Watering up typically ensues after clearcutting forestry-drained peatland forests. Thus, the effectiveness of maintenance drainage and soil preparation procedures becomes paramount for establishing a new generation of commercial forest. Mounding is the primary method of soil preparation applied in regeneration sites lying on deep peat. As raised planting spots, mounds are resistant to waterlogging and assumed to be beneficial for organic matter (OM) decomposition via, e.g., increased soil aeration and temperature, which would also enhance seedling growth. In recent years, however, less intensive and cheaper alternatives like scalping have been sought with some reported cases of success. Our case study investigated the survival and growth of Scots pine outplants in mounds, scalps, and unprepared microsites along a moisture gradient. After three growing seasons, mounding accelerated neither seedling growth nor OM decomposition relative to the unprepared treatment. Survival in mounds was nonetheless superior overall. Scalps behaved as water collecting depressions leading to a catastrophic regeneration result. Based on our findings, water table level (WTL) overrides other growth-controlling factors in excess moisture conditions. To combat watering up coupled with greater than normal rainfall, we recommend reforestation strategies which provide elevated, prepared planting spots (i.e., mounds) or utilize unprepared, higher microforms.