This paper analytically studies the effect of radial engagement on chatter stability when the flexibility is perpendicular to the feed motion, with thin-walled part milling being the most relevant industrial case. By studying the mean directional factor and its harmonics, the superior stability of the up-milling strategy over down-milling for both Hopf and flip chatter is demonstrated. The optimal engagement for a theoretical infinite stable depth of cut Hopf is obtained, as well as the expressions for the critical depth of cut. For flip chatter, three different cutting zones with different lobe shapes can occur depending on the radial engagement. It is also shown that while flip chatter cannot be completely eliminated by tuning the radial engagement alone, an engagement can be found in up-milling that maximises stability. Finally, the findings are validated through experimental tests.