diff --git a/src/debugpy/common/json.py b/src/debugpy/common/json.py
index d5bd12daa..6f3e2b214 100644
--- a/src/debugpy/common/json.py
+++ b/src/debugpy/common/json.py
@@ -7,6 +7,7 @@
 
 import builtins
 import json
+import numbers
 import operator
 
 
@@ -92,6 +93,16 @@ def __format__(self, format_spec):
 # some substitutions - e.g. replacing () with some default value.
 
 
+def _converter(value, classinfo):
+    """Convert value (str) to number, otherwise return None if is not possible"""
+    for one_info in classinfo:
+        if issubclass(one_info, numbers.Number):
+            try:
+                return one_info(value)
+            except ValueError:
+                pass
+
+
 def of_type(*classinfo, **kwargs):
     """Returns a validator for a JSON property that requires it to have a value of
     the specified type. If optional=True, () is also allowed.
@@ -107,6 +118,10 @@ def validate(value):
         if (optional and value == ()) or isinstance(value, classinfo):
             return value
         else:
+            converted_value = _converter(value, classinfo)
+            if converted_value:
+                return converted_value
+
             if not optional and value == ():
                 raise ValueError("must be specified")
             raise TypeError("must be " + " or ".join(t.__name__ for t in classinfo))
diff --git a/tests/debugpy/common/test_messaging.py b/tests/debugpy/common/test_messaging.py
index 7ba88e886..335a5ead8 100644
--- a/tests/debugpy/common/test_messaging.py
+++ b/tests/debugpy/common/test_messaging.py
@@ -656,3 +656,21 @@ def _send_requests_and_events(self, channel):
         assert fuzzer2.sent == fuzzer1.received
         assert fuzzer1.responses_sent == fuzzer2.responses_received
         assert fuzzer2.responses_sent == fuzzer1.responses_received
+
+
+class TestTypeConversion(object):
+    def test_str_to_num(self):
+
+        # test conversion that are expected to work
+        correct_trials = [("1.0", float), ("1", int), ("1", bool)]
+        for val_trial, type_trial in correct_trials:
+            assert isinstance(
+                json.of_type(type_trial)(val_trial), type_trial
+            ), "Wrong type coversion"
+
+        # test conversion that are not expected to work
+        try:
+            json.of_type(int)("1.0")
+            raise ValueError("This test should have failed")
+        except TypeError:
+            pass