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Here, we report a rapid four\u2010step synthesis of a well\u2010defined pyridyl hexa\u2010amide cage based on a readily accessible benzylic tris\u2010aniline platform. Microwave\u2010assisted imine condensation enables fast cage assembly, while subsequent Pinnick oxidation converts the dynamic architecture into a permanently locked\n                    <jats:italic>C<\/jats:italic>\n                    <jats:sub>3<\/jats:sub>\n                    \u2010symmetric host. Single\u2010crystal x\u2010ray diffraction reveals a rigid cavity lined with six inward\u2010oriented N\u2013H donors, generating a confined hydrogen\u2010bonding environment suitable for anion recognition. In DMSO, mono\u2010 and dicarboxylate guests bind in a fast\u2010exchange regime with comparable apparent affinities. In contrast, a symmetry\u2010matched tricarboxylate (nitrilotripropionate, NTP) induces the formation of a discrete 1:1 host\u2013guest complex displaying distinct titration behavior and confirmed crystallographically. Control experiments with a more rigid tricarboxylate (aluminon) revealed no detectable binding under comparable conditions, suggesting that guest conformational adaptability also contributes to complex formation. These observations highlight how rigidification and geometric complementarity within a confined cavity can influence host\u2010guest recognition behavior in solution.\n                  <\/jats:p>","DOI":"10.1002\/chem.71335","type":"journal-article","created":{"date-parts":[[2026,6,29]],"date-time":"2026-06-29T11:26:44Z","timestamp":1782732404000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Rapid Assembly of a Covalently Locked Organic Cage Revealing Symmetry\u2010Matched Guest Recognition"],"prefix":"10.1002","volume":"32","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2460-2607","authenticated-orcid":false,"given":"Melvin","family":"Raulin","sequence":"first","affiliation":[{"name":"Institut Lavoisier de Versailles, UMR8180 Universit\u00e9 Paris\u2010Saclay, UVSQ, CNRS  Versailles France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arnaud","family":"Tillet","sequence":"additional","affiliation":[{"name":"Institut Lavoisier de Versailles, UMR8180 Universit\u00e9 Paris\u2010Saclay, UVSQ, CNRS  Versailles France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vincent","family":"Barbier","sequence":"additional","affiliation":[{"name":"Evotec ID (Lyon) SAS  Marcy l'Etoile France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Flavien","family":"Bourdreux","sequence":"additional","affiliation":[{"name":"Institut Lavoisier de Versailles, UMR8180 Universit\u00e9 Paris\u2010Saclay, UVSQ, CNRS  Versailles France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9003-0670","authenticated-orcid":false,"given":"R\u00e9gis","family":"Guillot","sequence":"additional","affiliation":[{"name":"Institut De Chimie Mol\u00e9culaire Et Des Mat\u00e9riaux d'Orsay, UMR 8182 CNRS, Universit\u00e9 Paris\u2010Saclay  Orsay France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00e9r\u00f4me","family":"Marrot","sequence":"additional","affiliation":[{"name":"Institut Lavoisier de Versailles, UMR8180 Universit\u00e9 Paris\u2010Saclay, UVSQ, CNRS  Versailles France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4519-8028","authenticated-orcid":false,"given":"Olivier R. 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