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The deadline in Opengraph::Fetch started after the lookup of the pasted host, and an unfurl looks up more hosts outside any fetch: the canonical URL's, and the image's, once to check its content type and again to validate it. Each of those waits as long as the resolver takes to give up. Move the deadline up to UnfurlLinksController, around everything the link leads to; Opengraph::Fetch keeps its per-operation timeouts and makes no retries. Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com> Claude-Session: https://claude.ai/code/session_01Bj8KnxpTf9sj2Ysa8aLAVa