diff --git a/esphome/net_retry.py b/esphome/net_retry.py
index 3f4a507418..f783f77607 100644
--- a/esphome/net_retry.py
+++ b/esphome/net_retry.py
@@ -25,9 +25,21 @@ def _is_permanent_dns_failure(e: BaseException) -> bool:
 
     EAI_AGAIN ("temporary failure in name resolution", the flaky container
     resolver case) stays retryable; only hard resolution failures like
-    NXDOMAIN count. requests wraps urllib3's MaxRetryError, which carries
-    the underlying NameResolutionError in its ``reason`` attribute rather
-    than the __cause__ chain, so attributes and args are walked as well.
+    NXDOMAIN count. Everything except EAI_AGAIN is treated as permanent:
+    deliberately narrower than git.py, which retries NXDOMAIN too. Codes
+    like EAI_NONAME can occur during a brief network outage, but a 6s
+    backoff rarely outlives one, and permanent means callers with a cached
+    copy fall back to it immediately instead of sleeping first (the
+    offline-build case). The trade-off is that a hard resolver failure on
+    a first download fails without retrying, same as before retries
+    existed.
+
+    Only the deliberate chain is walked: ``__cause__``, ``args`` (requests
+    wraps MaxRetryError as ``ConnectionError(e)`` without ``from``) and
+    urllib3 MaxRetryError's ``reason`` attribute (NameResolutionError never
+    lands on the cause chain). Implicit ``__context__`` is skipped so a
+    resolution failure from an unrelated earlier attempt cannot reclassify
+    an error it did not cause.
     """
     import socket
 
@@ -37,23 +49,17 @@ def _is_permanent_dns_failure(e: BaseException) -> bool:
         exc = stack.pop()
         if id(exc) in seen:
             continue
-        if isinstance(exc, socket.gaierror):
-            # Everything except EAI_AGAIN is treated as permanent. This is
-            # deliberately narrower than git.py, which retries NXDOMAIN
-            # too: codes like EAI_NONAME can occur during a brief network
-            # outage, but a 6s backoff rarely outlives one, and permanent
-            # means callers with a cached copy fall back to it immediately
-            # instead of sleeping first (the offline-build case). The
-            # trade-off is that a hard resolver failure on a first
-            # download fails without retrying, same as before retries
-            # existed.
-            return exc.errno != socket.EAI_AGAIN
+        if (
+            isinstance(exc, socket.gaierror)
+            and exc.errno is not None
+            and exc.errno != socket.EAI_AGAIN
+        ):
+            return True
         seen.add(id(exc))
         stack.extend(
             nxt
             for nxt in (
                 exc.__cause__,
-                exc.__context__,
                 getattr(exc, "reason", None),  # urllib3 MaxRetryError
                 *exc.args,
             )
diff --git a/tests/unit_tests/test_net_retry.py b/tests/unit_tests/test_net_retry.py
index 700256d9ff..d915a0ef9b 100644
--- a/tests/unit_tests/test_net_retry.py
+++ b/tests/unit_tests/test_net_retry.py
@@ -74,6 +74,39 @@ class TestIsTransientDownloadError:
 
         assert is_transient_download_error(chained)
 
+    def test_implicit_context_does_not_reclassify(self) -> None:
+        """A resolution failure from an unrelated earlier attempt reaches the
+        final error only via implicit __context__ (raise inside an except
+        block); it must not turn a genuine connection reset permanent."""
+        try:
+            try:
+                raise socket.gaierror(socket.EAI_NONAME, "first attempt")
+            except socket.gaierror:
+                raise req.ConnectionError("reset by peer") from None
+        except req.ConnectionError as reset:
+            assert reset.__context__ is not None
+            assert is_transient_download_error(reset)
+
+    def test_gaierror_without_errno_stays_transient(self) -> None:
+        """A gaierror carrying no EAI code cannot prove a hard failure."""
+        chained = req.ConnectionError("resolution failed")
+        chained.__cause__ = socket.gaierror("no errno")
+
+        assert is_transient_download_error(chained)
+
+    def test_mixed_chain_hard_failure_wins(self) -> None:
+        """EAI_AGAIN in the chain does not mask a hard failure elsewhere."""
+        again = socket.gaierror(socket.EAI_AGAIN, "temporary failure")
+        hard = socket.gaierror(socket.EAI_NONAME, "unknown host")
+
+        outer = req.ConnectionError(hard)
+        outer.__cause__ = again
+        assert not is_transient_download_error(outer)
+
+        outer = req.ConnectionError(again)
+        outer.__cause__ = hard
+        assert not is_transient_download_error(outer)
+
     def test_dns_walk_survives_exception_cycles(self) -> None:
         """A cyclic cause chain must terminate (and stay transient when no
         resolution failure is present)."""