RustPython
diff --git a/‎crates/vm/src/frame.rs‎
Lines changed: 30 additions & 13 deletions b/‎crates/vm/src/frame.rs‎
Lines changed: 30 additions & 13 deletions
@@ -815,22 +815,33 @@ impl ExecutingFrame<'_> {
             exception.set_traceback_typed(Some(new_traceback.into_ref(&vm.ctx)));
         }
 
-        // Fire PY_THROW event before raising the exception in the generator
-        {
+        // Fire PY_THROW and RAISE events before raising the exception in the
+        // generator.  do_monitor_exc in CPython replaces the active exception
+        // when a callback fails, so we mirror that here.
+        let exception = {
             use crate::stdlib::sys::monitoring;
             let monitoring_mask = vm.state.monitoring_events.load();
-            if monitoring_mask & monitoring::EVENT_PY_THROW != 0 {
+            let exception = if monitoring_mask & monitoring::EVENT_PY_THROW != 0 {
                 let offset = idx as u32 * 2;
                 let exc_obj: PyObjectRef = exception.clone().into();
-                let _ = monitoring::fire_py_throw(vm, self.code, offset, &exc_obj);
-            }
-            // Fire RAISE: the thrown exception is raised in this frame
+                match monitoring::fire_py_throw(vm, self.code, offset, &exc_obj) {
+                    Ok(()) => exception,
+                    Err(monitor_exc) => monitor_exc,
+                }
+            } else {
+                exception
+            };
             if monitoring_mask & monitoring::EVENT_RAISE != 0 {
                 let offset = idx as u32 * 2;
                 let exc_obj: PyObjectRef = exception.clone().into();
-                let _ = monitoring::fire_raise(vm, self.code, offset, &exc_obj);
+                match monitoring::fire_raise(vm, self.code, offset, &exc_obj) {
+                    Ok(()) => exception,
+                    Err(monitor_exc) => monitor_exc,
+                }
+            } else {
+                exception
             }
-        }
+        };
 
         // when raising an exception, set __context__ to the current exception
         // This is done in _PyErr_SetObject
@@ -844,17 +855,23 @@ impl ExecutingFrame<'_> {
             Ok(None) => self.run(vm),
             Ok(Some(result)) => Ok(result),
             Err(exception) => {
-                // Fire PY_UNWIND: exception escapes the generator frame
-                if vm.state.monitoring_events.load()
+                // Fire PY_UNWIND: exception escapes the generator frame.
+                // do_monitor_exc replaces the exception on callback failure.
+                let exception = if vm.state.monitoring_events.load()
                     & crate::stdlib::sys::monitoring::EVENT_PY_UNWIND
                     != 0
                 {
                     let offset = idx as u32 * 2;
                     let exc_obj: PyObjectRef = exception.clone().into();
-                    let _ = crate::stdlib::sys::monitoring::fire_py_unwind(
+                    match crate::stdlib::sys::monitoring::fire_py_unwind(
                         vm, self.code, offset, &exc_obj,
-                    );
-                }
+                    ) {
+                        Ok(()) => exception,
+                        Err(monitor_exc) => monitor_exc,
+                    }
+                } else {
+                    exception
+                };
                 Err(exception)
             }
         }