diff --git a/tests/tools/test_url_safety.py b/tests/tools/test_url_safety.py
index 62b684d535..ca004c3d60 100644
--- a/tests/tools/test_url_safety.py
+++ b/tests/tools/test_url_safety.py
@@ -454,6 +454,46 @@ class TestIPv4MappedIPv6SSRF:
             assert is_safe_url(url) is False
 
 
+class TestIPv4TranslatedIPv6SSRF:
+    """IPv4 answers can arrive wrapped as ``::ffff:0:x.x.x.x`` (RFC 2765 IPv4-translated — on the
+    reporting macOS host, fake-IP TUN DNS returns it alongside the plain address).
+    ``IPv6Address.ipv4_mapped`` is None for that form, so declaration coverage, the connect-time
+    check and the metadata floor must all classify it by the IPv4 it wraps."""
+
+    @pytest.fixture
+    def declared(self, monkeypatch):
+        monkeypatch.setattr(
+            "hermes_cli.config.read_raw_config",
+            lambda: {"security": {"fake_ip_ranges": ["198.18.0.0/15"]}},
+        )
+        _reset_allow_private_cache()
+        yield
+        _reset_allow_private_cache()
+
+    def test_declared_sentinel_block_covers_the_translated_wrapper(self, declared):
+        # ::ffff:0:c612:58 wraps 198.18.0.88 — inside the declared block.
+        with _resolves_to("::ffff:0:c612:58"):
+            assert is_safe_url("https://example.com/") is True
+        with _resolves_to("::ffff:0:c612:58"):
+            assert _resolved_http_connect_ips("example.com", 443, "https") == ["::ffff:0:c612:58"]
+
+    def test_translated_metadata_wrapper_still_hits_the_floor(self, monkeypatch):
+        # ::ffff:0:a9fe:a9fe wraps 169.254.169.254; the floor ignores allow_private_urls.
+        _reset_allow_private_cache()
+        with _resolves_to("::ffff:0:a9fe:a9fe"):
+            assert is_always_blocked_url("http://evil.example/") is True
+        monkeypatch.setenv("HERMES_ALLOW_PRIVATE_URLS", "true")
+        _reset_allow_private_cache()
+        with _resolves_to("::ffff:0:a9fe:a9fe"):
+            assert is_safe_url("http://evil.example/") is False
+        _reset_allow_private_cache()
+
+    def test_literal_translated_wrapper_hits_the_floor_without_dns(self):
+        # Attacker input need not come through DNS: the URL can carry the wrapper itself.
+        with patch("socket.getaddrinfo", side_effect=socket.gaierror("nope")):
+            assert is_always_blocked_url("http://[::ffff:0:a9fe:a9fe]/") is True
+
+
 class _FakeResponse:
     """Minimal stand-in for an httpx response as seen inside a response hook."""
 
diff --git a/tools/url_safety.py b/tools/url_safety.py
index e4972fada7..3ecb01123f 100644
--- a/tools/url_safety.py
+++ b/tools/url_safety.py
@@ -121,6 +121,11 @@ _MAX_SSRF_CONNECT_IPS = 8
 # ipaddress — must be blocked explicitly (Tailscale/WireGuard, cloud internal nets).
 _CGNAT_NETWORK = ipaddress.ip_network("100.64.0.0/10")
 
+# RFC 2765 IPv4-translated wrapper ``::ffff:0:a.b.c.d`` — the second form resolvers may use to
+# answer an IPv4 name (on the reporting macOS host, fake-IP TUN DNS returns it alongside the
+# plain address). ``ip.ipv4_mapped`` does not read it; ``_embedded_ipv4`` handles it explicitly.
+_IPV4_TRANSLATED_NETWORK = ipaddress.ip_network("::ffff:0:0:0/96")
+
 # Address classes a ``security.fake_ip_ranges`` declaration can never excuse: a local proxy owns
 # none of them, and a declaration is trusted like ``allow_private_urls`` for whatever it names,
 # so an entry overlapping one of these (including 0.0.0.0/0 and ::/0) would make real internal
@@ -242,7 +247,21 @@ def _getaddrinfo(hostname: str, port: Optional[int] = None):
     return socket.getaddrinfo(hostname, port, socket.AF_UNSPEC, socket.SOCK_STREAM)
 
 
+def _embedded_ipv4(ip: _IPAddress) -> _IPAddress:
+    """The IPv4 address an IPv6 wrapper stands for — IPv4-mapped (``::ffff:x.x.x.x``) or
+    IPv4-translated (``::ffff:0:x.x.x.x``); *ip* unchanged otherwise. ``ipaddress`` reads both
+    wrappers as distinct IPv6 addresses, so every classification must see through them, or a
+    resolver's sentinel / a cloud-metadata answer arrives as unrelated IPv6 space."""
+    if isinstance(ip, ipaddress.IPv6Address):
+        if ip.ipv4_mapped is not None:
+            return ip.ipv4_mapped
+        if ip in _IPV4_TRANSLATED_NETWORK:
+            return ipaddress.IPv4Address(int(ip) & 0xFFFFFFFF)
+    return ip
+
+
 def _is_always_blocked_ip(ip: _IPAddress) -> bool:
+    ip = _embedded_ipv4(ip)
     return ip in _ALWAYS_BLOCKED_IPS or any(ip in net for net in _ALWAYS_BLOCKED_NETWORKS)
 
 
@@ -250,16 +269,15 @@ def _is_declared_fake_ip(ip: _IPAddress) -> bool:
     """True when *ip* falls in a block declared in ``security.fake_ip_ranges``. The dial still goes
     to the local proxy, which resolves and connects to the real target, so a declared block grants
     no reach an attacker lacks through the proxy's own DNS; undeclared ranges keep the private verdict."""
-    if isinstance(ip, ipaddress.IPv6Address) and ip.ipv4_mapped is not None:
-        ip = ip.ipv4_mapped
+    ip = _embedded_ipv4(ip)
     return any(ip in net for net in _global_fake_ip_ranges())
 
 
 def _is_blocked_ip(ip: _IPAddress) -> bool:
     """Return True if the IP should be blocked for SSRF protection."""
-    # IPv4-mapped IPv6 (``::ffff:x.x.x.x``) is classified by its embedded IPv4.
-    if isinstance(ip, ipaddress.IPv6Address) and ip.ipv4_mapped is not None:
-        ip = ip.ipv4_mapped
+    # IPv4-wrapped IPv6 (mapped ``::ffff:x.x.x.x`` or translated ``::ffff:0:x.x.x.x``) is
+    # classified by its embedded IPv4.
+    ip = _embedded_ipv4(ip)
     return (ip.is_private or ip.is_loopback or ip.is_link_local or ip.is_reserved
             or ip.is_multicast or ip.is_unspecified or ip in _CGNAT_NETWORK)