Purpose of Review In this article, we consider advanced technologies for the management of diabetes. Recent Findings Specifically, we pose the question of which should come first: an insulin pump (CSII) or a continuous glucose monitor (CGM)? Historical perspective on both insulin delivery and glucose measurement is provided. Recently published clinical trials are reviewed. Practical issues including quality of life, patient education, and out-of-pocket cost are discussed. Summary Based on available evidence and clinical experience, we favor CGM as a first-line technology recommendation for the treatment of type 1 diabetes (T1D). Electronic supplementary material The online version of this article (10.1007/s11892-019-1177-7) contains supplementary material, which is available to authorized users.