Diminishing milkweed (Asclepias sp.) populations are contributing to the conspicuous decline of the iconic monarch butterfly (Danaus plexippus). This research sought to improve milkweed propagation success, a core component of summer habitat restoration projects. Specifically, this research assessed the effects of container volume and fertilizer application rate on growth and first year field survival of two species of milkweed common to western North America, namely showy milkweed (A. speciosa) and narrowleaf milkweed (A. fascicularis). Generally, larger roots and shoots developed when plants were given the high rate of fertilizer (6.5 g·L−1) and when reared in the largest containers (2600 mL). For narrowleaf milkweed, nearly all plants developed a firm plug (i.e., one in which the root system remained intact when removed from the container) after 22 weeks. Most narrowleaf milkweed plants flowered 15 weeks after sowing when grown in the largest container with either the low (2.7 g·L−1) or high fertilizer rate or the midsized container (444 mL) with a high rate of fertilizer. For showy milkweed, a firm plug developed for nearly all individuals by the end of the growing season only when given the high fertilizer rate. None of the showy milkweed plants developed an inflorescence by 15 weeks. Results of this research improve our understanding of milkweed propagation and will aid in the efforts to restore the monarch butterfly’s summer breeding habitat by providing propagation protocols across a range of stocktypes.