A method for integrated retrieval and annotation of stored images involves running a user application in which text entered by a user is continuously monitored to isolate the context expressed by the text. The context is matched with metadata associated with the stored images, thereby providing one or more matched images, and the matched images are retrieved and displayed in proximity with the text. The context is then utilized to provide suggested annotations to the user for the matched images, together with the capability of selecting certain of the suggested annotations for subsequent association with the matched images. In a further extension, the method provides the user with the capability of inserting selected ones of the matched images into the text of the application, and further provides for automatically updating the metadata for the matched images.