As online educational programs and courses increase (Allen & Seaman, [Allen, I. E., 2014]), it is important to understand the benefits and limitations of this delivery format when assessing students and when comparing learning outcomes. This article addresses the following two questions: (1) What are some of the best practices in assessing language skills online and how do they differ from assessment in face-to-face (F2F) courses? (2) How do learning outcomes differ in online vs. F2F courses? Both questions are answered based on previous research and our own practices and results in second-year German. We found that the most effective online practices are too time-consuming and costly to implement. Poor computer literacy skills and test security can be further issues in online environments. The solution lies in frequent formal and informal assessments. When comparing online with F2F language learning, meta-analyses give online formats a slight advantage over F2F (Means, Toyama, Murphy, Bakia, & Jones, [Means, B., 2009]). In this study no significant differences were found between the F2F and online sections. Noteworthy, however, is that large differences in standard deviations and score ranges between online and F2F classes suggest that online language learning works well for some and not as well for others.