Winter canola (Brassica napus) could be a good candidate for enhancing cropping systems in Iowa because of its potential to provide environmental benefits and produce a marketable crop compatible with existing grain production and distribution schemes. However, it is still uncertain whether this crop would be suitable for helping balance environmental and financial goals of conventional cropping systems under the environmental and market conditions unique to Iowa. The work presented in this thesis is an effort to assess the suitability of winter canola for providing environmental benefits while fitting within the logistic and economic constrains of current cropping systems. Based on observations from experimentation in field plots, it is determined that canola can be successfully established in the fall, survive the winter, and regrow in the spring, but adequate conditions during fall growth are crucial. It is estimated that seeding by 31 Aug in the north to 12 Sep in the southeast will allow enough time for adequate growth of canola during the fall in at least half of the years in Iowa. Because these seeding date requirements will likely conflict with standing crops during most years, adjustments to the rotation schemes of conventional rotations are needed. Therefore, two alternative systems are proposed, and their economic profiles are studied. Findings from this economic analysis suggest that these rotation alternatives produce relatively less net returns than the conventional corn (Zea mays L.)- soybean (Glycine max (L) Merr.) rotation, throughout a range of market and canola yield scenarios. Based on these results, it is determined that although winter canola can provide some environmental and economic enhancements to summer annual crop rotations in Iowa, but the specific situations in which canola can fit these rotations are limited. Nonetheless, more research is needed to fully understand the productivity potential of winter canola in Iowa, before counting these as feasible alternatives for producers in this state.