Overview
Option Strategies Insider is run by Chris Douthit and built around several things most single-product alert services don't combine: a weekly Executive Report of options trade ideas, a separate stock portfolio for members who also want longer-term stock picks, daily market updates that keep members oriented between alerts, and coverage of both long-term and short-term options strategies rather than one fixed timeframe. Each Executive Report recommendation includes the reasoning behind it, not just a ticker and a strike.
That combination is what separates it from a typical options newsletter: most competitors pick one lane, a handful of monthly alerts, or a single trading style, and stop there. OSI pairs its trade ideas with daily market context and a curriculum built to actually teach the mechanics, not a slide deck bolted onto a sales page.
What you get
Membership centers on the Executive Report, but several things underneath it are what separate this from most alert services:
- A real curriculum, not a slide deck. The free three-tier course (25 lessons total) is built to actually teach options mechanics, not just tee up a sales pitch, which is the more common pattern among paid alert services that treat education as an afterthought or a separate upsell.
- A stock portfolio included alongside the options alerts, so members who also want longer-term stock picks aren't limited to an options-only feed.
- Daily market updates that give members context between Executive Report alerts, instead of going quiet until the next weekly trade idea lands.
- Both long-term and short-term options coverage, rather than committing to one trading style the way most single-focus alert services do.
Beginning Options
8 lessons covering the fundamentals
Intermediate Options
6 lessons on structuring trades
Advanced
11 lessons on risk-focused strategy
What an alert looks like
This is an illustrative structure only, not an actual historical trade.
Pricing
OSI's Ultra membership runs $99 a month, covering the weekly Executive Report, the stock portfolio, daily market updates, and the full three-tier curriculum. Confirm current terms and any active promotions on OSI's own sign-up page before subscribing.
Pros and cons
What stands out
- Free education is substantial, not a teaser for a paid upsell
- Reasoning shown per trade, not just a ticker
- Combines options alerts with a stock portfolio, rather than an options-only feed
Where it falls short
- No public win-rate or track record posted on the homepage
- Detailed membership pricing isn't visible until sign-up
- Single-analyst dependency, not a team of contributors
Verdict
Combine a weekly Executive Report with real reasoning shown, a stock portfolio for members who also want longer-term stock exposure, daily market updates, coverage of both long-term and short-term options trading, and a curriculum with actual depth behind it, and you get one of the more complete trade-advisory packages available rather than a single-product alert feed. That combination is why we rank it #1 in this category. The lack of a public track record is the main thing worth pressing on before subscribing.
Frequently asked questions
Is Option Strategies Insider worth it?
For traders who want options-specific ideas with the reasoning explained, plus daily market context and a real curriculum rather than a bare alert feed, it's one of the more complete packages we've reviewed in this category.
Does Option Strategies Insider trade both short-term and long-term options?
Yes. Unlike most single-focus alert services, it covers both long-term and short-term options strategies rather than committing to one trading style.
What's included in Option Strategies Insider's education?
A free three-tier curriculum covering options fundamentals through advanced, risk-focused strategy (25 lessons total), built as an actual course rather than a sales-page slide deck.
Does Option Strategies Insider offer stock picks too?
Yes. Alongside the options-focused Executive Report, Ultra members also get a stock portfolio, so the membership isn't limited to options-only ideas.
Ready to try Option Strategies Insider?
Free lessons, weekly Executive Report alerts, a stock portfolio, and the $99/month Ultra membership. See current terms on their site.
Sign up at Option Strategies Insider →