Ensuring an adequate food supply and enough energy to sustainably support future global populations will require enhanced productivity from plants. Oilseeds can help address these needs; but the fatty acid composition of seed oils is not always optimal, and higher yields are required to meet growing demands. Quantitative approaches including metabolic flux analysis can provide insights on unexpected metabolism (i.e., when metabolism is different than in a textbook) and can be used to guide engineering efforts; however, as metabolism is context-specific, it changes with tissue type, local environment, and development. This review describes recent insights from metabolic flux analysis in oilseeds and indicates engineering opportunities based on emerging topics and developing technologies that will aid quantitative understanding of metabolism and enable efforts to produce more oil. We also suggest that investigating the key regulators of fatty acid biosynthesis, such as transcription factors, and exploring metabolic signals like phytohormones in greater depth through flux analysis, could open new pathways for advancing genetic engineering and breeding strategies to enhance oil crop production.