diff --git a/jedi/inference/gradual/annotation.py b/jedi/inference/gradual/annotation.py
index 81780010..57098276 100644
--- a/jedi/inference/gradual/annotation.py
+++ b/jedi/inference/gradual/annotation.py
@@ -402,6 +402,10 @@ def find_type_from_comment_hint_for(context, node, name):
 
 
 def find_type_from_comment_hint_with(context, node, name):
+    if len(node.children) > 4:
+        # In case there are multiple with_items, we do not want a type hint for
+        # now.
+        return []
     assert len(node.children[1].children) == 3, \
         "Can only be here when children[1] is 'foo() as f'"
     varlist = node.children[1].children[2]
diff --git a/test/completion/basic.py b/test/completion/basic.py
index 97bfeecd..53df851e 100644
--- a/test/completion/basic.py
+++ b/test/completion/basic.py
@@ -413,6 +413,10 @@ with Foo() as f3:
 with Foo() as f3:
     f3
 
+with open("a"), open("b") as bfile:
+    #? ['flush']
+   bfile.flush
+
 # -----------------
 # Avoiding multiple definitions
 # -----------------