diff --git a/tests/tools/test_mcp_tool_session_expired.py b/tests/tools/test_mcp_tool_session_expired.py
index 7dba0505528b..6957c3ce6a8a 100644
--- a/tests/tools/test_mcp_tool_session_expired.py
+++ b/tests/tools/test_mcp_tool_session_expired.py
@@ -178,6 +178,83 @@ def test_is_session_expired_rejects_empty_message():
     assert _is_session_expired_error(Exception()) is False
 
 
+def test_is_session_expired_follows_cause_chain():
+    """A transport close reachable only via ``__cause__`` must classify."""
+    from anyio import ClosedResourceError
+    from tools.mcp_tool import _is_session_expired_error
+
+    try:
+        try:
+            raise ClosedResourceError()
+        except ClosedResourceError as inner:
+            raise RuntimeError("MCP request failed") from inner
+    except RuntimeError as exc:
+        assert _is_session_expired_error(exc) is True
+
+
+def test_is_session_expired_follows_context_chain():
+    """Implicit ``__context__`` chaining must also be scanned."""
+    from anyio import BrokenResourceError
+    from tools.mcp_tool import _is_session_expired_error
+
+    try:
+        try:
+            raise BrokenResourceError()
+        except BrokenResourceError:
+            raise RuntimeError("while handling transport write")
+    except RuntimeError as exc:
+        assert _is_session_expired_error(exc) is True
+
+
+def test_is_session_expired_interruption_in_cause_chain_wins():
+    """User cancellation buried in the chain overrides transport signals."""
+    from anyio import ClosedResourceError
+    from tools.mcp_tool import _is_session_expired_error
+
+    root = InterruptedError("cancel")
+    mid = ClosedResourceError()
+    mid.__cause__ = root
+    top = RuntimeError("transport is closed")
+    top.__cause__ = mid
+    assert _is_session_expired_error(top) is False
+
+
+def test_is_session_expired_handles_cyclic_cause_context_chain():
+    """Cycles through __cause__/__context__ must terminate (visited set)."""
+    from tools.mcp_tool import _is_session_expired_error
+
+    a = RuntimeError("a")
+    b = RuntimeError("b")
+    a.__cause__ = b
+    b.__context__ = a  # cycle back through the other link
+    assert _is_session_expired_error(a) is False
+
+    from anyio import ClosedResourceError
+
+    c = RuntimeError("c")
+    d = ClosedResourceError()
+    c.__cause__ = d
+    d.__context__ = c  # cycle, but transport error is reachable
+    assert _is_session_expired_error(c) is True
+
+
+def test_is_session_expired_traversal_is_budget_bounded():
+    """Pathologically long chains stop at the node budget without spinning."""
+    import tools.mcp_tool as mcp_mod
+    from tools.mcp_tool import _is_session_expired_error
+
+    exc: BaseException = RuntimeError("leaf")
+    for i in range(mcp_mod._EXC_TRAVERSAL_MAX_NODES * 2):
+        wrapper = RuntimeError(f"layer {i}")
+        wrapper.__cause__ = exc
+        exc = wrapper
+
+    # Terminates quickly and classifies false (no transport signal within
+    # budget). The exact outcome past the budget is unspecified; the
+    # invariant under test is termination.
+    assert _is_session_expired_error(exc) is False
+
+
 # ---------------------------------------------------------------------------
 # Handler integration — verify the recovery plumbing wires end-to-end
 # ---------------------------------------------------------------------------
diff --git a/tools/mcp_tool.py b/tools/mcp_tool.py
index ef8ed39145cb..a4303bdab5c8 100644
--- a/tools/mcp_tool.py
+++ b/tools/mcp_tool.py
@@ -3899,6 +3899,15 @@ _SESSION_EXPIRED_MARKERS: tuple = (
     "end of file",
 )
 
+# Upper bound on exception-graph nodes inspected by
+# ``_is_session_expired_error``. The visited-identity set already breaks
+# cycles across ``exceptions`` / ``__cause__`` / ``__context__``; the
+# budget additionally bounds pathological acyclic graphs (e.g. deeply
+# chained retries) so classification always terminates promptly. Kept
+# comfortably above ``sys.getrecursionlimit()`` so legitimately deep
+# wrapper stacks (task-group nesting) are still fully scanned.
+_EXC_TRAVERSAL_MAX_NODES = 10_000
+
 
 def _is_session_expired_error(exc: BaseException) -> bool:
     """Return True if ``exc`` looks like an MCP transport session expiry.
@@ -3929,18 +3938,29 @@ def _is_session_expired_error(exc: BaseException) -> bool:
         transport_error_types = ()
 
     # ExceptionGroup trees can be arbitrarily deep or even cyclic when custom
-    # exceptions expose ``exceptions``. Traverse once, iteratively, and inspect
-    # every reachable node so user interruption always overrides transport
-    # markers or types found elsewhere in the graph.
-    stack = [exc]
+    # exceptions expose ``exceptions``, and chained exceptions
+    # (``raise X from Y`` / implicit ``__context__``) can likewise form
+    # cycles when handlers re-raise previously seen exceptions. Traverse
+    # once, iteratively, with an identity-visited set AND a bounded node
+    # budget so classification can never spin, and inspect every reachable
+    # node so user interruption always overrides transport markers or types
+    # found elsewhere in the graph. The chain traversal matters for real
+    # failures: SDK wrappers often raise a generic RuntimeError *from* the
+    # message-less ClosedResourceError, leaving the transport signal only
+    # reachable via ``__cause__``.
+    stack: "list[BaseException | None]" = [exc]
     seen: set[int] = set()
     transport_error_found = False
-    while stack:
+    budget = _EXC_TRAVERSAL_MAX_NODES
+    while stack and budget > 0:
         current = stack.pop()
+        if current is None:
+            continue
         identity = id(current)
         if identity in seen:
             continue
         seen.add(identity)
+        budget -= 1
 
         if isinstance(current, InterruptedError):
             return False
@@ -3956,6 +3976,8 @@ def _is_session_expired_error(exc: BaseException) -> bool:
             transport_error_found = True
 
         stack.extend(getattr(current, "exceptions", ()))
+        stack.append(getattr(current, "__cause__", None))
+        stack.append(getattr(current, "__context__", None))
 
     return transport_error_found