Probationers often walk a fine line between scrupulously following the rules of their probation and “ratting themselves out.” Keeping an open line of communication between the probationer and his or her probation officer will foster good karma and a good relationship. On the other hand, it would not necessarily be a violation of probation to not tell them of circumstances, such as being kicked out of one treatment facility but enrolling in another.
Most rules of probation require the probationer to notify the probation officer if there have been new police contacts (obviously including a new arrest), new charges, a change of address, or a change of employment, etc.
However, whether a probationer should report depends on their personal situation. In the treatment example above, one option would be to not tell the probation officer about the failed treatment program and simply enroll in the new treatment program. Arguably, the probationer is still in compliance with their probation (unless they were required to complete a specific treatment program). However, odds are that treatment program number one will notify the probation officer about getting kicked out. It’s always worse if the probation officer finds out about a problem from someone other than the probationer.
Another option would be to enroll in the new treatment program and then tell the probation officer about the problems with the first program. Again, the probationer would likely not be in violation of their probation in that circumstance and they will be incurring goodwill with their probation officer by being upfront.
To a large extent a lot of these issues really depend on the relationship with the probation officer and how well things have been going. Sometimes probation officers are definitely out to get a probationer and this can make things difficult. On the other hand if there’s been good compliance and the probationer is honest, the probation officer will probably work with them.
Often the answer to this question is simply “It depends….”