Technologies for defeating secure enclave side-channel attacks include a computing device having a processor with secure enclave support. The computing device instruments an executable binary with multiple gadgets, a fault-generating function, and at least one invocation of the fault-generating function. The computing device executes the instrumented executable binary within a secure enclave. During execution of the instrumented binary, each gadget may be located at a different memory page of the secure enclave. The computing device invokes the fault-generating function, which selects a random sequence of the gadgets and executes the random sequence of gadgets. The processor may generate a page fault in response to executing each of the gadgets. Each gadget may generate one or more data accesses to memory pages within the secure enclave. The processor may generate a page fault in response to each of the data accesses. Other embodiments are described and claimed.