Software-Based Self-Test (SBST) approaches have shown to be an effective solution to detect permanent faults, both at the end of the production process, and during the operational phase. However, when Very Long Instruction Word (VLIW) processors are addressed these techniques require some optimization steps in order to properly exploit the parallelism intrinsic in these architectures. In this chapter we present a new method that, starting from previously known algorithms, automatically generates an effective test program able to still reach high fault coverage on the VLIW processor under test, while minimizing the test duration and the test code size. Moreover, using this method, a set of small SBST programs can be generated aimed at the diagnosis of the VLIW processor. Experimental results gathered on a case study show the effectiveness of the proposed approach.