Yes, the landlord can sue the tenant for rent owed as well as any other damages in a Civil Action or through Small Claims. The procedures for Civil Actions are governed by the Massachusetts Rules of Civil Procedure. Normally, it would be advisable to hire an attorney before suing a tenant for money damages in a Civil Action. Small Claims, on the other hand, was designed to assist litigants who wish to proceed without an attorney. There is normally a $2,000.00 ceiling on the amount of money damages that can be sought. Thus, if a tenant owes $4,000.00 in rent, at the time that a Small Claims action is instituted, $2,000.00 of that amount will be waived. On the other hand, there is nothing to prevent a landlord from suing for rent as each month comes due, as long as the contract rent is not above $2,000.00.