In what situations can letting go of attachments be painful? From what I understand of the Buddhist path, letting go of attachments shouldn't be painful. Are there times when letting go will be painful and if there is, why are those times different than the usual?
From what I understand of the Buddhist path, letting go of attachments shouldn't be painful.


Working through deep-rooted states of stress and mental hindrances can be both unpleasant and painful. The pain is not really a problem. It's just another object to work with, to observe and to cultivate insights from.

The real problem is our reaction to the pain. The judgement, the inclination, the liking/disliking that goes on.

That behavior is what shapes the tendencies of the mind. It will like certain experiences and be aversed towards other experiences. In that way ones happiness and peace of mind, is dependent on a certain set of causes and conditions. The mind is not free as long as it clings.

This shows us that we have work to do and where it has to be done. The goal is to be able to experience the full spectrum of experience without falling into suffering.  


  Are there times when letting go will be painful and if there is, why are those times different than the usual?


The suffering one experiences, when renouncing an object, is directly proportional to the attachment one has cultivated towards that particular object/experience.