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I'm working with a large number of labels that I've converted to annotation (using ArcMap 10.1). All of them need to fit within the parcel borders that they correspond to.

Is there a way to do it all at once or am I stuck going one by one to fit them in the boundaries?

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If you experiment with the Maplex Labelling Engine (part of Core at all license levels at 10.1) there is a chance that you may not need to create annotation.

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