Motivated by interest in making delay announcements to arriving customers who must wait in call centers and related service systems, we study the performance of alternative real-time delay estimators based on recent customer delay experience. The main estimators considered are: (i) the delay of the last customer to enter service (LES), (ii) the delay experienced so far by the customer at the head of the line (HOL), and (iii) the delay experienced by the customer to have arrived most recently among those who have already completed service (RCS). We compare these delay-history estimators to the estimator based on the queue length (QL), which requires knowledge of the mean interval between successive service completions in addition to the queue length. We characterize performance by the mean squared error (MSE). We do analysis and conduct simulations for the standard GI/M/s multi-server queueing model, emphasizing the case of large s. We obtain analytical results for the conditional distribution of the delay given the observed HOL delay. An approximation to its mean value serves as a refined estimator. For all three candidate delay estimators, the MSE relative to the square of the mean is asymptotically negligible in the many-server and classical heavy-traffic limiting regimes.