Consider a font family with a weight=300 member and a weight = 600 member. Consider the following content:
<div id="outer" style="font: 300 16px MyFontFamily;">
<div id="inner" style="font-weight: bolder;">...</div>
</div>
The definition of bolder says that the computed weight for inner would be 400. According to the font matching rules, if the requested weight is 400, a candidate font of weight 300 would be chosen rather than another candidate of weight 600.
This means that, for the inner element, the author has requested a bolder weight, but they didn't get one, even though a bolder weight exists.
Maybe bolder should take into account which members of the family are present, so this situation would match the weight=600 font rather than the weight=300 font.