One of the basic assumptions of accrual accounting is that, in due time, revenue earned in the normal course of business will be collected and liabilities incurred will be paid. Yet, case law indicates that it is inappropriate to impose the income tax on amounts whose collection is reasonably in doubt, even though these amounts are fixed, determinable, and undeniably due the taxpayer. In such an event, taxpayers can either exclude the income item from gross income, viz., the common law doubtful collection exception, or include the item in gross income and charge bad debt expense upon specifically writing off the matching receivable. While the common law doubtful collection exception is conceptually sanctioned by the tax court and the Federal Circuits, conflict exists concerning the level of financial distress required to establish reasonable doubt and the exact point in time when such distress must exist. More important, given that the common law doubtful collection exception is independent of the highly developed body of statutory, regulatory, and case law governing bad debt deductions, opportunities for the common law exception may exist where either the bad debt deduction is unavailable or additional steps are required to sustain the deduction. Conversely, the possible inability of an accrual basis taxpayer to actually pay an expense that meets the three-prong all events test does not, in itself, preclude a deduction of that expense, even where the inability to pay exists at the time of accrual. Thus, where a liability accrues under the three-prong all events test, even the strong likelihood of nonpayment due to the taxpayer's insolvency will not necessarily prevent its accrual and deduction. While several Federal Circuits permit accrual and deduction, even in situations where an obvious inability to pay exists at the time of accrual, the tax court and other Federal Circuits condition accrual and deduction on the taxpayer having a reasonable expectation of payment at the point of accrual. However, even when a deduction meets either of the above tests, the commissioner can still argue that, under the Mooney Aircraft common law economic performance requirement, the deduction does not clearly reflect income. This article explores these apparently conflicting treatments of accruals with the aim of providing tax specialists with a practical yet authoritative guide to the possibilities of income deferral and expense accrual (i.e., acceleration) in instances of reasonable doubt as to ultimate collection or payment.