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Request::send waits for Resolver before doing anything else, and the timeout a caller sets through Request::timeout is only armed later, in connect. A system resolver that never answers therefore holds the request for good: async_resolve has no deadline of its own, no timer covers the wait, and the callbacks queued in Resolver are never invoked. The proxy client reaches that path on every connectivity change, since connectivityChanged calls getProxyInfos, so a device coming back from sleep can sit there with no status, no listener and no error. getProxyInfos also builds a new Resolver each time and drops the previous one, discarding endpoints that were still perfectly usable. Resolution is then redone from scratch at the exact moment the network stack has just come up and is at its slowest. Give Resolver a deadline of its own, armed as soon as a query starts, and report timed_out to whoever is waiting. Let it also start from endpoints that were already resolved: those answer callbacks immediately so a connection begins without waiting, while the query still runs and replaces them as soon as it returns. An address that went stale in the meantime now costs one connection attempt, which Request retries against the pending query rather than reporting as a failure. A failed query no longer clears endpoints that are known to work, so a transient DNS outage leaves the client with something to connect to. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>