We study the problem of optimally sending a real-valued source through multiple uses of a channel with feedback. First, we state a set of conditions that are sufficient for an encoder to achieve maximal mutual information between the source and all the channel outputs. This set of conditions are also necessary when the channel is input-identifiable, a condition widely satisfied by common channel models. More notably, we further study the information maximization-distortion minimization problem, where the mutual information between the source and all channel outputs still needs to be maximized, while at each step, the MMSE of estimating the source from the channel outputs so far also needs to be minimized. We derive a solution to this problem for discrete channels with certain symmetries, e.g. $k$-ary symmetric or $k$-ary erasure channels. We show that for such channels the famous posterior matching scheme, while not necessary for information maximization alone, is sufficient and essentially necessary for achieving both information maximization and distortion minimization. This work also provides a new perspective of regularizing distortion-minimizing feedback communication through information maximization, which enables us to find the optimal solution that otherwise would be intractable.