Functional neuroimaging comparisons of context and item memory frequently implicate the left prefrontal cortex (PFC) during the recovery of contextually specific memories. However, because cues and probes are often presented simultaneously, this activity could reflect operations involved in planning retrieval or instead reflect later operations dependent upon the memory probes themselves, such as evaluation of probe-evoked recollections. More importantly, planning-related activity, wherein subjects reinstate details outlining the nature of desired remembrances, should occur in response to contextual memory cues even before retrieval probes are available. Using event-related functional magnetic resonance imaging, we tested this by dissociating cue- from probe-related activity during context memory for pictures. Cues forewarning contextual memory demands yielded more activity than those forewarning item memory in the left lateral precentral gyrus, midline superior frontal gyrus, and right frontopolar cortex. Thus, these anticipatory, cue-based activations indicated whether upcoming probe decisions would require contextually specific memories or not. In contrast, the left dorsolateral/midventrolateral and anterior ventrolateral PFC areas did not show differential activity until the probes were actually presented, demonstrating greater activity for context than for item memory probes. Direct comparison of proximal left PFC regions demonstrated qualitatively different response profiles across cue versus probe periods for lateral precentral versus dorsolateral regions. These results potentially isolate contextual memory-planning-related processes from subsequent processes such as the evaluation of recollections, which are necessarily dependent on individual probe features. They also demonstrate that contextual remembering recruits multiple, functionally distinct PFC processes.