I'm experiencing some strange behavior. Let me try to explain, I stripped my code down to the bare minimum and I'm still having the problem. So first of all, I'm using VS2013 with .NET 4.0 and I'm on Windows 8.1.
So I have a custom UserControl with a TextBox that's being used through a ToolStripControlHost, if I focus on this textbox and hit TAB, it only cycles through the controls to the LEFT of this textbox.  If I have it focused and hit SHIFT+TAB, it cycles through the buttons to the right of it.

So this is an example of my form. The textbox in the middle is a custom control. My code (as simplified as possible) looks like:
[ToolStripItemDesignerAvailability(ToolStripItemDesignerAvailability.ToolStrip | ToolStripItemDesignerAvailability.StatusStrip)]
public class ToolStripTestControl : ToolStripControlHost
{
    public ToolStripTestControl() : this(new TestControl()) { }
    public ToolStripTestControl(Control c) : base(c) { }
}
public class TestControl : UserControl
{
    private TextBox _textBox = new TextBox();
    public TestControl()
    {
        _textBox.Dock = DockStyle.Fill;
        this.Controls.Add(_textBox);
    }
    protected override Size DefaultMinimumSize { get { return new Size(100, 22); } }
}
Simply creating a new WinForms (.NET4) project and following these steps will allow you to replicate the problem:
- Add new class file and paste the code above.
 - Build
 - Add a ToolStrip to your form
 - On the ToolStrip add a Button, my custom control, and another Button (through the designer is how I've been doing it)
 - Run
 
Once running...
- Focus in the custom control
 - Hit TAB a few times, it should only focus on controls to the left.
 - Hit SHIFT+TAB a few times and it will only focus to the right.
 
Does anyone know what the problem is - or how I can fix this?  I've been tearing my hair out all day trying to fix this.  I finally stripped my code down and I can't seem to get it to work.  I even tried overriding much of the OnEnter/OnGotFocus functionality and doing it myself, but that became a nightmare.
Thanks!
Update1: So a few extra tid-bits.
If I change the custom control to inherit from TextBox instead of UserControl, tabbing/focus works as expected.
If I change it to be a Control instead of a UserControl the tabbing works fine, as well, however the focus never gets inside my inner TextBox - the focus seems to be lost (or presumably on the outer parent control but not being passed down to the inner TextBox).
I do see a MS Connect item added that describes this problem from 2009, but this link only seems to work if I'm NOT logged in to Microsoft Connect. Which means, I can't vote on it or comment... http://connect.microsoft.com/VisualStudio/feedback/details/472592/tab-cycling-through-controls-with-usercontrol-on-toolstrip-doesnt-perform-as-expected