An enhanced bypass mode simulcast radio communication system (200) includes a plurality of transmit/receive (T/R) sites (2101, 2102, 2103) configured to participate in a simulcasting communication session responsive to a control point system (201). A site controller (211) is responsive to determination of a timing malfunction at a first one of the T/R sites. In response, the site controller is configured to automatically terminate participation of the malfunctioning T/R site in the simulcasting communication session and perform further actions to cause the malfunctioning site to transition to a multisite mode of operation involving a network switching center (202). The simulcast system automatically adjusts its site timing to compensate for the loss of the T/R site in bypass.