I've searched around on Google before posting this and didn't found
anything useful. So, feel free to point me to a URL that answers this
is you find one.

I have a Category class. Categories have Datapoints and Categories. I
want to JSON-ify this deeply nested tree structure, but it fails at
the second level.

Does anyone know how to configure the json_serializer so that it
traverses past the first depth of associations?

I configured it like this: Category.plugin :json_serializer, :include
=> {:categories => {:include => Category.columns +
[:datapoints]}, :datapoints => {:include => Datapoint.columns}}

Here's a simple example of one category (classcat_id => 1010138) that
has a subcategory (classcat_id => 1010140). That subcategory has a
single datapoint:

[
  {
    "json_class": "Category",
    "class_id": 10010,
    "class_parent": null,
    "class_name": "Manual Test Cases",
    "class_tag": "JWH_TEST_CASE",
    "classcat_id": 1010138,
    "classcat_parent": null,
    "classcat_class": 10010,
    "classcat_name": "Imported Data",
    "categories": [
      {
        "json_class": "Category",
        "class_id": 10010,
        "class_parent": null,
        "class_name": "Manual Test Cases",
        "class_tag": "JWH_TEST_CASE",
        "class_description": null,
        "class_keywords": null,
        "class_can_publish": 1,
        "class_is_active": 1,
        "classcat_id": 1010140,
        "classcat_parent": 1010138,
        "classcat_class": 10010,
        "classcat_tag": "TEST_IMPORT_CIRC_OUTPUT",
        "datapoints": [
          "#<Datapoint:0x6e5cbebb>"
        ]
      }
    ],
    "datapoints": [ ]
  }
]

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