Seedling size is a very important issue when producing plants for restoration projects. Scientific evidence on the appropriate size for drylands is contradictory. Thus, the aim of this study was to evaluate the effect of seedling size during first establishment by conducting a short term greenhouse experiment with Pinus canariensis containerized seedlings. A selection of large (mean height: 33.7 cm) and small (14.3 cm) one-year-old seedlings were planted in pots under two volumetric water content regimes: dry (7%) and wet (15%). Midday shoot water potential was measured in two periods: 10 (prior to root protrusion) and 30 (once the roots had protruded from the plug) days after planting. The length of protruding roots was measured after 30 days. One month after planting, the large seedlings under the dry regime produced more new roots than the small seedlings, but also showed the highest midday water potential values. Therefore, the greater root growth of the former did not offset the higher transpiration demand when planted in dry soils. These results suggest that under uncertainty about the soil humidity levels of dry areas, using small seedlings can improve their short-term survival after planting.