Described herein are techniques for adding adaptive annotations to an electronic content item. For example, a user may insert an annotation by hand drawing the annotation over the content of the content item, in white space around the content, or within an annotation window. The user may also anchor, associate, or link annotations to particular portion of the content item, such that when the content is displayed or rendered on a display of an electronic device, the annotation appears in-line with the content and adjacent to the associated portion.