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Both API requests and binary downloads retry against a hard-coded IP when the attempt via hostname fails. Both then overwrote the first error with the fallback's, so only the last failure was reported. That discarded the diagnosis. During the Firewall Mode incident the hostname attempt was denied locally - WSAEACCES, "An attempt was made to access a socket in a way forbidden by its access permissions", which means the host is blocking ctrld - while the direct-ip fallback failed with an unreachable IPv6 route. What surfaced to the operator was "dial tcp6: no route to host", pointing at a routing problem that did not exist, while the WSAEACCES that named the real cause was visible only in debug logs. Report both failures instead, keeping the error chain intact so errors.Is still matches either one. Also switch the final wrap in doWithRetry from %v to %w, which had been flattening the chain even when a single error was reported. Add coverage for both paths, including that the fallback is still attempted and that a successful fallback returns no error. This also changes retry classification, which is worth stating explicitly because it is not obvious from "report both errors". processCDFlags decides whether to keep backing off with errUrlNetworkError, which uses errors.As - and errors.As returns the first match in the tree. Wrapping the hostname attempt first therefore hands the predicate that attempt's failure, where previously only the fallback's error survived to be classified. The effect is intended. A locally denied socket (WSAEACCES) is not a transient network error, so preflight now fails fast and reports instead of retrying against a firewall that is not going to clear on its own - the incident logged 256 retry cycles doing exactly that. The case that justifies retrying forever, a network unreachable on both attempts at boot, is unchanged. Both classifications are pinned by tests, along with the wrap order they depend on at each composition site, so reversing it fails loudly rather than silently restoring the old behaviour.