Regenerable surfaces and reversible attachment of nanostructures onto them is an important aim in nanotechnology. Reversible attachment of nanostructures at molecular printboards was illustrated by the adsorption and desorption of β-cyclodextrin (β-CD)-functionalized nanoparticles onto and from stimuli-responsive preadsorbed ferrocenyl-functionalized poly(propylene imine) dendrimers at a β-CD self-assembled monolayer (SAM). Electrochemical oxidation of the ferrocenyl endgroups was employed to induce desorption of nanostructures from the β-CD SAMs. A combined surface plasmon resonance spectroscopy and electrochemistry setup was used to monitor the in situ adsorption and desorption of ferrocenyl dendrimers and β-CD-functionalized Au nanoparticles (CD-Au, d 2.8 nm) onto and from the molecular printboard. In the case of the larger β-CD-functionalized silica nanoparticles (CD-SiO2, d 60 nm), ultrasonication was used to reduce the desorption time. By electrochemical oxidation applied to a specific area of a nanoparticle layer, local desorption of nanoparticles was observed. In the nonoxidized area, nanoparticles remained robustly attached to the surface, whereas nanoparticles on the electrochemically oxidized area were completely removed.