Speech com­pre­hen­sion in mul­ti-talk­er sit­u­a­tions is a noto­ri­ous real-life chal­lenge, par­tic­u­lar­ly for old­er lis­ten­ers. Younger lis­ten­ers exploit stim­u­lus-inher­ent acoustic detail, but are they also active­ly pre­dict­ing upcom­ing infor­ma­tion? And fur­ther, how do old­er lis­ten­ers deal with acoustic and pre­dic­tive infor­ma­tion? To under­stand the neur­al dynam­ics of lis­ten­ing dif­fi­cul­ties and accord­ing lis­ten­ing strate­gies, we con­trast­ed neur­al respons­es in the alpha-band (~10 Hz) in younger (20−30 years, n = 18) and healthy old­er (60−70 years, n = 20) par­tic­i­pants under chang­ing task demands in a two-talk­er par­a­digm. Elec­troen­cephalo­grams were record­ed while humans lis­tened to two spo­ken dig­its against a dis­tract­ing talk­er and decid­ed whether the sec­ond dig­it was small­er or larg­er. Acoustic detail (tem­po­ral fine struc­ture) and pre­dic­tive­ness (the degree to which the first dig­it pre­dict­ed the sec­ond) var­ied orthog­o­nal­ly. Alpha pow­er at wide­spread scalp sites decreased with increas­ing acoustic detail (dur­ing tar­get dig­it pre­sen­ta­tion) but also with increas­ing pre­dic­tive­ness (in-between tar­get dig­its). For old­er com­pared to younger lis­ten­ers, acoustic detail had a stronger impact on task per­for­mance and alpha pow­er mod­u­la­tion. This sug­gests that alpha dynam­ics plays an impor­tant role in the changes in lis­ten­ing behav­ior that occur with age. Last­ly, alpha pow­er vari­a­tions result­ing from stim­u­lus manip­u­la­tions (of acoustic detail and pre­dic­tive­ness) as well as task-inde­pen­dent over­all alpha pow­er were relat­ed to sub­jec­tive lis­ten­ing effort. The present data show that alpha dynam­ics is a promis­ing neur­al mark­er of indi­vid­ual dif­fi­cul­ties as well as age-relat­ed changes in sen­sa­tion, per­cep­tion, and com­pre­hen­sion in com­plex com­mu­ni­ca­tion situations.