With the rise of large language models, agentic systems are becoming increasingly autonomous, as they write code, call tools, revise prompts, and propose modifications to their own components. This autonomy raises a fundamental question for safe self-improvement: can an automated gate like a reward model or an automated reviewer reliably decide whether a proposed update should be accepted? The difficulty is structural. The gate must be a terminating, computable procedure, while the property we ultimately care about, namely whether an update is a genuine semantic improvement, depends on potentially unbounded program behavior. We formalize this mismatch by modeling agents as programs and defining improvement in terms of a semantic score that need not be computable. We study two evaluation abstractions. The first is a certifier that approves or rejects an update. The second is a search procedure that, given access to a proposal generator, attempts to output some improving candidate if one exists. We show that, in the fully general setting, no terminating procedure can simultaneously guarantee reliability (never accepting a non-improvement) and non-conservatism (never missing an available improvement): self-referential constructions can force any such gate or searcher to fail. Randomized gates with bounded error face the same limit. We then identify a standard decidable regime used in practice (bounded evaluation and a finite proposal budget) under which exhaustive simulation yields a terminating search procedure with the desired guarantees. We also show the limit of this recovery: a chain of accepted updates can raise the bounded score in every round while the true score falls. Our results draw a boundary between unbounded, universal settings where correctness guarantees collapse and bounded settings where they can be recovered by design.