We have synthesized and characterized a new family of nematic all-aromatic polyesteramide thermosets based on 6-hydroxy-2-naphthoic acid (HNA), terephthalic acid (TA), and 4-acetamidophenol (AAP). In order to incorporate a high concentration of the amide-based monomer (AAP), the melt transition (T_K-N) and melt viscosity had to be lowered in order to maintain melt processable intermediates. Precursor thermoplastic reactive oligomers, end-capped with phenylethynyl functionalities, were prepared using standard melt condensation techniques with a target M_n of 1000–9000 g mol⁻¹. The reactive oligomers with 20–30 mol% AAP could easily be processed into films, and the films exhibit good tensile properties in terms of tensile strength (70–80 MPa) and elongation at break (7–10%). A glass transition of 191°C could be obtained when a 1000 g mol⁻¹ oligomer (HNA/TA/AAP(20)–1 K) was thermally cross-linked. When the AAP concentration reaches 35 mol%, the rigidity of the backbone and the hydrogen bonding interactions are enhanced, which make HNA/TA/AAP(35) polymers difficult to process.