Compiler optimizations, although reducing the execution times of programs, raise issues in static WCET estimation techniques and tools. Flow facts, such as loop bounds, may not be automatically found by static WCET analysis tools after aggressive code optimizations. In this paper, we explore the use of iterative compilation (WCET-directed program optimization to explore the optimization space), with the objective to (i) allow flow facts to be automatically found and (ii) select optimizations that result in the lowest WCET estimates. We also explore to which extent code outlining helps, by allowing the selection of different optimization options for different code snippets of the application.