1. Introduction
2. History
I. The hard law of the conditional bond
II. Early common law authorities
III. First Stage of development c.1480: the prevention of double recovery on a simple bond
IV. Second Stage of development c.1601: the equitable restraint of common law rights in cases of accident, mistake, hardship, trifling and fraus
V. Third Stage of development c.1660: security of collateral rights and the foundations of the modern law
VI. Fourth Stage of development c.1800: the parties' purported intentions
VII. Fifth Stage of development: the decline of the intention-based approach in the early 20th Century and the decision in Dunlop Pneumatic Tyre Co
VIII. Summary
3. Two approaches
I. Removing the breach of contract requirement and the decision in Andrews
II. The Australian security rights approach: legal history
III. The Australian security rights approach: policy and morality
IV. Three objections to the Australian penalties doctrine
V. The English secondary rights approach: preserving a legally imposed regime remedying breach of contract
VI. Summary
4. Other justifications for the penalties doctrine
I. The penalties doctrine does not preserve economically efficient outcomes
II. The penalties doctrine does not simply prevent deterrence
III. The penalties doctrine is not about preventing the creation of perverse contractual incentives
IV. The penalties doctrine is not about preserving B's liberty of action
V. The penalties doctrine is not about alleviating deficiencies in contractual risk calculation and bargaining position
VI. The penalties doctrine is not about preserving substantive contractual fairness
5. Engagement
I. Threshold test under Australian law: is the impugned agreed remedy a security right?
II. Threshold test under English law: is the impugned agreed remedy a secondary right?
6. Punishment
I. Recent developments
II. Seven principles
III. Justifying the legitimate interest standard
7. Remedies
I. Restatement of the Australian position: remedial consequences of a finding that a clause is penal
II. Restatement of the English position: remedial consequences of a finding that a clause is penal
III. Agreed remedies, penalties and potential limits on recovery
8. Interplay between legal rules
I. Does the Australian penalties doctrie consist of two distinct rules or a unified rule?
II. Relief against penalties in the context of deposit clauses
III. The relationship between forfeiture and penalties
9. Conclusions
10. A codified guide to the penalties doctrine.