Ella Freeman Sharpe Interpretation: Seeing people in jail foretells small worries for the dreamer, such as disappointment in associates, or losses due to negligence on the part of others concerned.
A jailer in the dream is another form of a wish to elude responsibilities that have become unbearable.
If the jailer is with other people then the dreamer would like to eradicate them. Just to see a jail may be a guilt complex for some very minor infringement of the law such as a traffic violation.
See Prison.