We studied Ovenbird Seiurus aurocapilla and Golden-winged Warbler Vermivora chrysoptera populations in northern Minnesota, USA, to test two common assumptions in studies of songbird nest success: (1) that the condition of an empty nest on or near its expected fledge date is an indicator of nest fate; and (2) that the presence of a fledgling or family group within a territory confirms a successful nest in that territory. We monitored the condition of nests and used radiotelemetry to monitor juveniles through the expected fledging date and early post-fledging period. Of nests that contained nestlings 1–2 days before the expected fledge date, fates were misidentified using nest condition alone for 9.5% of Ovenbird nests, but those misidentifications were made in both directions (succeeded or failed), yielding only a small bias in estimated nest success. However, 20% of Golden-winged Warbler nests were misidentified as successful using nest condition during the final visit interval, biasing the nest success estimate upward by 21–28% depending on the treatment of uncertain nest fates. Fledgling Ovenbirds from 58% of nests travelled beyond their natal territory within 24 h, rising to 98% after 5 days, and those fledglings travelled up to 390 m from nests within 10 days of fledging. Fledgling Golden-winged Warblers from 13% of nests travelled beyond their natal territory within 24 h, rising to 85% after 5 days, and those fledglings travelled up to 510 m from nests within 10 days of fledging. We conclude that nest condition and fledgling presence can be misleading indicators of nest fate, probably commonly biasing nest success estimates upward, and we recommend that these assumptions should be tested in additional species.