The visualization of polymer deformation using microcapsules filled with charge-transfer complex precursors is reported. Poly(urea-formaldehyde) microcapsules filled with toluene and either hexamethylbenzene as donor or chloranil as acceptor were prepared by in situ polymerization of an oil-in-water emulsion. The resulting microcapsules were incorporated in a poly(dimethylsiloxane) matrix by dispersing them in the monomer and subsequent curing. The microcapsules were shown to rupture when the polymer was placed under mechanical forces (i.e., tensile and compression) such that the donor and the acceptor are released into the polymeric matrix, where their combination to a charge-transfer complex results in a pronounced yellow-to-red color change. The factors influencing the extent of the color change (composition and mechanical strain) were investigated and a deformation threshold seems to be present. The new damage-sensing materials may be useful for a range of applications and the general concept applied seems to be readily applicable to other host polymers.