"And they presumed [va-yaʿpilu]" — it is a term of darkness, like "and they darkened [va-yaʾafilu]," because the wicked one is called darkness, as it is said, "And their deeds [their eyes] are in the dark" (Isaiah 29:15). And why? Because they did the thing presumptuously, for Moses was restraining them not to go and enter the Land, and it was impossible to nullify the decree; yet they were trusting to nullify it by what they had said, "for we have sinned." Therefore it is said, "And they presumed," as it is said, "but the fool walks in darkness" (Ecclesiastes 2:14).
Why the Presumptuous Walked in Darkness Up the Mountain
Midrash Aggadah, Numbers 14:44
ויעפילו. לשון חשך הוא, כמו ויאפילו לפי שהרשע נקרא חשך, שנאמר והיה במחשך (עיניהם) [מעשיהם] (ישעיה כ"ט ט"ו), ולמה שעשו הדבר בזדון, שמשה היה מונעם שלא ילכו ויכנסו בארץ, ואי אפשר לבטל הגזירה, והם היו בוטחים לבטל במה שאמרו כי חטאנו לך, לכך נאמר ויעפילו, כמה דתימא והכסיל בחשך הולך (קהלת ב' י"ד):