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I am trying to add one type of effect to each shape in a group/layer. But when I set the appearance panel accordingly, either nothing happens, or (in the case of dropshadow) the shapes extend beyond their outlines to where the shadows would be rendered (See the picture).

I have tried doing this in multiple documents and it always happens, when trying to apply an effect to the appearance of a group/layerThis is what happens when applying a dropshadow (Schlagschatten) to a groups (Gruppe) appearance (Aussehen)

How can I fix this?

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The issue is where the dropshadow is in your appearance panel. As it appears above the content it is computing the dropshadow and then the content after that that (the fill colour).

Try changing your layers to

Group
 - Contents
 - Drop Shadow
 - Opacity
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Are you trying to apply the effect to the entire group, or each individual shape within the group/layer? For drop shadow (as is on your screen), if the objects are grouped, the effect will be applied to the outline of the entire group. You must isolate each individual object within the group, or apply the drop shadow effect to the selected objects before grouping them, to affect them individually.

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