diff --git a/src/debugpy/_vendored/pydevd/_pydevd_bundle/pydevd_comm.py b/src/debugpy/_vendored/pydevd/_pydevd_bundle/pydevd_comm.py
index 97ec9556d..c223e3445 100644
--- a/src/debugpy/_vendored/pydevd/_pydevd_bundle/pydevd_comm.py
+++ b/src/debugpy/_vendored/pydevd/_pydevd_bundle/pydevd_comm.py
@@ -72,7 +72,8 @@
 from _pydev_bundle._pydev_saved_modules import socket as socket_module
 from _pydevd_bundle.pydevd_constants import (DebugInfoHolder, IS_WINDOWS, IS_JYTHON,
     IS_PY36_OR_GREATER, STATE_RUN, ASYNC_EVAL_TIMEOUT_SEC,
-    get_global_debugger, GetGlobalDebugger, set_global_debugger, silence_warnings_decorator)  # Keep for backward compatibility @UnusedImport
+    get_global_debugger, GetGlobalDebugger, set_global_debugger,  # Keep for backward compatibility @UnusedImport
+    silence_warnings_decorator, filter_all_warnings)
 from _pydev_bundle.pydev_override import overrides
 import weakref
 from _pydev_bundle._pydev_completer import extract_token_and_qualifier
@@ -1121,7 +1122,6 @@ def _evaluate_response(py_db, request, result, error_message=''):
 _global_frame = None
 
 
-@silence_warnings_decorator
 def internal_evaluate_expression_json(py_db, request, thread_id):
     '''
     :param EvaluateRequest request:
@@ -1137,13 +1137,15 @@ def internal_evaluate_expression_json(py_db, request, thread_id):
     if hasattr(fmt, 'to_dict'):
         fmt = fmt.to_dict()
 
-    if context == 'repl' and not py_db.is_output_redirected:
-        ctx = pydevd_io.redirect_stream_to_pydb_io_messages_context()
+    ctx = NULL
+    if context == 'repl':
+        if not py_db.is_output_redirected:
+            ctx = pydevd_io.redirect_stream_to_pydb_io_messages_context()
     else:
-        ctx = NULL
+        # If we're not in a repl (watch, hover, ...) don't show warnings.
+        ctx = filter_all_warnings()
 
     with ctx:
-
         try_exec = False
         if frame_id is None:
             if _global_frame is None:
diff --git a/src/debugpy/_vendored/pydevd/_pydevd_bundle/pydevd_constants.py b/src/debugpy/_vendored/pydevd/_pydevd_bundle/pydevd_constants.py
index a8d974c9e..07a7b2c39 100644
--- a/src/debugpy/_vendored/pydevd/_pydevd_bundle/pydevd_constants.py
+++ b/src/debugpy/_vendored/pydevd/_pydevd_bundle/pydevd_constants.py
@@ -7,6 +7,7 @@
 import struct
 import warnings
 import functools
+from contextlib import contextmanager
 
 STATE_RUN = 1
 STATE_SUSPEND = 2
@@ -443,12 +444,18 @@ def as_str(s):
     return s
 
 
+@contextmanager
+def filter_all_warnings():
+    with warnings.catch_warnings():
+        warnings.filterwarnings("ignore")
+        yield
+
+
 def silence_warnings_decorator(func):
 
     @functools.wraps(func)
     def new_func(*args, **kwargs):
-        with warnings.catch_warnings():
-            warnings.filterwarnings("ignore")
+        with filter_all_warnings():
             return func(*args, **kwargs)
 
     return new_func
diff --git a/src/debugpy/_vendored/pydevd/tests_python/test_debugger_json.py b/src/debugpy/_vendored/pydevd/tests_python/test_debugger_json.py
index 9ef5ea3cc..69f74c53d 100644
--- a/src/debugpy/_vendored/pydevd/tests_python/test_debugger_json.py
+++ b/src/debugpy/_vendored/pydevd/tests_python/test_debugger_json.py
@@ -1854,6 +1854,31 @@ def test_getattr_warning(case_setup):
         writer.finished_ok = True
 
 
+def test_warning_on_repl(case_setup):
+
+    def additional_output_checks(writer, stdout, stderr):
+        assert "WarningCalledOnRepl" in stderr
+
+    with case_setup.test_file(
+        '_debugger_case_evaluate.py',
+        additional_output_checks=additional_output_checks
+        ) as writer:
+        json_facade = JsonFacade(writer)
+
+        json_facade.write_set_breakpoints(writer.get_line_index_with_content('Break here'))
+        json_facade.write_make_initial_run()
+
+        json_hit = json_facade.wait_for_thread_stopped()
+
+        # We want warnings from the in evaluate in the repl (but not hover/watch).
+        json_facade.evaluate(
+            'import warnings; warnings.warn("WarningCalledOnRepl")', json_hit.frame_id, context='repl')
+
+        json_facade.write_continue()
+
+        writer.finished_ok = True
+
+
 def test_evaluate_numpy(case_setup, pyfile):
     try:
         import numpy