diff --git a/src/osx/carbon/frame.cpp b/src/osx/carbon/frame.cpp
index d0033a3d5d..5d6a0bd47d 100644
--- a/src/osx/carbon/frame.cpp
+++ b/src/osx/carbon/frame.cpp
@@ -62,11 +62,11 @@ wxPoint wxFrame::GetClientAreaOrigin() const
         int w, h;
         toolbar->GetSize(&w, &h);
 
-        if ( toolbar->HasFlag(wxTB_LEFT) )
+        if ( toolbar->HasFlag(wxTB_LEFT) && !toolbar->HasFlag(wxTB_RIGHT) )
         {
             pt.x += w;
         }
-        else if ( toolbar->HasFlag(wxTB_TOP) )
+        else if ( toolbar->HasFlag(wxTB_TOP) && !toolbar->HasFlag(wxTB_BOTTOM) )
         {
 #if !wxOSX_USE_NATIVE_TOOLBAR
             pt.y += h;
@@ -342,14 +342,12 @@ void wxFrame::PositionToolBar()
 
         tx = ty = 0 ;
         GetToolBar()->GetSize(&tw, &th);
-        if (GetToolBar()->HasFlag(wxTB_LEFT))
-        {
-            // Use the 'real' position. wxSIZE_NO_ADJUSTMENTS
-            // means, pretend we don't have toolbar/status bar, so we
-            // have the original client size.
-            GetToolBar()->SetSize(tx , ty , tw, ch , wxSIZE_NO_ADJUSTMENTS );
-        }
-        else if (GetToolBar()->HasFlag(wxTB_RIGHT))
+
+        // Note: we need to test for wxTB_RIGHT before wxTB_LEFT, as the latter
+        // is the same as wxTB_VERTICAL and it's possible to combine wxTB_RIGHT
+        // with wxTB_VERTICAL, so testing for wxTB_LEFT could be true for a
+        // right-aligned toolbar (while the reverse is, luckily, impossible).
+        if (GetToolBar()->HasFlag(wxTB_RIGHT))
         {
             // Use the 'real' position. wxSIZE_NO_ADJUSTMENTS
             // means, pretend we don't have toolbar/status bar, so we
@@ -357,6 +355,13 @@ void wxFrame::PositionToolBar()
             tx = cw - tw;
             GetToolBar()->SetSize(tx , ty , tw, ch , wxSIZE_NO_ADJUSTMENTS );
         }
+        else if (GetToolBar()->HasFlag(wxTB_LEFT))
+        {
+            // Use the 'real' position. wxSIZE_NO_ADJUSTMENTS
+            // means, pretend we don't have toolbar/status bar, so we
+            // have the original client size.
+            GetToolBar()->SetSize(tx , ty , tw, ch , wxSIZE_NO_ADJUSTMENTS );
+        }
         else if (GetToolBar()->HasFlag(wxTB_BOTTOM))
         {
             tx = 0;
diff --git a/src/osx/cocoa/toolbar.mm b/src/osx/cocoa/toolbar.mm
index a0bb728b03..89bbbf200e 100644
--- a/src/osx/cocoa/toolbar.mm
+++ b/src/osx/cocoa/toolbar.mm
@@ -1688,10 +1688,14 @@ void wxToolBar::OnPaint(wxPaintEvent& event)
         }
         
         dc.SetPen( wxPen( wxColour( 0x51,0x51,0x51 ) ) );
-        if ( HasFlag(wxTB_LEFT) )
-            dc.DrawLine(w-1, 0, w-1, h);
-        else if ( HasFlag(wxTB_RIGHT) )
+
+        // Note that testing this is in the "reverse" order, i.e. right before
+        // left and bottom before top because these flags can actually be
+        // combined because left/top are the same as vertical/horizontal
+        if ( HasFlag(wxTB_RIGHT) )
             dc.DrawLine(0, 0, 0, h);
+        else if ( HasFlag(wxTB_LEFT) )
+            dc.DrawLine(w-1, 0, w-1, h);
         else if ( HasFlag(wxTB_BOTTOM) )
             dc.DrawLine(0, 0, w, 0);
         else if ( HasFlag(wxTB_TOP) )