Rough initial prototype:

diff --git a/datasette/views/table.py b/datasette/views/table.py
index 8b987221..518ac578 100644
--- a/datasette/views/table.py
+++ b/datasette/views/table.py
@@ -1103,19 +1103,30 @@ class TableInsertView(BaseView):
         except json.JSONDecodeError as e:
             return _errors(["Invalid JSON: {}".format(e)])
         if not isinstance(data, dict):
-            return _errors(["JSON must be a dictionary"])
+            return _errors([{"detail": "JSON must be a dictionary", "pointer": "#/"}])
         keys = data.keys()
 
         # keys must contain "row" or "rows"
         if "row" not in keys and "rows" not in keys:
             return _errors(['JSON must have one or other of "row" or "rows"'])
         rows = []
+        was_single_row = False
         if "row" in keys:
             if "rows" in keys:
-                return _errors(['Cannot use "row" and "rows" at the same time'])
+                return _errors(
+                    [
+                        {
+                            "detail": 'Cannot use "row" and "rows" at the same time',
+                            "pointer": "#/row",
+                        }
+                    ]
+                )
+            was_single_row = True
             row = data["row"]
             if not isinstance(row, dict):
-                return _errors(['"row" must be a dictionary'])
+                return _errors(
+                    [{"detail": '"row" must be a dictionary', "pointer": "#/row"}]
+                )
             rows = [row]
             data["return"] = True
         else:
@@ -1152,9 +1163,12 @@ class TableInsertView(BaseView):
             invalid_columns = set(row.keys()) - columns
             if invalid_columns:
                 errors.append(
-                    "Row {} has invalid columns: {}".format(
-                        i, ", ".join(sorted(invalid_columns))
-                    )
+                    {
+                        "detail": "Invalid columns: {}".format(
+                            ", ".join(sorted(invalid_columns))
+                        ),
+                        "pointer": "#/blah/",
+                    }
                 )
         if errors:
             return _errors(errors)

Uh oh!

Figure out design for JSON errors (consider RFC 7807) #1875

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