We recently ran into a weird JSON-related issue in Ruby, namely that to_json and JSON.parse are not symmetric.

irb(main):004:0> JSON.parse("hello".to_json)
JSON::ParserError: 757: unexpected token at '"hello"'
	from /System/Library/Frameworks/Ruby.framework/Versions/2.0/usr/lib/ruby/2.0.0/json/common.rb:155:in `parse'
	from /System/Library/Frameworks/Ruby.framework/Versions/2.0/usr/lib/ruby/2.0.0/json/common.rb:155:in `parse'
	from (irb):4
	from /usr/bin/irb:12:in `'

It turns out that JSON.parse expects a valid JSON document, which is defined on json.org as follows:

JSON is built on two structures:

• A collection of name/value pairs. In various languages, this is realized as an object, record, struct, dictionary, hash table, keyed list, or associative array.
• An ordered list of values. In most languages, this is realized as an array, vector, list, or sequence.

So a single JSON value will never be a valid JSON document.  Toward this end, JSON.generate is actually the symmetric function you are looking for – it only accepts hashes and arrays.  to_json can be used to convert single values, but it is often not what you are looking for.

Should you find yourself in a situation where you need to eval messy JSON, you can enable quirks_mode on JSON.parse, which will behave closer to your expectations

JSON.parse("hello".to_json, :quirks_mode => true) # => "hello"