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A messages array containing null (or any non-object entry, e.g. [null] or [42]) passed every existing entry guard in chat.ts (#5110/#6402/#6407/#6412) and reached downstream translators/session helpers that read `.role` / `.content` directly off each entry (openai-to-claude.ts, sessionManager.ts, contextManager.ts's fixToolPairs), crashing with a raw TypeError and surfacing as an HTTP 500 instead of a clean 400. The route's Zod schema is intentionally wide (z.array(z.unknown())), so this shape check belongs in the handler's guard chain. Adds one more entry-shape guard clause to the same chokepoint, rejecting the request with a clear 400 before any routing or upstream call. Regression test: tests/unit/chat-messages-entry-objects-12643.test.ts PR #12644 (@soroush5) proposed this exact fix but was closed without merging on 2026-09-12; this re-implements it fresh against the current tip using the same guard shape and error message. Originally-proposed-by: @soroush5 in #12644 Co-authored-by: soroush5 <mrsoroushahmadi@gmail.com>