Challah, Kugal and Cookies
Halacha Orach Chaim 168
Someone wants to eat cookies in the middle of a meal. There is a discussion if a Bracha is needed.
According to the Chofetz Chaim in Biyur Halacha opposite page 134, one should almost never recite a Bracha when eating cookies or other items we call Pas Haba Bekisnin in the middle of a meal.
The reason for this is as follows. We mentioned earlier that there are three opininos what Pas Habah Bekisnin is. Accordingly, when someone is snacking on a food that may qualify as Pas Haba Bekisnin, we consider the food in question a Mezonos, because we always rule lenient when it comes to questions on Brachos.
However, when it comes to eating cookies, or other Pas Habah Bekisnin during a meal, we consider the cookies a Hamotzei food. This is because a bread food will not require a Bracha, as a Hamotzei was already recited, and a snack food will require a Bracha, since Mezonos was not recited.
In summary, a Mezonos is recited on cookies instead of Hamotzei when eaten as a snack, but a Bracha is not recited on cookies when eaten during a meal, as we consider it like bread. This is because we always rule leniently, even though these two rules seem contradictory.
The same Halacha should apply by dessert as well, and a Mezonos should not be recited. However, if the Mezonos is a mixture of all three types of Pas Habah Bekisnin, like some jelly cookies, or pie, a Bracha should obviously be said.

