Certifying compilation allows a compiler to produce annotations that prove that target code abides by a specified safety policy. An independent verifier can check the code without needing to trust the compiler. For such a system to be generally useful, the safety policy should be expressive enough to allow different compilers to effectively produce certifiable code. In this work, we use our experience in writing a certifying compiler to suggest general design principles that should allow concise yet expressive certificates. As an extended example, we present our compiler's translation of the control flow of Popcorn, a high-level language with function pointers and exception handlers, to TALx86, a typed assembly language with registers, a stack, memory, and code blocks. This example motivates techniques for controlling certificate size and verification time. We quantify the effectiveness of techniques for reducing the overhead of certifying compilation by measuring the effects their use has on a real Popcorn application, the compiler itself. The selective use of these techniques, which include common-subexpression elimination of types, higher-order type abbreviations, and selective re-verification, can change certificate size and verification time by well over an order of magnitude. We consider this report to be the first quantitative study on the practicality of certifying a real program using a type system not specifically designed for the compiler or source language.