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How is one supposed to develop rapture? It doesn't seem like something you can just decide to attain. Any states that or may not have been rapture that Ive ever experienced happened during retreat when meditating all day everyday and even then it seemed to have happened by itself not because I was trying to make it happen.

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Rapture born of concentration (samadhi) happens by itself. For example, the sutta SN 48.10 says the rapture of jhana is born from making 'letting go' the object of meditation. Rapture is a reward for giving up craving. The less craving, the more 'progress'. What is 'cultivated' is giving up craving.

If there are doubts about this, the Anapanasati Sutta literally says:

A mendicant develops the awakening factor of rapture, which relies on seclusion, fading away and cessation that ripen as letting go.

MN 118

For a more detailed explanation, Ajahn Brahm has taught:

The rapture and bliss of jhana is directly related to the amount of Samsara which is, albeit temporary, let go of.

In meditation, pitisukha refers only to that joy and happiness that is generated through letting go.

The joy and happiness that arises with the beautiful breath is fueled by the letting go of burdens such as past and future, internal commentary and diversity of consciousness. Because it is a delight born of letting go, it cannot produce attachment. One cannot be attached and letting go at the same time. The delight that arises with the beautiful breath is, in fact, a clear sign that some detachment has taken place.

One might propose three major types of pitisukha, (joy and happiness): that generated by sensual excitement, that cased by personal achievement, and that born of letting go. Not only are these types of happiness differentiated by their cause, but they are also very different in their natures. The happiness generated by sensual excitement is hot and stimulating but also agitating and consequently tiring. It lessens in intensity on repetition. The happiness caused by personal achievement is warm and fulfilling but also fades quickly, leaving a sense of a vacant hole in need of filling. But the happiness born of letting go is cool and very long lasting. It is associated with the sense of real freedom

Sometimes meditators wonder about the role of effort in meditation. At the stage of meditation just before the beautiful breath, one’s effort should directed only into the knowing, and kept away from the doing mind. When effort is channeled into doing the meditation, that is, controlling everything, then the energized “doer” moves into restlessness, another of the hindrances. But when the effort is removed from the “doer” and is given fully to the knowing, then not only does restlessness disappear, but so does sloth and torpor.

Thus one cannot will the mind to be still! The way into stillness is though the pitisukha born of letting go. Once the delight that comes with the beautiful breath appears, then will becomes redundant. It becomes unnecessary since mindfulness stays with the breath all by itself, effortlessly. Mindfulness enjoys being with the beautiful breath, and so does not need to be forced. It is through the arising pitisukha at the stage of the beautiful breath that will becomes calmed, effort is relieved, and stillness begins to manifest. When stillness appears it enriches the pitisukha. The deepening of pitisukha, in turn, creates even less opportunity for effort, and so stillness grows stronger. A self-reinforcing, feedback process ensues. Stillness deepens pitisukha. Pitisukha increases the stillness. This process continues, when not interrupted, all the way into Jhana where stillness is profound and pitisukha ecstatic.

The Jhanas: Ajahn Brahm

Ajahn Buddhadasa, similar to Ajahn Brahm, previously explained:

In this lecture we will speak about the second tetrad of Anapanasati. These four steps deal with the feelings and are called "vedananupassana (contemplation of feeling)." The first two steps of this tetrad take piti (rapture) and sukha (happiness) as the objects of our further study and detailed examination.

The practice of these steps develops out of the practice of the previous step. Once the body-conditioner or breath is calmed, the feelings piti and sukha appear [by itself]. Then, we take these very piti and sukha as the next objects or materials of our practice.

If we calm the kaya-sankhara (body-conditioner) to the extent of jhana (the first jhana and so forth), then piti and sukha will be full and complete as factors of jhana. Nevertheless, if we are unable to reach jhana and are able only to calm the body-conditioner partially, there is likely to be a degree of piti and sukha proportionate to the extent of that calming. Thus, even those who are unable to bring about jhana can still manage enough piti and sukha to practice these steps.

Anapanasati: A Manual for Serious Beginners

Another Anapanasati book by Ajahn Buddhadasa explains:

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    I don't know why people downvoted this answer as it is quite complete. the simple fact is rapture is a factor gained from concentration, jhana.
    – Remyla
    Jan 25 at 9:38
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    people want to think their superficial fondlings with meditation are jhana. the Tibetan guru Chögyam Trungpa called this 'Spiritual Materialism' or 'ego'. Jan 25 at 9:56
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    Irony of all this is that the Buddha said that the dharma leads to dispassion and relinquishment, not passion and accumulation.
    – Remyla
    Jan 25 at 10:51
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Developing rapture is very important. There are various ways to do it. If you are convinced that you will not hurt anyone at any cost then you should feel the rapture. It needs to be developed. Unlimited compassion is the basis of rapture because you have understood that everyone is going to suffer. If you have renunciated possessions then also you should feel the rapture as you are on the right path. If you have understood impermanence then also you should feel rapture because that is the nature of all conditioned phenomena. If you have understood all Dhammas as not self then also you should feel rapture because it is very difficult to discern this fact.

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If you examine Vedana closely you will realize how they form. Vedana is divided into 3 categories.

  1. Pleasant
  2. Unpleasant
  3. Neutral

Pleasant feelings(Vedana) occurs when it(sensory object) is agreeable to other perceptions and mental states. Unpleasant occurs when it's disagreeable. Neutral feelings occur when it's dull and uninteresting.

The same sensations may give rise to pleasant feelings at one time and unpleasant feelings the next time.

If you understand how Vedana rises you can see how rapture rises from meditation. i.e Reduce desires and thus every sensory object becomes agreeable(pleasant).

If you examine more, you can try to manufacture rapture at will. This process is what I call "developing rapture".

Some people intuitively understand rapture due to long time exposure, and some can examine it more closely to understand it's causes.

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AN 11.3:

When there is no joy, one who lacks joy has destroyed a vital condition for rapture. Pāmojje asati pāmojjavipannassa hatūpanisā hoti pīti.

I think it means you should enjoy the Dhamma, not just pout about it. If you enjoy it then you will pursue it and cultivate path factors. It makes sense that Dhamma is more likable on retreat where there's less distraction - then you can really get into it and increase the probability of taking what some call path action. When you take path action you get path re-action, like rapture.

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