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7.6 JSON Does Not Round-Trip Cleanly to Python

A Python developer can be tempted into mistakenly thinking that arbitrary Python objects can be serialized as JSON, and relatedly that objects that can be serialized are necessarily deserialized as equivalent objects.

7.6.1 Some Background on JSON

In the modern world of microservices and “cloud-native computing,” Python often needs to serialize and deserialize JavaScript Object Notation ( JSON) data. Moreover, JSON doesn’t only occur in the context of message exchange between small cooperating services, but is also used as a storage representation of certain structured data. For example, GeoJSON and the related TopoJSON, or JSON-LD for ontology and knowledge graph data, are formats that utilize JSON to encode domain-specific structures.

In surface appearance, JSON looks very similar to Python numbers, strings, lists, and dictionaries. The similarity is sufficient that for many JSON strings, simply writing eval(json_str) will deserialize a string to a valid Python object; in fact, this will often (but certainly not always) produce the same result as the correct approach of json.loads(json_str). JSON looks even more similar to native expressions in JavaScript (as the name hints), but even there, a few valid JSON strings cannot be deserialized (meaningfully) into JavaScript.

While superficially json.loads() performs a similar task as pickle.loads(), and json.dumps() performs a similar task as pickle.dumps(), the JSON versions do distinctly less in numerous situations. The “type system” of JSON is less rich than is that of Python. For a large subset of all Python objects, including (deeply) nested data structures, this invariant holds:

obj == pickle.loads(pickle.dumps(obj))

There are exceptions here. File handles or open sockets cannot be sensibly serialized and deserialized, for example. But most data structures, including custom classes, survive this round-trip perfectly well.

In contrast, this “invariant” is very frequently violated:

obj = json.loads(json.dumps(obj))

JSON is a very useful format in several ways. It is (relatively) readable pure text; it is highly interoperable with services written in other programming languages with which a Python program would like to cooperate; deserializing JSON does not introduce code execution vulnerabilities.

Pickle (in its several protocol versions) is also useful. It is a binary serialization format that is more compact than text. Or specifically, it is protocol 0, 1, 2, 3, 4, or 5, with each successive version being improved in some respect, but all following that characterization. Almost all Python objects can be serialized in a round-trippable way using the pickle module. However, none of the services you might wish to interact with, written in JavaScript, Go, Rust, Kotlin, C++, Ruby, or other languages, has any idea what to do with Python pickles.

7.6.2 Data That Fails to Round-Trip

In the first place, JSON only defines a few datatypes. These are discussed in RFC 8256 (https://datatracker.ietf.org/doc/html/rfc8259), ECMA-404 (https://www.ecmainternational.org/publications-and-standards/standards/ecma-404/), and ISO/IEC 21778:2017 (https://www.iso.org/standard/71616.html). Despite having “the standard” enshrined by several standards bodies in not-quite-identical language, these standards are equivalent.

We should back up for a moment. I’ve now twice claimed—a bit incorrectly—that JSON has a limited number of datatypes. In reality, JSON has zero datatypes, and instead is, strictly speaking, only a definition of a syntax with no semantics whatsoever. As RFC 8256 defines the highest level of its BNF (Backus–Naur form):

value ::= false | null | true | object | array | number | string

Here false, null, and true are literals, while object, array, number, and string are textual patterns. To simplify, a JSON object is like a Python dictionary, with curly braces, colons, and commas. An array is like a Python list, with square brackets and commas. A number can take a number of formats, but the rules are almost the same as what defines valid Python numbers. Likewise, JSON strings are almost the same as the spelling of Python strings, but always with double quotation marks. Unicode numeric codes are mostly the same between JSON and Python (edge cases concern very obscure surrogate pair handling).

Let’s take a look at some edge cases. The Python standard library module json “succeeds” in two cases by producing output that is not actually JSON:

>>> import json
>>> import math
>>> print(json.dumps({"nan": math.nan}))            # ❶
{"nan": NaN}
>>> print(json.dumps({"inf": math.inf}))
{"inf": Infinity}
>>> json.loads(json.dumps({'nan': math.nan}))       # ❷
{'nan': nan}
>>> json.loads(json.dumps({'inf': math.inf}))
{'inf': inf}

❶ The result of json.dumps() is a string; printing it just removes the extra quotes in the echoed representation.

❷ Neither NaN nor Infinity (under any spelling variation) are in the JSON standards.

In some sense, this behavior is convenient for Python programmers, but it breaks compatibility with (many) consumers of these serializations in other programming languages. We can enforce more strictness with json.dumps(obj, allow_nan=False), which would raise ValueError in the preceding lines. However, some other libraries in some other programming languages also allow this almost-JSON convention.

Depending on what you mean by “round-trip,” you might say this succeeded. Indeed it does strictly within Python itself; but it fails when the round-trip involves talking with a service written in a different programming language, and it talking back. Let’s look at some failures within Python itself. The most obvious cases are in Python’s more diverse collection types.

Not-quite round-tripping collections with JSON
>>> from collections import namedtuple
>>> Person = namedtuple("Person", "first last body_temp")
>>> david = Person("David", "Mertz", "37°C")
>>> vector1 = (4.6, 3.2, 1.5)
>>> vector2 = (9.8, -1.2, 0.4)
>>> obj = {1: david, 2: [vector1, vector2], 3: True, 4: None}
>>> obj
{1: Person(first='David', last='Mertz', body_temp='37°C'),
2: [(4.6, 3.2, 1.5), (9.8, -1.2, 0.4)], 3: True, 4: None}

>>> print(json.dumps(obj))
{"1": ["David", "Mertz", "37\u2103"], "2": [[4.6, 3.2, 1.5],
[9.8, -1.2, 0.4]], "3": true, "4": null}
>>> json.loads(json.dumps(obj))
{'1': ['David', 'Mertz', '37°C'], '2': [[4.6, 3.2, 1.5],
[9.8, -1.2, 0.4]], '3': True, '4': None}

In JSON, Python’s True is spelled true, and None is spelled null, but those are entirely literal spelling changes. Likewise, the Unicode character DEGREE CELSIUS can perfectly well live inside a JSON string (or any Unicode character other than a quotation mark, reverse solidus/backslash, and the control characters U+0000 through U+001F). For some reason, Python’s json module decided to substitute with the numeric code, but such has no effect on the round-trip.

What got lost was that some data was inside a namedtuple called Person, and other data was inside tuples. JSON only has arrays, that is, things in square brackets. The general “meaning” of the data is still there, but we’ve lost important type information.

Moreover, in the serialization, only strings are permitted as object keys, and hence our valid-in-Python integer keys were converted to strings. However, this is lossy since a Python dictionary could, in principle (but it’s not great code), have both string and numeric keys:

>>> json.dumps({1: "foo", "1": "bar"})
'{"1": "foo", "1": "bar"}'
>>> json.loads(json.dumps({1: "foo", "1": "bar"}))
{'1': 'bar'}

Two or three things conspired against us here. Firstly, the JSON specification doesn’t prevent duplicate keys from occurring. Secondly, the integer 1 is converted to the string "1" when it becomes JSON. And thirdly, Python dictionaries always have unique keys, so the second try at setting the "1" key overwrote the first try.

Another somewhat obscure edge case is that JSON itself can validly represent numbers that Python does not support:

>>> json_str = '[1E400, 3.141592653589793238462643383279]'
>>> json.loads(json_str)
[inf, 3.141592653589793]

This is not a case of crashing, nor failing to load numbers at all. But rather, one number overflows to infinity since it is too big for float64, and the other is approximated to fewer digits of precision than are provided.

A corner edge case is that JSON numbers that “look like Python integers” actually get cast to int rather than float:

>>> json_str = f'{"7"*400}'                         # ❶
>>> val = json.loads(json_str)
>>> math.log10(val)
399.8908555305749
>>> type(val)
<class 'int'>

❶ A string of four hundred "7"s in a row

However, since few other programming languages or architectures you might communicate with will support, for example, float128 either, the best policy is usually to stick with numbers float64 can represent.

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