Les Écorchés - S2-E7
Stupidity: The highly trained, elite security officer who tracks Angela down to the backups knows exactly what she is, how dangerous she is, and what she's capable of, but still drops his guard, flirts with her, lets her get up close and personal with him, and as a result gives her a clear window to grab his grenade to blow up herself, him, and all the backups.
Chapter Eight: The Battle of Starcourt - S3-E8
Stupidity: SPOILERS AHEAD: It has been a good minute between Hopper killing Grigory and Joyce turning the key. He could have used that time to run as quickly as he can towards her, instead of staring at her for 30 seconds. Also, Dustin didn't have to yell (through the radio) so panicky yet about closing the gate. While Mind Flayer was killing Billy, El and other kids could have used the time to run further again and get another 2-3 minutes, in that time Hopper would surely come to a safe place.
Stupidity: While discussing his arrest with Emily, Seth mentions that he didn't tell the arresting officer that he works for Kirkman. As the White House's liaison to the media, Seth has a high degree of visibility; it would extremely difficult, if not downright impossible, to keep his place of employment concealed from the police for very long in the time between his booking and arraignment and when Kendra bails him out the following day.
Stupidity: Eve, the assassin trying to kill the Senator, tells Cole to move or she'll shoot through him, rather than just shooting him. She already killed an agent by shooting him in the back and had plenty of time to just shoot Cole, so there's no reason for her to avoid killing him.