The Achilles tendon (AT) is a complex structure, consisting of distinct fascicle bundles arising from each triceps surae muscle that may act as mechanically independent structures. Advances in tissue imaging are rapidly accelerating our understanding of the complexities of functional Achilles tendon behavior, with potentially important implications for musculoskeletal injury and performance. In this overview of our recent contributions to these efforts, we present the results of complementary experimental and computational approaches to investigate AT behavior during walking and its potential relevance to reduced triceps surae mechanical performance due to aging. Our experimental evidence reveals that older tendons exhibit smaller differences in tissue deformations than young adults between regions of the AT presumed to arise from the gastrocnemius and soleus muscles. These observations are consistent with a reduced capacity for inter-fascicle sliding within the AT, which could have implications for the mechanical independence of the triceps surae muscles. More uniform AT deformations are also correlated with hallmark biomechanical features of elderly gait – namely, a loss of net ankle moment, power, and positive work during push-off. Simulating age-related reductions in the capacity for inter-fascicle sliding in the AT during walking predicts detriments in gastrocnemius muscle-tendon mechanical performance coupled with underlying shifts in fascicle kinematics during push-off. AT compliance, also suspected to vary due to age, systematically modulates those effects. By integrating in vivo imaging with computational modeling, we have gained theoretical insight into multi-scale biomechanical changes due to aging, hypotheses regarding their functional effects, and opportunities for experiments that validate or invalidate these assertions.