diff --git a/Lib/test/test_monitoring.py b/Lib/test/test_monitoring.py
index d091572b0880d6..8c9755d2a41a2d 100644
--- a/Lib/test/test_monitoring.py
+++ b/Lib/test/test_monitoring.py
@@ -501,6 +501,22 @@ def test_two_with_disable(self):
             self.assertEqual(sys.monitoring._all_events(), {})
             sys.monitoring.restart_events()
 
+    def test_with_instruction_event(self):
+        """Test that the second tool can set events with instruction events set by the first tool."""
+        def f():
+            pass
+        code = f.__code__
+
+        try:
+            self.assertEqual(sys.monitoring._all_events(), {})
+            sys.monitoring.set_local_events(TEST_TOOL, code, E.INSTRUCTION | E.LINE)
+            sys.monitoring.set_local_events(TEST_TOOL2, code, E.LINE)
+        finally:
+            sys.monitoring.set_events(TEST_TOOL, 0)
+            sys.monitoring.set_events(TEST_TOOL2, 0)
+            self.assertEqual(sys.monitoring._all_events(), {})
+
+
 class LineMonitoringTest(MonitoringTestBase, unittest.TestCase):
 
     def test_lines_single(self):
diff --git a/Lib/test/test_sys_setprofile.py b/Lib/test/test_sys_setprofile.py
index 49e076c77d167a..34c70d6c8de0c4 100644
--- a/Lib/test/test_sys_setprofile.py
+++ b/Lib/test/test_sys_setprofile.py
@@ -439,7 +439,6 @@ def __del__(self):
         sys.setprofile(foo)
         self.assertEqual(sys.getprofile(), bar)
 
-
     def test_same_object(self):
         def foo(*args):
             ...
@@ -448,6 +447,18 @@ def foo(*args):
         del foo
         sys.setprofile(sys.getprofile())
 
+    def test_profile_after_trace_opcodes(self):
+        def f():
+            ...
+
+        sys._getframe().f_trace_opcodes = True
+        prev_trace = sys.gettrace()
+        sys.settrace(lambda *args: None)
+        f()
+        sys.settrace(prev_trace)
+        sys.setprofile(lambda *args: None)
+        f()
+
 
 if __name__ == "__main__":
     unittest.main()
diff --git a/Misc/NEWS.d/next/Core and Builtins/2023-09-13-21-04-04.gh-issue-109371.HPEJr8.rst b/Misc/NEWS.d/next/Core and Builtins/2023-09-13-21-04-04.gh-issue-109371.HPEJr8.rst
new file mode 100644
index 00000000000000..2fb18d5ae88347
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2023-09-13-21-04-04.gh-issue-109371.HPEJr8.rst	
@@ -0,0 +1 @@
+Deopted instructions correctly for tool initialization and modified the incorrect assertion in instrumentation, when a previous tool already sets INSTRUCTION events
diff --git a/Python/instrumentation.c b/Python/instrumentation.c
index 0a54eb67c31967..a6ff7a8a98506c 100644
--- a/Python/instrumentation.c
+++ b/Python/instrumentation.c
@@ -647,7 +647,7 @@ instrument(PyCodeObject *code, int i)
     if (opcode == INSTRUMENTED_INSTRUCTION) {
         opcode_ptr = &code->_co_monitoring->per_instruction_opcodes[i];
         opcode = *opcode_ptr;
-        CHECK(!is_instrumented(opcode));
+        CHECK(opcode != INSTRUMENTED_INSTRUCTION && opcode != INSTRUMENTED_LINE);
         CHECK(opcode == _PyOpcode_Deopt[opcode]);
     }
     CHECK(opcode != 0);
@@ -1252,6 +1252,9 @@ initialize_tools(PyCodeObject *code)
         if (opcode == INSTRUMENTED_LINE) {
             opcode = code->_co_monitoring->lines[i].original_opcode;
         }
+        if (opcode == INSTRUMENTED_INSTRUCTION) {
+            opcode = code->_co_monitoring->per_instruction_opcodes[i];
+        }
         bool instrumented = is_instrumented(opcode);
         if (instrumented) {
             opcode = DE_INSTRUMENT[opcode];