N-acyl-7-nitroindolines are light-responsive compounds capable of acylating nucleophiles in inert, aprotic solvents under neutral conditions when triggered by near UV light. These compounds have previously served as linkers in solid-phase synthesis to generate amides and thioesters. In exploring their potential in glycopeptide synthesis, we constructed two model glycopeptides derived from Mucin 1, featuring tumor-specific antigens GalNAcα (Tn) or NeuNAcα(2,6)GalNAcα (STn). This was achieved via solid phase peptide synthesis (SPPS) utilizing the Fmoc/tBu strategy, employing a 7-nitroindoline linker attached to the resin. This linker facilitated the direct photorelease of protected glycopeptide acids and amides from the solid support into the solution. Alternatively, glycopeptides with a C-terminal 7-nitroindoline moiety were subjected to photochemical reactions in solution, enabling the synthesis of the same peptide derivatives, and additionally, glycopeptide phenyl thioesters. We showcase that N-glycopeptidyl-7-nitroindolines can be effectively transformed into protected glycopeptide acids, amides, and thioesters, thereby broadening the applicability of N-acyl-7-nitroindoline linkers in SPPS.