A device implementing an adaptive wide area network (WAN) link assessment system may include a processor configured to transmit data to a WAN over a first link on a first wireless interface. The processor may be configured to, responsive to a determination based on connection information that a first escalation condition is satisfied, configure the first link to provide expanded connection information. The processor may be configured to, responsive to a second determination based on the expanded connection information that a second escalation condition is satisfied, perform a probe operation with respect to a server on the WAN over the first link. The processor may be further configured to, when the probe operation is not successfully completed within a predetermined amount of time, begin to transmit the data to the WAN over the second link on the second wireless interface.