Dental assemblies and related methods of making are provided. The dental assemblies include a dental article with a bonding surface an adhesive having both a compressible material and at least one hardenable dental composition extending across the bonding surface. The compressible material is coupled to the dental article by a first quantity of hardened dental composition extending at least partially through the compressible material and contacting the bonding surface. The hardened dental composition extends over less than the entire bonding surface. Adjacent portions of the compressible material contain a second quantity of unhardened dental composition, preserving flexibility of the compressible material. Advantageously, this configuration was found to enhance bond reliability and facilitate manufacturing.