Jupiter always represents where we should work our Karma through the expansion of self. The person never developed himself in a past lifetime and, thus, incarnated now as the same type of person that he was in the past. An entire lifetime was wasted and the tendency might be to waste this lifetime, unless the energy of retrograde Jupiter is transmuted. With a retrograde Jupiter, the person is redoing a lifetime from the past. Opportunities are in every lifetime and in every chart, but the individual determines his lives, for there is free-well. A person can either become a slave to his chart, can overcome it, or does not have to live up to any of it. As you sow, so shall you reap.
First House: Since we are again dealing with negative character traits, retrograde Jupiter in the 1st house would indicate that the native of the chart developed negative personality traits in a past lifetime, was unrefined and unreliable in judgment. The tendency of retrograde Jupiter to bring about a form of dishonesty or a lack of a sense of Justice towards others would depend largely upon the sign in which Jupiter would be posited in the 1st house.
Since Jupiter, as the natural ruler of the 9th house, also would be involved with a philosophical attitude, or irreligious inclination, a retrograde condition would make for a lack of sound philosophical approach to life, a strange, unorthodox religious approach, and a neglect of higher mind qualities. The person would tend to dissipate the energy of a retrograde Jupiter, often leading to alcoholism.
A question could very easily be posed here as to the basic honesty of the individual with regard to himself in relation to the rest of the world. Here self-deception could be quite noticeable and rather obvious.
The lesson to be learned, with a retrograde Jupiter in the 1st house, is to develop an awareness of self, to find a level of reality in which the individual would "know himself."
Second House: Retrograde Jupiter here relates to the material aspect of life since Jupiter represents money. This implies the proper use of money or the lack of value of money and possessions in the past. Stringiness, miserliness, the "Silas Marner" aspect of the past would be involved, having money and not using it properly, in other words.
It could imply, also, that the individual in the past had "good luck," could have inherited fortunes, and dissipated it all. Money implies responsibility, and the retrograde Jupiter shows that the responsibility of money (and possessions) was not properly assumed in past lifetimes.
Since Taurus is the natural ruler of the 2nd house, with Venus as the ruler of Taurus, it could indicate that the individual spent money unwisely on foolish, gaudy, "showy" type of home decorations, jewelry, etc.
Since retrograde Jupiter here opposes the 8th house, part of the karma involved relates to exposure in the past to Occult Metaphysics, but the individual either rejected it or neglected it.
The lesson to be learned, with retrograde Jupiter in the 2nd house, is to re-evaluate ideas about money and its proper use, true appreciation of whatever the native possesses, and the need for a definite alignment with higher truth in Metaphysical research.
Third House: Here the retrograde Jupiter is opposing the 9th house of higher education and religion and law. It definitely shows that good judgment was not used in whatever field of study the individual might have pursued, on either a lower or higher level of structured education. It also shows that, religiously the individual opposed organized religion, not so much from the faculty of reason, but rather the lack of good judgment and analysis. Here, the sign that Jupiter is in would demonstrate the reason for the lack of faith.
The element of prejudice also enters, as a subtle influence, when retrograde Jupiter is in the 3rd house, since it causes reaction in the 9th house.
Retrograde Jupiter tells that the relationships with brothers and sisters left much to be desired with, certainly, a lack of tact, dignity and honor in connection with siblings and other relatives.
The native certainly was not a responsible individual, could not keep confidences and, so, was untrustworthy. It certainly proves that the individual would not avail himself of the learning facilities which would have brought about a development facilities which would have brought about a development of skills and traits of character and personality.
This location of Jupiter is important in that it completes the development of the "I" in relationship with the rest of the world (house 4,5,6). Therefore, the retrograde Jupiter tells that the native's development of the "I" concept resolved itself into a self-centeredness rather than a self-awareness, so that the relationships, as indicated by the rest of the quartiles of the horoscope, centered around an egocentric direction of energy. The individual saw the world in relationship to himself rather than seeing himself in relationship to the world. This is further emphasized by the fact that Jupiter is the natural ruler of Sagittarius, a self-centered sign of the Zodiac.
The lesson to be learned with retrograde Jupiter in the 3rd house is the proper realization of the "self," which would have to begin with the immediate family members, schoolmates, neighbours, etc. The energy of Jupiter would have to be directed with purposeful determination towards worthwhile goals, and he would have a develop a tactful, dignified, sincere channel of communication with those who enter into his sphere of influence.
Fourth House: Retrograde Jupiter in the 4th house stresses that, in the past, the development of the "I" concept was accomplished along negative lines. The individual lacked compassion, generosity, sociability, broadmindedness. It shows that the environment established in any home relationship was very much a one-sided affair, for the individual had to be the absolute ruler with absolute power. There was no room for differences of opinion or consideration of others' needs or wants in so far as this individual was concerned in the past. Although disliking restraint himself, he imposed restraints, limitations, discipline on others under him within the home circle.