Little is known about restoring the perennial herbaceous understory of Midwestern deciduous woodlands, despite the significant and widespread degradation of remnants due to human activities. Because many woodland understory species have reproductive characters that make reestablishment from seed slow or difficult, we investigated transplanting as a strategy for introducing 24 species to a degraded early-successional woodland in central Iowa, U.S.A. Plants were planted in single-species groups of generally four individuals, and then monitored for survival five times over a 7-year period, and for flowering during the first year. After 7 years, persistence of these groups was 57% averaged across species. Survival in years 5–7 does not reflect individuals that spread beyond the original planting units by self-sowing or vegetative spread and is therefore a minimum estimate of the abundance of many species at the site. Mean percent flowering was 72% across single-species groups for 15 species monitored. We consider these survival and flowering rates acceptable indicators of establishment success, especially given drought conditions at our site in the first few years and lack of weed control beyond the first year, and evidence that transplanted species were establishing outside the original planting locations. Additional work is needed to investigate regional differences in transplant success, and methods for sustainable production of species are not suitable for introduction by seed. We caution that our results do not necessarily apply to the restoration of rare species.