Tooltips Not Shown Above Taskbar / Taskbar Popup

[nonsensesoftware]

If you try to show the tooltip, either via ToolTipText or TrayToolTIp, the tooltip can get into a state where it does not show above the Windows Taskbar. This only occurs when the Windows Start Menu is also open at the same time. See included image.

Is there a workaround to get this to show properly? Other applications don't seem to have an issue showing their tooltips. This can be reproduced by running any of the sample applications and hovering over the icon when the start menu is open.