The effects of executive load on working memory performance during sleep inertia after morning or afternoon naps were assessed using a mixed design with nap/wake as a between-subjects factor and morning/afternoon condition as a within-subject factor. Thirty-two healthy adults (mean 22.5 ± 3.0 years) attended two laboratory sessions after a night of restricted sleep (6 hrs), and at first visit, were randomly assigned to the Nap or Wake group. Working memory (n-back) and subjective workload were assessed approximately 5 and 25 minutes after 90-minute morning and afternoon nap opportunities and at the corresponding times in the Wake condition. Actigraphically assessed nocturnal sleep duration, subjective sleepiness, and psychomotor vigilance performance before daytime assessments did not vary across conditions. Afternoon naps showed shorter EEG assessed sleep latencies, longer sleep duration, and more Slow Wave Sleep than morning naps. Working memory performance deteriorated, and subjective mental workload increased at higher executive loadings. After afternoon naps, participants performed less well on more executive-function intensive working memory tasks (i.e., 3-back), but waking and napping participants performed equally well on simpler tasks. After some 30 minutes of cognitive activity, there were no longer performance differences between the waking and napping groups. Subjective Task Difficulty and Mental Effort requirements were less affected by sleep inertia and dissociated from objective measures when participants had napped in the afternoon. We conclude that executive functions take longer to return to asymptotic performance after sleep than does performance of simpler tasks which are less reliant on executive functions.