I had a similar problem today. Sometimes, the tooltip would not show. I had one ToolTip control for all the controls in my form.
I also had a MouseEnter event on all the controls added automatically, so I modified the MouseEnter event to do:
_tooltip.Active = false;
_tooltip.Active = true;
It fixed the bug, but I don't know why.
Also, the bug always happened on Windows XP machines, but not on Windows Vista.
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