How Toll Booth works

You should have a basic understanding of what a covered call is and what it means for your shares before using Toll Booth. The platform automates execution, but you are responsible for understanding the strategy and configuring it correctly. If you're new to covered calls, read the sections above before using the platform.

You can run covered calls on any stock you hold at least 100 shares of, as long as it has a listed options chain and your Schwab account is approved for covered call writing. Toll Booth will identify eligible holdings in your account automatically.

Your shares may be sold ("called away") at the strike price at expiration. You keep the premium you collected, but you give up any appreciation above the strike. Toll Booth can be configured to roll positions before expiration to reduce this risk, but rolling cannot eliminate it — especially in fast-moving markets.

Yes. The premium you collect does not protect against a stock declining in value. If a stock drops significantly, the option premium is unlikely to offset the loss. You also risk having shares called away at a price below what you could have sold them for if the stock continues to rise. Results depend on market conditions, your holdings, and how you configure the system.

$100 per month, with no setup fees. You can cancel anytime. Standard Schwab brokerage commissions on options trades still apply separately. See the pricing page for full details.

Toll Booth connects using Schwab's official OAuth API. It receives a limited-access token — it cannot withdraw funds, transfer assets, or change account settings. Your login credentials are never shared with or stored by Toll Booth.

Yes. You can cancel your Toll Booth subscription at any time. Open positions in your Schwab account are yours — cancelling Toll Booth does not close or alter them.

Yes — Toll Booth was designed to be flexible. You can continue to place, modify, or close orders directly in your Schwab account at any time. Toll Booth monitors your positions and will adapt accordingly. If you prefer to manage certain positions yourself and let the automation handle the rest, you can exclude specific holdings from Toll Booth's configuration so it only acts where you want it to.

No. Toll Booth is automation software that executes a strategy you configure. It is not a registered broker-dealer or investment adviser and cannot assess whether this strategy is appropriate for your specific financial situation, goals, risk tolerance, or tax circumstances.

At this time, Toll Booth only places orders for covered call positions. Support for equities and other option strategies may be considered in the future.

One of the less obvious tax dynamics of covered calls comes from rolling. When Toll Booth rolls a covered call — closing the existing short call and opening a new one further out — it collects a net credit overall, but the closing leg is almost always a loss: you buy back the call for more than you originally sold it for. That closing loss is a realized loss for tax purposes, even though the roll as a whole was profitable. Over time, rolling can generate a stream of deductible losses that offset gains elsewhere in your portfolio, all while the strategy continues to produce net income.

This effect is most pronounced on rolls where the underlying stock has moved against you and the call has appreciated significantly — exactly the scenario where the position needs rolling most. The new short call collected on the opening leg is income, but it is typically recognized in a future tax period when that leg eventually closes.

In taxable accounts, covered calls also let you generate income from shares you already own without triggering a sale, deferring any capital gain on the stock itself until you actually want to sell. Tax treatment depends on your specific situation, holding periods, and jurisdiction, and the wash-sale rules can interact with options in complex ways. This is not tax advice; consult a qualified tax professional.