3) Bioorthogonal linkers are stable to commonly encountered CPS conditions (e.g., resin cleavage, ligation, and desulfurization) 4) Removal of bioorthogonal linkers is chemoselective, traceless, and efficient 5) Flexible positioning of bioorthogonal linkers within peptide sequences (e.g., placement not restricted to termini or infrequent amino acids) Here, we describe Click-Assisted NCL (CAN), which meets all these criteria by combining a traceless "helping hand" Lys linker (Ddap) with the bioorthogonal strained-click pair dibenzocyclooctyne (DBCO) and azide (Scheme 1B). In the CAN strategy, peptide segments are first coupled with a Ddap linker on a Lys sidechain onresin during SPPS before functionalization with either DBCO or azide. After resin cleavage and HPLC purification, the DBCO/azide-bearing peptides are combined for SPAAC. The resultant triazole linkage effectively templates the C-terminal thioester and N-terminal thiol for ligation, increasing their effective concentration and allowing NCL to proceed with high efficiency. After ligation, mild hydroxylamine treatment chemoselectively removes the templating linkers, affording the native ligated peptide.