Draw Inside and Draw Behind are modes that are in Illustrator CS5 only. They are available on the bottom of your Tools Panel.

Draw Normal mode

This is the way Illustrator has always drawn graphics (see image below):

Draw Behind mode

Draw below a selected object.
NOTE: unless you check the icons in the Tools Panelyou may not be aware that you’re in this mode (see image below):

Draw Inside mode

Draw inside a selected object (see image below):

Cycle through these modes using Shift-D (⇧D).

Double-click anywhere outside your artwork to return to Draw Normal mode.

Drawing Behind

First, select the object that you wish to Draw Behind (see image below):

Then start drawing your object (see image below):

Your finished drawing will be covered by your selected object (see image below):

Drawing Inside

First, select the object that you wish to Draw Inside – notice the dotted lines indicating your selection as a Draw Inside selection (see image below):

Then start drawing on your object (see images below):

Your finished drawing will be inside your selected object (see image below):

NOTE: You do not have to start your inside drawing within the boundaries of your selected object. Below is the Line Tool being used to draw inside an object (see images below):

NOTE: Anything you've drawn behind or inside can be moved to the top (see images below):

Any questions?

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