This study investigated interactive effects of stress and task difficulty on working memory and cortico-cortical communication during memory encoding. Thirty-eight adolescent participants (mean age of 15.7 ± 1.5 years) completed easy and hard working memory tasks under low- and high-stress conditions. We analyzed the accuracy and reaction time (RT) of working memory performance and inter- and intrahemispheric electroencephalogram coherences during memory encoding. Working memory accuracy was higher, and RT shorter, in the easy versus the hard task. RT was shorter under the high-stress (TENS) versus low-stress (no-TENS) condition, while there was no difference in memory accuracy between the two stress conditions. For electroencephalogram coherence, we found higher interhemispheric coherence in all bands but only at frontal electrode sites in the easy versus the hard task. On the other hand, intrahemispheric coherence was higher in the left hemisphere in the easy (versus hard task) and higher in the right hemisphere (with one exception) in the hard (versus easy task). Inter- and intracoherences were higher in the low- versus high-stress condition. Significant interactions between task difficulty and stress condition were observed in coherences of the beta frequency band. The difference in coherence between low- and high-stress conditions was greater in the hard compared with the easy task, with lower coherence under the high-stress condition relative to the low-stress condition. Stress seemed to cause a decrease in cortical network communications between memory-relevant cortical areas as task difficulty increased.