Single fiber mechanical testing is challenging to perform, especially when the diameter is as small as tens of micrometers. For this reason, real‐time observations of crack propagation mechanisms have been rarely been investigated experimentally. This article presents experimental and numerical investigations of fracture of monofilamentary high performance polyamide 66 fibers. Their engineering stress–strain curves are compared. The mechanisms of failure starting from crack initiation until the final brittle fracture are studied by in situ tests in Scanning Electron and optical microscopes. Finite element modeling at the individual fiber scale has been performed in three‐dimensional (3D), as a reverse engineering method. The compliance method was used to determine the crack depth that triggers the final failure. The fracture toughness was numerically determined using the J‐integral concept, accounting for the geometry of the crack front (3D) together with plastic deformation. 3D meshes were designed especially from postmortem observations. The average value deduced was about 47 ± 7 kJ m−2, which will be discussed with other estimates using linear elastic fracture mechanics.