This study investigates modeling, estimation and optimization of destructive degradation tests (DDTs) for highly reliable products with random initial degradation values. It is common to observe that the degradation paths of distinct products start from different values specified by a random variable. The random initial value introduces additional uncertainties to the degradation of the product. In this study, Wiener-process-based degradation models are developed for products with random initial values. We first consider a DDT without stress acceleration. In a DDT, the measurement of the degradation destroys a test unit and, thus, only one measurement is available for each unit. Closed-form maximum likelihood (ML) estimators are derived. Then, an accelerated DDT (ADDT) is considered. Based on these results, we investigate optimal designs of both DDT and ADDT with the objective of minimizing the asymptotic variance of the estimated $p$ th-quantile of the failure time distribution under use conditions. The optimal test plans have to be obtained through a numerical approach. Optimality of the plans is verified by the general equivalence theorem. An adhesive bond example with real degradation data is analyzed to show the performance of the proposed methods.