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When you press Ctrl + F (Find, not Filter) in the Web GUI, a dialog like below appears:

Note here the checkbox for Case sensitive. What is the value? It seems to me it is case sensitive, or not. Not undecided. Once you've performed a search, the box is unchecked, which is assume it's default behavior.

In comparison, the Windows GUI doesn't have the box checked by default:

 

Is this a setting, intended or wrong? 

The web and windows GUI should have the same behavior. The checkbox has three states (undecided, checked and unchecked). The web gui has the undecided as the default state.  I agree that in this case this checkbox should have only 2 states, either checked or unchecked. I will create a bug for this.