The FX-construction was proposed in 1996 by Kilian and Rogaway as a generalization of the DESX scheme. The construction increases the security of an n-bit core block cipher with a $$\kappa $$ -bit key by using two additional n-bit masking keys. Recently, several concrete instances of the FX-construction were proposed, including PRINCE, PRIDE and MANTIS (presented at ASIACRYPT 2012, CRYPTO 2014 and CRYPTO 2016, respectively). In this paper, we devise new cryptanalytic time–memory–data trade-off attacks on FX-constructions. By fine-tuning the parameters to the recent FX-construction proposals, we show that the security margin of these ciphers against practical attacks is smaller than expected. Our techniques combine a special form of time–memory–data trade-offs, typically applied to stream ciphers, with a cryptanalytic technique by Fouque, Joux and Mavromati. In the final part of the paper, we show that the techniques we use in cryptanalysis of the FX-construction are applicable to additional schemes. In particular, we use related methods in order to devise new time–memory trade-offs for solving the affine equivalence problem. In this problem, the input consists of two functions $$F,G: \{0,1\}^n \rightarrow \{0,1\}^n$$ , and the goal is to determine whether there exist invertible affine transformations $$A_1,A_2$$ over $$GF(2)^n$$ such that $$G = A_2 \circ F \circ A_1$$ .