Numerical simulations of turbulence provide non-intrusive access to all the resolved scales and any quantity of interest, although they often invoke idealizations and assumptions that can compromise realism. In contrast, experimental measurements probe the true flow with lesser idealizations, but they continually contend with spatio-temporal sensor resolution. Assimilating observations directly in simulations can combine the benefits of both approaches and mitigate their respective deficiencies. The problem is expressed in variational form, where we seek the flow field that satisfies the Navier-Stokes equations and minimizes a cost function defined in terms of the deviation of the computational predictions and available observations. In this framework, measurements are no longer a mere record of the instantaneous, local quantity, but rather an encoding of the antecedent flow events that we aim to decode using the governing equations. Chaos plays a central role in obfuscating the interpretation of the data: observations that are infinitesimally close may be due to entirely different earlier conditions. We examine a number of state estimation problems: In circular Couette flow, starting from observations of the wall stress, we accurately reconstruct the wavy Taylor vortices that interact nonlinear to maintain a saturated state. Through a discussion of transition to chaos in a Lorenz system, we highlight the challenge of navigating the landscape of the cost function, and how the landscape can favorably be modified by sensor weighting and placement. In turbulent channel flow, the Taylor microscale and Lyapunov timescale place restrictions on the resolution of observations for which we can accurately reconstruct all the missing scales. The notion of domain of dependence of an observation is introduced and related to the Hessian of the cost function. For measurements of wall shear stress, the eigenspectrum of the Hessian demonstrates the sensitivity of short-time observations to the fine near-wall turbulent scales and to the large scales only in the outer flow. At long times, backward chaos obfuscates the interpretation of the data: observations that are infinitesimally close may be traced back to entirely different earlier flow states-a dual to the more common butterfly effect for forward trajectories.