diff --git a/docs/changes.txt b/docs/changes.txt
index 2d07d90137..0d4964a3c6 100644
--- a/docs/changes.txt
+++ b/docs/changes.txt
@@ -264,6 +264,7 @@ wxMSW:
 - Fix return value of wxZoomGestureEvent::GetZoomFactor() (s-murphree, #22818).
 - Update top level icon resolution on DPI change (#22807).
 - Remove "Printing" from title when printing to PDF (Blake-Madden, #22836).
+- Fix sometimes missing overvwrite prompt in "Save" file dialog (#22898).
 
 wxOSX:
 
diff --git a/src/msw/filedlg.cpp b/src/msw/filedlg.cpp
index a298bdaaab..89104ce539 100644
--- a/src/msw/filedlg.cpp
+++ b/src/msw/filedlg.cpp
@@ -1597,6 +1597,16 @@ int wxFileDialog::ShowIFileDialog(WXHWND hWndParent)
         hr = fileDialog->SetFileTypeIndex(m_filterIndex + 1);
         if ( FAILED(hr) )
             wxLogApiError(wxS("IFileDialog::SetFileTypeIndex"), hr);
+
+        // We need to call SetDefaultExtension() to make the file dialog append
+        // the selected extension by default. It will append the correct
+        // extension depending on the current file type choice if we call this
+        // function, but won't do anything at all without it, so find the first
+        // extension associated with the selected filter and use it here.
+        wxString defExt =
+            wildFilters[m_filterIndex].BeforeFirst(';').AfterFirst('.');
+        if ( !defExt.empty() && defExt != wxS("*") )
+            fileDialog->SetDefaultExtension(defExt.wc_str());
     }
 
     if ( !m_dir.empty() )
@@ -1608,7 +1618,7 @@ int wxFileDialog::ShowIFileDialog(WXHWND hWndParent)
     {
         hr = fileDialog->SetFileName(m_fileName.wc_str());
         if ( FAILED(hr) )
-            wxLogApiError(wxS("IFileDialog::SetDefaultExtension"), hr);
+            wxLogApiError(wxS("IFileDialog::SetFileName"), hr);
     }