Tetra-urea calix[4]pyrroles dimerize into homocapsules either by including 4,4'-bipyridine N-N'-dioxide or through pair-wise encapsulation of trimethylamine-N-oxide [1]. On the other hand, chloroform is a typical guest for tetra-urea calix[4]arene capsules. In this presentation, I will introduce the assembly of dimeric capsules based on tetra-urea calix[4]pyrrole scaffolds. I will briefly comment on the use of molecular rulers to explore their cavity dimensions and adaptability [2]. I will also discuss very recent findings on the light-controlled assembly and cavity size modulation using hydrogen-bonded tetraurea capsular aggregates having appended diphenyl-azo-groups [3]. Finally, I will disclose the use of a hybrid assembly consisting of a tetraurea-calix[4]pyrrole and a tetraurea-calix[4]arene in the construction of mechanically interlocked capsules displaying anisotropic functionalized interiors.