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Discord (and similar platforms) can serve a PNG image cached as discord_xxx.webp because the CDN reports content_type=image/webp for proxied stickers, custom emoji, and certain bot-uploaded images even when the actual bytes are PNG. Hermes' agent.image_routing._guess_mime trusted the file suffix and declared media_type=image/webp to Anthropic, which strict-validates and returns: HTTP 400 messages.N.content.M.image.source.base64: The image was specified using the image/webp media type, but the image appears to be a image/png image The Discord image attachment never reaches the model; the whole turn fails with no salvage path. Fix: sniff magic bytes in _file_to_data_url before declaring MIME. Suffix-based detection is kept as a fallback when bytes aren't available. New helper _sniff_mime_from_bytes covers PNG, JPEG, GIF, WEBP, BMP, and HEIC/HEIF. Tests: - Two existing tests asserted the old broken behaviour (PNG bytes in a .jpg/.webp file should report jpeg/webp); rewritten with real jpeg/webp magic bytes so they still cover suffix-aligned cases. - New regression test test_mime_sniff_overrides_misleading_extension reproduces the exact Discord scenario (PNG bytes, .webp suffix) and asserts the data URL comes back as image/png. All 28 tests in tests/agent/test_image_routing.py pass.