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Let’s look at important things here –
Jupiter - It is the most benefic planet and it represents all the auspicious things like Knowledge, Wisdom, Law, Guru, Spirituality, Religion, Philosophy, Literature, Elderly People and Children etc. For a girl, Jupiter also represents Husband.
Ashlesha - Ashlesha represents our insecurities and weaknesses as a human being. It is a nakshatra of clinging on to someone or something. It also represents psychological issues. For more information on Ashlesha Nakshatra, please check this link - https://www.astrosaxena.com/Ashlnaksh .
Cancer - As Ashlesha is a part of Cancer, Cancer sign and its representations become important. Cancer is 4th sign of Zodiac Belt, hence it represents the things represented by 4th house like Mother, Mother's Care, Emotions, Taking Care of Others and Nourishment etc. Cancer is consisted of 2 and half Nakshatras namely Punarvasu, Pushyami and Ashlesha. Cancer's lord is Moon, which again represents almost same things which Cancer and 4th house represents.
Moon - As Moon rules Cancer, Moon's position and dignity is important to know about the overall functioning of any planet in Ashlesha/Cancer.
Mercury - As Ashlesha is ruled by Mercury, Mercury's position and dignity will also have an important role in functioning and results of any planet in Ashlesha.
Houses Involved – Also, we can’t afford to forget the houses involved as a planet can be ruling different houses and sitting in different house for every person as per ascendant and planet’s position. To know overall affect, we have to consider the houses involved as those areas of life are being impacted.
Interpretation of Jupiter in Ashlesha Nakshatra – Although, Jupiter is in exaltation sign still but it is in enemy nakshatra of Mercury. Moreover, the nature of Ashlesha is not great anyways. As Ashlesha shows our insecurities & clinging attitude and as Jupiter is all about expanding things, this position can expand those insecurities. It can make person much more insecure and they can be very possessive about things or people. Also, Jupiter in Punarvasu/Pushya can be about serving others through knowledge without any selfish interests but Jupiter in Ashlesha may not be so unselfish. Because of their insecure nature, they can become all about safeguarding their own interests before providing any services to others. They can be clever or cunning too. This is all result of their insecurities which is making them behave in this way. So, they can still be good teachers and share their knowledge with others but they may not be selfless.
As Ashlesha is about clinging and represented by entwined snakes, in relationship matters also this insecure nature shows up and person can be clinging to their partner. Sometimes they don't even know that they are clinging on to a poisonous snake like person.
So, the biggest challenge for them is to overpower this feeling of insecurity. They need to realize that nothing and none is going to stay forever with anyone. Once they have this realization then same position can be utilized in spiritual pursuits, meditation and kundalini awakening.
Role of Moon – Moon's placement is important to guide Jupiter in right direction, being Cancer's lord.
Role of Mercury - Mercury's placement is important to guide Jupiter in right direction, being Ashlesha's lord.
Other Factors – And of course, we need to consider conjunction, aspects, house lordship, house position and dashas etc to know the exact results of Jupiter in Ashlesha. So, we always need to take a holistic view of chart rather than just 1 planetary position.
Conclusion – So, this is how I see Jupiter in Ashlesha can work in a chart.