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The use of real\u2010time mass spectrometry (PSI\u2010ESI\u2010MS) coupled to <jats:italic>tandem<\/jats:italic> mass spectrometry and infrared multiple photon dissociation (IRMPD) allowed the differentiation of the species observed during the synthesis of benzoxazines in these different conditions. The results suggest that formic acid promotes the formation of aniline and phenol condensation products (<jats:bold>IC<\/jats:bold> and <jats:bold>IIC<\/jats:bold>) by protecting the aniline amino group and enhancing the formaldehyde electrophilicity. The results also suggest that although the presence of acid allow a more efficient potential energy landscape to be accessed, the last cyclization step for the formation of benzoxazines cannot be mediated by the protonation route intermediate (<jats:bold>ROP Bz<\/jats:bold>). 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