Options Boot Camp 409: The Madness, Mystery and Mayhem of Expiration

When does an option actually stop trading, and what happens when expiration arrives? Mark Longo and Dan Passarelli trace how the calendar grew from monthly expirations to weeklies, daily SPX options, and Monday and Wednesday expirations in select stocks and ETFs. Along the way, they explain why traditional SPX monthly options can stop trading on Thursday yet settle on Friday morning, how cash settlement differs from physical settlement, and why expiration day can catch traders off guard. They also share stories from the trading floor and answer listener questions.

Yacht rock piracy meets options strategy on this episode of Options Boot Camp. Mark Longo and Dan Passarelli break down Dan's "net zero roll" for cash-secured puts, including how traders can roll down and out while targeting little or no net premium on the adjustment. They also tackle a fresh batch of listener questions covering how implied volatility can help determine whether to buy calls, sell puts or use call spreads; how much open interest and volume really matter when selecting a strike; what steep put skew can reveal when VIX isn't moving; and whether traders put too much emphasis on dealer gamma positioning. Plus, the Boot Camp crew digs into pin risk in the era of daily and short-dated expirations, looks at which options strategies might deserve the full book treatment, checks in on the latest 0DTE butterfly poll results and, naturally, investigates Dan's alleged yacht rock piracy on the Chicago River.

The iron butterfly is getting a 0DTE makeover. On this episode of Options Boot Camp, Mark Longo is joined by Dan Passarelli and John Kmiecik from Market Taker Mentoring for a deep dive into the growing world of zero-days-to-expiration iron butterflies. Why are traders turning to this classic options strategy for ultra-short-term trades? John breaks down how he approaches 0DTE iron butterflies, including timing his entry after the open, choosing spread widths, setting profit targets, managing risk, and taking advantage of changes in implied volatility and time decay. The crew also explores 0DTE double calendars, whether these strategies could work in single-stock options, managing a calendar that has moved away from its strike, and the most overrated advice in options trading.

Is the earnings volatility worm finally starting to turn? On this episode of Options Boot Camp, Mark Longo and Dan Passarelli dig into the latest earnings options data and examine whether the recent run of dominance for premium buyers may finally be losing steam. They break down how actual earnings moves are stacking up against what the options market priced in, whether traders should be rethinking the buy-vs.-sell premium equation, and how Dan approaches earnings trades using time spreads, double calendars and other volatility strategies. Plus, the Boot Camp instructors tackle IV Rank, zero-DTE butterflies, buy writes, options volume by exchange, binary options and prediction markets, and much more.

On this episode of Options Boot Camp, Mark Longo and Dan Passarelli tackle the challenges and opportunities of trading options in a low-volatility market. Should you still be selling premium when volatility is cheap, or does low vol make buying options more attractive? Are single-stock options offering better opportunities than index options in the current dispersion environment? The Boot Camp instructors break down how they're approaching these markets and where they're still finding opportunities. Then they examine the strange recent VIX glitch that briefly sent the cash index soaring while VIX futures barely moved. What caused it? Could traders actually take advantage of it? And could resting "wishlist" orders help you capitalize when markets briefly get out of line? Plus, the instructors discuss the biggest forces driving the market right now, revisit perpetual futures, and share an update on the potential Options Boot Camp reboot. Topics include: Trading options in a low-volatility environment Buying options vs. selling premium when volatility is cheap Single-stock options vs. index options Dispersion and individual-stock volatility The mysterious VIX glitch Why VIX futures didn't follow the cash spike Using resting "wishlist" orders for unusual market moves Perpetual futures and market liquidity What's driving the market right now

The double calendar saga continues! On this episode of Options Boot Camp, Mark Longo and Dan Passarelli head back into the trenches for another deep dive into double calendar spreads—this time focusing on one of the biggest questions from listeners: How do you actually manage these trades once they're on? Dan breaks down his approach to double calendar management, including what happens when the underlying tests a strike, why modeled break-even points matter, when he takes profits, and when it's time to cut bait. The discussion also explores using double calendars in SPX versus individual equities and whether this strategy could provide an interesting alternative way to capture weekend market moves. Then it's time for listener questions covering: When low volatility makes outright calls or puts more attractive than debit spreads How Dan selects strikes when trading the wheel The role of technical levels and premium when selling options What happens when you correctly predict a stock's direction but still lose money to an implied volatility collapse Why volatility analysis matters before entering an options trade It's Double Calendars Part 2. The stakes are higher. The calendars are doubled. And this time...it's Electric Boogaloo!

What do double calendar spreads and the Fall of Constantinople have in common? More than you might think. On this episode of Options Boot Camp, Mark Longo and Dan Passarelli use a memorable historical analogy to explain one of Dan's favorite advanced options strategies: the double calendar spread. The discussion covers: What a double calendar spread actually is Why it can be viewed as a "strangle swap" How Dan structures weekly double calendars When he typically enters and exits the trade Why wider breakevens aren't always guaranteed A recent SPX double calendar example Managing profits and avoiding common mistakes Then it's time for listener questions covering: Selling cash-secured puts versus covered calls near market highs Trading calendars and diagonals during earnings season Whether buying options into earnings still makes sense Scaling into positions Weekly SPY options and whether traders are sacrificing edge for more opportunities

The Warren Buffett conversation continues! After the response to our 400th episode, Mark Longo and Dan Passarelli head back to the mailbag to tackle even more listener questions about the Oracle of Omaha and his approach to options. On this episode, we discuss: Are covered calls compatible with Buffett's buy-and-hold philosophy? Would Buffett ever use LEAPS instead of buying stock? Is "getting paid to wait" really the same thing as selling option premium? Does Buffett care about implied volatility when selling options? How might Buffett use options once he owns a stock he plans to hold forever? The unusual economics behind some of Buffett's legendary long-term put trades Why the "magical Buffett premium" may be something ordinary options traders can only dream about Plus, a trip deep into the Options Boot Camp archives

Can one of the world's greatest long-term investors teach options traders a thing or two? To celebrate the 400th episode of Options Boot Camp, Mark Longo welcomes Dan Passarelli and special guest Russell Rhoads for a fascinating deep dive into Warren Buffett's real options strategies. While Buffett famously called derivatives "financial weapons of mass destruction," the reality is far more nuanced. The panel explores how Berkshire Hathaway has used cash-secured puts, covered calls, long-dated index options, warrants, and over-the-counter derivatives to build positions, generate income, and manage risk. The discussion also covers Buffett's famous global index put trades, why he prefers selling puts to enter positions, how he thinks about valuation, risk management, and knowing when to admit mistakes. Whether you're a buy-and-hold investor or an active options trader, this milestone episode offers timeless lessons on patience, discipline, and using options as investing tools rather than speculation. In this episode: Celebrating 400 episodes of Options Boot Camp The truth behind Buffett's "financial weapons of mass destruction" quote Why Buffett sells cash-secured puts Covered calls and long-term investing Buffett's legendary global index put trades OTC derivatives vs. listed options Risk management lessons every options trader can use Buffett's biggest investing mistakes—and what they teach us

Mark Longo and Dan Passarelli dive deep into the mailbag to break down the mechanics behind the explosive growth of the options market and answer your burning strategy questions. The guys unpack a historic month in the industry—June 2026 pulled in a mind-blowing 1.6 billion contracts—and debate what this massive wave of liquidity actually means for retail traders. Is the market becoming too efficient, or are the opportunities bigger than ever? Topics covered in this episode include: The Record Volume Boom: A look at the staggering numbers from 2017 to today. How the pandemic structurally changed options trading forever, and where the peaks and troughs of liquidity hide. Mastering the Wheel Strategy: Dan addresses his "mythical" $30 threshold and explains the exact circumstances under which he'll run a wheel trade on a stock under $5 (including a look at his current covered strangle on a $4 stock). SpaceX ($SPCX) Options Pain: Two weeks post-IPO, the guys analyze the action, the crushing moves, the symmetry of iron flies, and why cutting losses early on a juicy but volatile setup is a rite of passage for successful traders. The Hardest Lesson in Trading: Why your exit strategy matters vastly more than your entry plan.