The article discusses how to match up long and short positions in a tax straddle, addressing questions about liabilities and positions in a corporation’s own stock. The tax straddle rules aim to prevent taxpayers from deducting losses without real costs, aging holding periods artificially, or converting short-term gains into long-term gains. The rules were broadened in 1986 and amended in 2004, but some conceptual questions remain unanswered. The focus is on timing and holding period arbitrage, providing a historical overview and summarizing the rules for readers unfamiliar with them.