We study status updating under two-way delay in a system consisting of a sampler, a sink, and a controller residing at the sink. The controller drives the sampling process by sending request packets to the sampler. Upon receiving a request, the sampler generates a sample and transmits the status update packet to the sink. Transmissions of both request and status update packets encounter random delays. We develop optimal control policies to minimize the average age of information (AoI) using the tools of Markov decision processes in two scenarios. We begin with the system having at most one active request, i.e., a generated request for which the sink has not yet received a status update packet. Then, as the main distinctive feature of this paper, we initiate pipelined-type status updating by studying a system having at most two active requests. Furthermore, we conduct AoI analysis by deriving the average AoI expressions for the Zero-Wait-1, Zero-Wait-2, and Wait-1 policies. According to the Zero-Wait-1 policy, whenever a status update packet is delivered to the sink, a new request packet is inserted into the system. The Zero-Wait-2 policy operates similarly, except that the system can hold two active requests. According to the Wait-1 policy, whenever a status update packet is delivered to the sink, a new request is sent after a waiting time which is a function of the current AoI. Numerical results illustrate the performance of each status updating policy under varying system parameter values.