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In this paper, we study a sampling problem where a source takes samples from a Wiener process and transmits them through a wireless channel to a remote estimator. Due to channel fading, interference, and potential collisions, the packet transmissions are unreliable and could take random time durations. Our objective is to devise an optimal causal sampling policy that minimizes the long-term average mean square estimation error. This optimal sampling problem is a recursive optimal stopping problem, which is generally quite difficult to solve. However, we prove that the optimal sampling strategy is, in fact, a simple threshold policy where a new sample is taken whenever the instantaneous estimation error exceeds a threshold. This threshold remains a constant value that does not vary over time. By exploring the structure properties of the recursive optimal stopping problem, a low-complexity iterative algorithm is developed to compute the optimal threshold. This work generalizes previous research by incorporating both transmission errors and random transmission times into remote estimation. Numerical simulations are provided to compare our optimal policy with the zero-wait and age-optimal policies.