diff --git a/sphinx/ext/autosummary/__init__.py b/sphinx/ext/autosummary/__init__.py
index 379fd48ad0..8810a5088f 100644
--- a/sphinx/ext/autosummary/__init__.py
+++ b/sphinx/ext/autosummary/__init__.py
@@ -614,9 +614,11 @@ def get_import_prefixes_from_env(env: BuildEnvironment) -> List[str]:
     return prefixes
 
 
-def import_by_name(name: str, prefixes: List[str] = [None]) -> Tuple[str, Any, Any, str]:
+def import_by_name(name: str, prefixes: List[str] = [None], last_errors = None) -> Tuple[str, Any, Any, str]:
     """Import a Python object that has the given *name*, under one of the
     *prefixes*.  The first name that succeeds is used.
+    If importing fails, *last_errors* will contain the exceptions raised during
+    import and may help to identify the problem.
     """
     tried = []
     for prefix in prefixes:
@@ -625,14 +627,14 @@ def import_by_name(name: str, prefixes: List[str] = [None]) -> Tuple[str, Any, A
                 prefixed_name = '.'.join([prefix, name])
             else:
                 prefixed_name = name
-            obj, parent, modname = _import_by_name(prefixed_name)
+            obj, parent, modname = _import_by_name(prefixed_name, last_errors)
             return prefixed_name, obj, parent, modname
         except ImportError:
             tried.append(prefixed_name)
     raise ImportError('no module named %s' % ' or '.join(tried))
 
 
-def _import_by_name(name: str) -> Tuple[Any, Any, str]:
+def _import_by_name(name: str, last_errors = None) -> Tuple[Any, Any, str]:
     """Import a Python object given its full name."""
     try:
         name_parts = name.split('.')
@@ -643,8 +645,9 @@ def _import_by_name(name: str) -> Tuple[Any, Any, str]:
             try:
                 mod = import_module(modname)
                 return getattr(mod, name_parts[-1]), mod, modname
-            except (ImportError, IndexError, AttributeError):
-                pass
+            except (ImportError, IndexError, AttributeError) as e:
+                if last_errors is not None:
+                    last_errors.append(e)
 
         # ... then as MODNAME, MODNAME.OBJ1, MODNAME.OBJ1.OBJ2, ...
         last_j = 0
@@ -654,7 +657,9 @@ def _import_by_name(name: str) -> Tuple[Any, Any, str]:
             modname = '.'.join(name_parts[:j])
             try:
                 import_module(modname)
-            except ImportError:
+            except ImportError as e:
+                if last_errors is not None:
+                    last_errors.append(e)
                 continue
 
             if modname in sys.modules:
@@ -673,7 +678,7 @@ def _import_by_name(name: str) -> Tuple[Any, Any, str]:
         raise ImportError(*e.args) from e
 
 
-def import_ivar_by_name(name: str, prefixes: List[str] = [None]) -> Tuple[str, Any, Any, str]:
+def import_ivar_by_name(name: str, prefixes: List[str] = [None], last_errors = None) -> Tuple[str, Any, Any, str]:
     """Import an instance variable that has the given *name*, under one of the
     *prefixes*.  The first name that succeeds is used.
     """
@@ -686,8 +691,9 @@ def import_ivar_by_name(name: str, prefixes: List[str] = [None]) -> Tuple[str, A
         # check for presence in `annotations` to include dataclass attributes
         if (qualname, attr) in analyzer.attr_docs or (qualname, attr) in analyzer.annotations:
             return real_name + "." + attr, INSTANCEATTR, obj, modname
-    except (ImportError, ValueError, PycodeError):
-        pass
+    except (ImportError, ValueError, PycodeError) as e:
+        if last_errors is not None:
+            last_errors.append(e)
 
     raise ImportError
 
diff --git a/sphinx/ext/autosummary/generate.py b/sphinx/ext/autosummary/generate.py
index 4f3493659d..dcbebd341d 100644
--- a/sphinx/ext/autosummary/generate.py
+++ b/sphinx/ext/autosummary/generate.py
@@ -413,16 +413,21 @@ def generate_autosummary_docs(sources: List[str], output_dir: str = None,
         path = output_dir or os.path.abspath(entry.path)
         ensuredir(path)
 
+        last_errors = []
+
         try:
-            name, obj, parent, modname = import_by_name(entry.name)
+            name, obj, parent, modname = import_by_name(entry.name, last_errors=last_errors)
             qualname = name.replace(modname + ".", "")
         except ImportError as e:
             try:
-                # try to importl as an instance attribute
-                name, obj, parent, modname = import_ivar_by_name(entry.name)
+                # try to import as an instance attribute
+                name, obj, parent, modname = import_ivar_by_name(entry.name, last_errors=last_errors)
                 qualname = name.replace(modname + ".", "")
             except ImportError:
-                logger.warning(__('[autosummary] failed to import %r: %s') % (entry.name, e))
+                # Convert exceptions to strings and remove duplicates (convert to set, then to list)
+                last_errors_str = list(set(str(e) for e in last_errors))
+                logger.warning(__('[autosummary] failed to import %r: %s. Possible hints: %s') %
+                               (entry.name, e, last_errors_str))
                 continue
 
         context: Dict[str, Any] = {}