co_init) {
@@ -750,7 +757,7 @@ quit:
         SDL_free(files);
     }
 
-    return success;
+    return callback_called;
 }
 
 // TODO: The new version of file dialogs