diff --git a/src/object/base.rs b/src/object/base.rs
index 9ad81b451..ea86386c6 100644
--- a/src/object/base.rs
+++ b/src/object/base.rs
@@ -354,7 +354,16 @@ impl Value {
 
         if let Value::Object(ref mut o) = new_obj {
             let mut current = o;
-            for idx in 0..split_path.len() - 1 {
+
+            if split_path.len() == 1 {
+                // Special case for inserting at the top level
+                current
+                    .entries
+                    .insert(path.to_string(), Tagged::from_item(new_value, tag));
+                return Some(Tagged::from_item(new_obj, tag));
+            }
+
+            for idx in 0..split_path.len() {
                 match current.entries.get_mut(split_path[idx]) {
                     Some(next) => {
                         if idx == (split_path.len() - 2) {
diff --git a/src/plugins/add.rs b/src/plugins/add.rs
index 11b90de63..2634c1497 100644
--- a/src/plugins/add.rs
+++ b/src/plugins/add.rs
@@ -23,9 +23,10 @@ impl Add {
                 Some(f) => match obj.insert_data_at_path(value_tag, &f, v) {
                     Some(v) => return Ok(v),
                     None => {
-                        return Err(ShellError::string(
-                            "add could not find place to insert field",
-                        ))
+                        return Err(ShellError::string(format!(
+                            "add could not find place to insert field {:?} {}",
+                            obj, f
+                        )))
                     }
                 },
                 None => Err(ShellError::string(