Future data connection quality may be predicted based on past data connection quality, and future requests for data may be predicted based on past requests. These predictions may be used to help decide whether, when, and/or how to deliver the data in a proactive manner. For example, according to some aspects described herein, a future data connection quality may be predicted based at least on historical data connection quality. It may be determined whether to pre-deliver at least a first portion of an item of content based at least on the predicted future data connection quality. If so, then the at least the portion of the item of content may be pre-delivered to the device and/or to another destination.