diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2025-12-16-20-38-17.gh-issue-142448.mAFqwL.rst b/Misc/NEWS.d/next/Core_and_Builtins/2025-12-16-20-38-17.gh-issue-142448.mAFqwL.rst
new file mode 100644
index 00000000000000..bcc7c1fb12d094
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2025-12-16-20-38-17.gh-issue-142448.mAFqwL.rst
@@ -0,0 +1 @@
+Fix a bug when using monitoring with the JIT.
diff --git a/Python/bytecodes.c b/Python/bytecodes.c
index 391fa8ea2a94ec..8cc6b9d6c98d69 100644
--- a/Python/bytecodes.c
+++ b/Python/bytecodes.c
@@ -5587,9 +5587,14 @@ dummy_func(
             next_instr = this_instr;
             frame->instr_ptr = prev_instr;
             opcode = next_instr->op.code;
-            bool stop_tracing = (opcode == WITH_EXCEPT_START ||
-                opcode == RERAISE || opcode == CLEANUP_THROW ||
-                opcode == PUSH_EXC_INFO || opcode == INTERPRETER_EXIT);
+            bool stop_tracing = (
+                opcode == WITH_EXCEPT_START ||
+                opcode == RERAISE ||
+                opcode == CLEANUP_THROW ||
+                opcode == PUSH_EXC_INFO ||
+                opcode == INTERPRETER_EXIT ||
+                (opcode >= MIN_INSTRUMENTED_OPCODE && opcode != ENTER_EXECUTOR)
+            );
             int full = !_PyJit_translate_single_bytecode_to_trace(tstate, frame, next_instr, stop_tracing ? _DEOPT : 0);
             if (full) {
                 LEAVE_TRACING();
diff --git a/Python/generated_cases.c.h b/Python/generated_cases.c.h
index 94846d718308a5..7f0db0ad4c1379 100644
--- a/Python/generated_cases.c.h
+++ b/Python/generated_cases.c.h
@@ -11574,9 +11574,14 @@
             next_instr = this_instr;
             frame->instr_ptr = prev_instr;
             opcode = next_instr->op.code;
-            bool stop_tracing = (opcode == WITH_EXCEPT_START ||
-                                 opcode == RERAISE || opcode == CLEANUP_THROW ||
-                                 opcode == PUSH_EXC_INFO || opcode == INTERPRETER_EXIT);
+            bool stop_tracing = (
+                                 opcode == WITH_EXCEPT_START ||
+                                 opcode == RERAISE ||
+                                 opcode == CLEANUP_THROW ||
+                                 opcode == PUSH_EXC_INFO ||
+                                 opcode == INTERPRETER_EXIT ||
+                                 (opcode >= MIN_INSTRUMENTED_OPCODE && opcode != ENTER_EXECUTOR)
+            );
             _PyFrame_SetStackPointer(frame, stack_pointer);
             int full = !_PyJit_translate_single_bytecode_to_trace(tstate, frame, next_instr, stop_tracing ? _DEOPT : 0);
             stack_pointer = _PyFrame_GetStackPointer(frame);