diff --git a/torch/_dynamo/output_graph.py b/torch/_dynamo/output_graph.py
index 4172e1cb980..78723c975e3 100644
--- a/torch/_dynamo/output_graph.py
+++ b/torch/_dynamo/output_graph.py
@@ -67,7 +67,7 @@ from torch.multiprocessing.reductions import StorageWeakRef
 from torch.utils._ordered_set import OrderedSet
 from torch.utils._python_dispatch import is_traceable_wrapper_subclass
 
-from . import config, exc, logging as torchdynamo_logging, variables
+from . import config, exc, graph_break_hints, logging as torchdynamo_logging, variables
 from .backends.registry import CompiledFn, CompilerFn
 from .bytecode_transformation import (
     create_call_function,
@@ -1253,6 +1253,18 @@ class OutputGraph(OutputGraphGuardsState):
 
         log.debug("COMPILING GRAPH due to %s", reason)
 
+        if not all(block.can_restore() for block in tx.block_stack):
+            unimplemented_v2(
+                gb_type="Attempt to compile graph with unrecoverable block in the block stack",
+                context="",
+                explanation="Dynamo does not support graph breaking on context managers in "
+                "nested function calls. For Python <= 3.10, this graph break may have instead been "
+                "caused by attempting to graph break in a try block.",
+                hints=[
+                    *graph_break_hints.CAUSED_BY_EARLIER_GRAPH_BREAK,
+                ],
+            )
+
         # prefix instructions (Python 3.11+)
         prefix_insts: list[Instruction] = []
         if sys.version_info >= (3, 11):
@@ -1295,8 +1307,6 @@ class OutputGraph(OutputGraphGuardsState):
         cur_tx: Optional[InstructionTranslatorBase] = tx
         while True:
             assert cur_tx is not None
-            # this should have been checked by the caller
-            assert all(block.can_restore() for block in cur_tx.block_stack)
             stack_values, restore_vars, meta = self._get_stack_values_to_restore(
                 cur_tx, stack_pops
             )