Listening in everyday life requires attention to be deployed dynamically - when listening is expected to be difficult and when relevant information is expected to occur - to conserve mental resources. Conserving mental resources may be particularly important for older adults who often experience difficulties understanding speech. We use electro- and magnetoencephalography to investigate the neural and behavioral mechanics of dynamic attention regulation during listening and the effects that aging may have on these. We show that neural alpha oscillatory activity indicates when in time attention is deployed (Experiment 1) and that deployment depends on listening difficulty (Experiment 2). Older adults also show successful attention regulation, although younger adults appear to utilize timing information a bit differently compared to older adults. We further show that the recruited brain regions differ between age groups. Superior parietal cortex is involved in attention regulation in younger adults, whereas posterior temporal cortex is more involved in older adults (Experiment 3). This difference in the sources of alpha activity across age groups was only observed when a task was performed, and not for alpha activity during resting-state recordings (Experiment S1). In sum, our study suggests that older adults employ different neural control strategies compared to younger adults to regulate attention in time under listening challenges.