Abstract Theranostic prodrugs that can precisely monitor drug activation with synergistic therapeutic effects are highly desirable for personalized medicine. In this study, a theranostic heterodimeric prodrug, CyNH‐SS‐DOX, with synchronous and independent dual‐channel fluorescence turn‐on and dual‐prodrug activation for synergistic cancer therapy is developed. A hemicyanine fluorescent drug, CyNH 2 , with good therapeutic effects found in this work, is conjugated to doxorubicin (DOX) through a disulfide linker to form CyNH‐SS‐DOX. Before activation, both the fluorescence of DOX and CyNH 2 are in the off state and the toxicity is low. In the presence of intracellular glutathione, both the fluorescence of DOX and CyNH 2 at different channels are turned on. Meanwhile, DOX and CyNH 2 are activated in a synergistic anticancer effect. It is believed that CyNH‐SS‐DOX is promising for monitoring prodrug activation in dual‐fluorescence channels and for enhancing therapeutic efficacy with few side effects.