Abstract: An improved automated media scheduling system includes a conditional scheduler operating in cooperation with the at least one master scheduler to obtain a contextual condition associated with a conditional media item, and devoid of entity identification information. Satisfying the contextual condition is a prerequisite to pairing the conditional media item with another media item. The conditional scheduler obtains an original schedule generated by the master scheduler, identifies a scheduled media item, from the original schedule, that satisfies the contextual condition, pairs the conditional media item and the scheduled media item to generate a media item pair, and transmits a proposed scheduling change, including the media item pair, to the master scheduler. The master scheduler evaluates the proposed scheduling change for compliance with scheduling rules.

Abstract: Advertisements can be paired based on their context to achieve increased advertising effectiveness that might not be able to be achieved without the pairing. The advertisements can be paired based on a user's preferred context, which includes an attribute of one of the advertisements. For example, a conditional advertisement can be paired with a scheduled advertisement based on an industry type, the length of the other advertisement, or some other characteristic. Each characteristic can be given a weight, to aid in pairing determinations. The effectiveness of the pairing can be tracked, and the context can be iteratively modified based on the measured effectiveness of the advertising campaign. Pairing can be performed without identifying other advertisers, even though weighting factors may take a sponsor's identity into account. Pairing can be constrained by a master schedule and by a maximum allowed number of conditional spots.