diff --git a/astroid/brain/brain_builtin_inference.py b/astroid/brain/brain_builtin_inference.py
index a56b1525c..9ab7b8b23 100644
--- a/astroid/brain/brain_builtin_inference.py
+++ b/astroid/brain/brain_builtin_inference.py
@@ -769,7 +769,9 @@ def infer_issubclass(callnode, context: InferenceContext | None = None):
     except (InferenceError, StopIteration) as exc:
         raise UseInferenceDefault from exc
     if not isinstance(obj_type, nodes.ClassDef):
-        raise UseInferenceDefault("TypeError: arg 1 must be class")
+        raise UseInferenceDefault(
+            f"TypeError: arg 1 must be class, not {type(obj_type)!r}"
+        )
 
     # The right hand argument is the class(es) that the given
     # object is to be checked against.
diff --git a/astroid/brain/brain_namedtuple_enum.py b/astroid/brain/brain_namedtuple_enum.py
index 104bd9764..2cbb17097 100644
--- a/astroid/brain/brain_namedtuple_enum.py
+++ b/astroid/brain/brain_namedtuple_enum.py
@@ -280,7 +280,9 @@ def _check_namedtuple_attributes(typename, attributes, rename=False):
     # <snippet>
     for name in (typename, *attributes):
         if not isinstance(name, str):
-            raise AstroidTypeError("Type names and field names must be strings")
+            raise AstroidTypeError(
+                f"Type names and field names must be strings, not {type(name)!r}"
+            )
         if not name.isidentifier():
             raise AstroidValueError(
                 "Type names and field names must be valid" + f"identifiers: {name!r}"
diff --git a/astroid/helpers.py b/astroid/helpers.py
index 62a72595e..360c1ae90 100644
--- a/astroid/helpers.py
+++ b/astroid/helpers.py
@@ -129,7 +129,9 @@ def _object_type_is_subclass(
     # issubclass(object, (1, type)) raises TypeError
     for klass in class_seq:
         if isinstance(klass, util.UninferableBase):
-            raise AstroidTypeError("arg 2 must be a type or tuple of types")
+            raise AstroidTypeError(
+                f"arg 2 must be a type or tuple of types, not {type(klass)!r}"
+            )
 
         for obj_subclass in obj_type.mro():
             if obj_subclass == klass:
@@ -164,7 +166,7 @@ def object_issubclass(
         or its type's mro doesn't work
     """
     if not isinstance(node, nodes.ClassDef):
-        raise TypeError(f"{node} needs to be a ClassDef node")
+        raise TypeError(f"{node} needs to be a ClassDef node, not {type(node)!r}")
     return _object_type_is_subclass(node, class_or_seq, context=context)
 
 
diff --git a/astroid/protocols.py b/astroid/protocols.py
index 7cc50810f..387f9f8ac 100644
--- a/astroid/protocols.py
+++ b/astroid/protocols.py
@@ -809,7 +809,7 @@ def _determine_starred_iteration_lookups(
 
         if not isinstance(target, nodes.Tuple):
             raise InferenceError(
-                "Could not make sense of this, the target must be a tuple",
+                f"Could not make sense of this, the target must be a tuple, not {type(target)!r}",
                 context=context,
             )