I'm using the following .NET 4.5.2 code:
if (this.ContainsFocus && keyData == (Keys.Tab|Keys.Shift))
{ ... }
Why is the expression true when ContainsFocus (bool = true) and keyData (System.Windows.Forms.Keys) is Keys.O | Keys.Shift?
As you can see the breakpoint is hit:

with this values:

A workaround for this bug (?!) is:
if (this.ContainsFocus && (int)keyData == (int)(Keys.Tab|Keys.Shift))
{ ... }
No, HasFlag does not have a bug. Unfortunately, the .NET FlagsAttribute is all or nothing and System.Windows.Forms.Keys is defined in such a way that only Keys.Modifiers may be used as flags.
From https://msdn.microsoft.com/en-us/library/system.windows.forms.keys%28v=vs.110%29.aspx
The Keys class contains constants for processing keyboard input. The members of the Keys enumeration consist of a key code and a set of modifiers combined into a single integer value. In the Win32 application programming interface (API) a key value has two halves, with the high-order bits containing the key code (which is the same as a Windows virtual key code), and the low-order bits representing key modifiers such as the SHIFT, CONTROL, and ALT keys.
As a result, you can check any of the modifiers (Keys.Shift, Keys.Alt, Keys.Control) with HasFlag, but nothing else.
This is not a bug of HasFlag, it is how it work.
Suppose we have the following values:
var a = (Keys.Tab | Keys.Shift);
var b = (Keys.O | Keys.Shift);
Now we analyze the bits of these values (when we cast them to integers):
a: 10000000001000001
b: 10000000001001111
If we call a.HasFlag(b) we get false because not every 1-bit from b is a 1 in a too. But if we call b.HasFlag(a) we get true because every 1-bit of a is set in b too.
That's why you need to compare the values with a==b or with a.HasFlag(b) && b.HasFlag(a). Then it will work properly.
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