This aspect is now well under way and will be in close aspect into February as Jupiter turns and moves direct. I rather think there is very much a synastry between Chiron and Jupiter, because Chiron in mythology was a Centaur and Jupiter's sign Sagittarius also represents a Centaur. Chiron was also a teacher and a knowledgeable one too and of course Jupiter rules knowledge and wisdom. Chiron in the old stories suffered a potentially fatal wound by being hit by an arrow from Hercules, but was granted immortality by the Gods, so in effect he became a healer who could not heal himself. Chiron rules wounding and healing, and some people think because of his erratic orbit around the Sun that Chiron is also a bit of a maverick influence.
Now interpreting Jupiter square Chiron is tricky, because of the myriad of possibilities we have here. Will Chiron cause a wound because of Jupiter need to explore and experience new things. Jupiter tends to take chances and here you open yourself out to harming yourself. Jupiter also encourages expansion, and maybe any wound will come because you are over extending yourself. On the other side of the coin, Chiron can heal you by curbing your excesses. Go on a diet for example or give up smoking or drinking too much. Maybe Chiron will force you in to healing your financial situation by encouraging you to cut your cloth accordingly? It all depends where in your chart this mutable square is activating.
As this is a mutable influence, this change will slightly easier to achieve than if it were a fixed square for example; fixed ones often need a really painful break in your behaviour before you learn to change your ways. In a mutable square you can change your direction by simply adjusting your manner of doing things, not to say this is still going to easy to achieve.
With both these bodies promoting wisdom and knowledge, this could be an excellent time to do some studying so that you might learn something very valuable for the future. Maybe someone of knowledge and experience will come along now, enter your life and give you a helping hand?
In this aspect, we still may have to face painful truths about ourselves and about where we are going wrong in out lives. This aspect does give us a chance to do something about them before it is too late. Especially as this square is still active after Jupiter turns direct on 31st January, you can use Jupiter's forward motion to start to open out and to learn some of the lessons from the past. It's time for some redemption in our lives, a chance to correct some of the mistakes we have made, and to become wiser and stronger in preparation for the next stage of our development...