In recent years, the study of Galactic cosmic ray leptons has advanced significantly, largely due to measurements of absolute fluxes of positrons and electrons by AMS-02, and to the direct measurements of the total lepton flux above TeV energies by DAMPE and CALET. In this talk, we discuss how these results refine our models of cosmic ray propagation and contribute to resolving outstanding questions about the sources of high-energy cosmic rays. Moreover, the observations of TeV halos surrounding pulsars provide crucial insights into the mechanisms of particle acceleration in pulsar wind nebulae and their release in the interstellar medium. By presenting the latest results from high-energy gamma-ray observatories, we explore how these findings contribute to resolving outstanding questions about the sources of high-energy cosmic ray leptons.