Three copper complexes with an N-methylated cryptand, LTEA, bearing a tris(2aminoethylamine moiety have been synthesized and compared. Two copper(II)-chloride complexes, [LTEACuCl](SbF 6 )(MeOH) and [LTEACuCl 2 ](MeCN) were characterized in solution and solid state by UV/Vis and X-ray crystallography. Both had square-based geometries with C 1 -symmetry and no encapsulation of the chloride ion. A Cu(II)-fluoride complex, in which the ligand is protonated, [LTEAHCuF](BF 4 ) 2 (MeCN) 0.5 , adopted C 3 -symmetry with complete encapsulation of the coordination sphere as characterized by UV/Vis, EPR and X-ray crystallography. Reactivity of the complexes with H 2 O 2 /Et 3 N was explored using UV/Vis and CSI-MS. Only the fluoride complex was found to form a Cu(II)hydroperoxo intermediate.