diff --git a/src/msw/textctrl.cpp b/src/msw/textctrl.cpp
index 985664755c..16bb3cceff 100644
--- a/src/msw/textctrl.cpp
+++ b/src/msw/textctrl.cpp
@@ -65,7 +65,21 @@
 #if wxUSE_RICHEDIT
     #include <richedit.h>
     #include <richole.h>
+
+    // MinGW32 doesn't have tom.h and doesn't define the interfaces and the
+    // constants we need, so we can't use ITextDocument::Undo() with it. All
+    // the other compilers do have this header.
+    #ifndef __MINGW32_TOOLCHAIN__
+        #define wxHAS_TOM_H
+    #endif
+
+    #ifdef wxHAS_TOM_H
+        #include <tom.h>
+    #endif
+
     #include "wx/msw/ole/oleutils.h"
+
+    #include "wx/msw/private/comptr.h"
 #endif // wxUSE_RICHEDIT
 
 #if wxUSE_INKEDIT
@@ -129,6 +143,17 @@ DEFINE_GUID(wxIID_IRichEditOleCallback,
     0x00020d03, 0x0000, 0x0000, 0xc0, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x46);
 
 } // anonymous namespace
+
+#ifdef wxHAS_TOM_H
+
+// This one is not defined in the standard libraries at all and MSDN just says
+// to define it explicitly, so we do it for IID_XXX constant itself and not our
+// own wxIID_XXX.
+DEFINE_GUID(IID_ITextDocument,
+    0x8cc497c0, 0xa1df, 0x11ce, 0x80, 0x98, 0x00, 0xaa, 0x00, 0x47, 0xbe, 0x5d);
+
+#endif // wxHAS_TOM_H
+
 #endif // wxUSE_OLE
 
 // ----------------------------------------------------------------------------
@@ -668,6 +693,34 @@ bool wxTextCtrl::MSWCreateText(const wxString& value,
         ::SendMessage(GetHwnd(), EM_SETMARGINS, wParam, lParam);
     }
 
+#if wxUSE_RICHEDIT && defined(wxHAS_TOM_H)
+    // For RichEdit >= 4, SetFont(), called above from MSWCreateControl(), uses
+    // EM_SETCHARFORMAT which affects the undo buffer, meaning that CanUndo()
+    // for a newly created control returns true, which is unexpected. To avoid
+    // this, we explicitly use Undo(tomFalse) here to clear the undo buffer.
+    // And since Undo(tomFalse) also disables the undo buffer, we need to
+    // enable it again immediately after clearing by calling Undo(tomTrue).
+    if ( GetRichVersion() >= 4 )
+    {
+        wxCOMPtr<IRichEditOle> pRichEditOle;
+        if ( SendMessage(GetHwnd(), EM_GETOLEINTERFACE,
+                         0, (LPARAM)&pRichEditOle) && pRichEditOle )
+        {
+            wxCOMPtr<ITextDocument> pDoc;
+            HRESULT hr = pRichEditOle->QueryInterface
+                                       (
+                                        wxIID_PPV_ARGS(ITextDocument, &pDoc)
+                                       );
+            if ( SUCCEEDED(hr) )
+            {
+                hr = pDoc->Undo(tomFalse, NULL);
+                if ( SUCCEEDED(hr) )
+                    pDoc->Undo(tomTrue, NULL);
+            }
+        }
+    }
+#endif // wxUSE_RICHEDIT && wxHAS_TOM_H
+
     return true;
 }
 
diff --git a/tests/controls/textctrltest.cpp b/tests/controls/textctrltest.cpp
index e07c218d67..d30c620d0a 100644
--- a/tests/controls/textctrltest.cpp
+++ b/tests/controls/textctrltest.cpp
@@ -1432,4 +1432,35 @@ TEST_CASE("wxTextCtrl::EventsOnCreate", "[wxTextCtrl][event]")
     CHECK( updated.GetCount() == 1 );
 }
 
+TEST_CASE("wxTextCtrl::InitialCanUndo", "[wxTextCtrl][undo]")
+{
+    wxWindow* const parent = wxTheApp->GetTopWindow();
+
+    const long styles[] = { 0, wxTE_RICH, wxTE_RICH2 };
+
+    for ( size_t n = 0; n < WXSIZEOF(styles); n++ )
+    {
+        const long style = styles[n];
+
+#ifdef __MINGW32_TOOLCHAIN__
+        if ( style == wxTE_RICH2 )
+        {
+            // We can't call ITextDocument::Undo() in wxMSW code when using
+            // MinGW32, so this test would always fail with it.
+            WARN("Skipping test known to fail with MinGW-32.");
+        }
+        continue;
+#endif // __MINGW32_TOOLCHAIN__
+
+        INFO("wxTextCtrl with style " << style);
+
+        wxScopedPtr<wxTextCtrl> text(new wxTextCtrl(parent, wxID_ANY, "",
+                                                    wxDefaultPosition,
+                                                    wxDefaultSize,
+                                                    style));
+
+        CHECK( !text->CanUndo() );
+    }
+}
+
 #endif //wxUSE_TEXTCTRL