While Six Sigma and other quality methodologies have been used extensively and quite effectively in the manufacturing sector for decades, the adoption rate in other industries such as the software development industry has been a bit slower. However, in recent years, research literature clearly suggests that the trend line is definitely on the upswing for software practitioners who see the value of applying Six Sigma and other proven quality methodologies in better managing software development projects, which have notoriously been prone to delays in migrating to production. We contemplate that the melding of these two methodologies will result in a sum that is greater than its two parts. In this paper, we elaborate on current issues/challenges of Six Sigma utilization in software development and management and explain problems that the software project managers encounter when dealing with them. We also investigate a broad collection of toolkits that are typically used in the Six Sigma framework and propose what tools, in each Six Sigma DMAIC (define, measure, analyze, improve, and control) phase are better candidates to consider and recuperate for software development and management.