How Toll Booth works

1. Set up your account and connect Schwab

You create a Toll Booth account, review key terms, and connect a Charles Schwab account using Schwab's OAuth sign-in. You sign in directly at Schwab; Toll Booth never sees or stores your Schwab username or password.

Before connecting, ensure you have covered-options trading approval on your Schwab account. The detailed onboarding steps are outlined on the Get Started page.

2. Choose guardrails and preferences

Inside Toll Booth, you decide which symbols are eligible, how much of each position can be used for covered calls, and how the system should react to price moves. These settings act as guardrails for when the automation can place or adjust trades on your behalf.

You can start conservatively and adjust over time. Trading can be paused or disabled if your situation or preferences change.

3. Covered-call lifecycle

Once enabled, Toll Booth monitors your eligible positions and looks for covered-call opportunities that fit your configuration. When the system identifies a trade, it submits orders through Schwab within the permissions you have granted.

The covered-call lifecycle is documented in more detail on the technical pages:

• Opening — how new covered-call positions are opened.
• Selection & Pricing — how strikes and expirations are chosen.
• Rolling — how positions may be extended or adjusted over time.
• Closing — how gains and risk are managed when conditions change.

4. Safeguards and controls

The system is built around guardrails intended to limit risk and keep behavior aligned with your settings, such as conservative strike selection, caps on how much of a position can be used for covered calls, and rules for when to roll or close.

You always retain control: you can change preferences, pause trading, or disconnect your Schwab account. Toll Booth does not move cash between institutions and does not have money-movement permissions.

5. Reviews, notifications, and examples

As positions evolve, you can review activity and notifications in Toll Booth and at Schwab. Outcomes will vary over time, and it is important to periodically review positions, risk, and configuration choices.

For illustrative, hypothetical examples of how covered calls can affect cash flow and risk, you can explore:

• Covered call life cycle example
• Covered call premium yield example
• Bull put spread overview (hypothetical example only)

These examples are hypothetical and for illustration only. Actual outcomes will differ based on markets, timing, and your portfolio.

Next steps

If this process fits how you want to approach covered calls, you can review pricing and start the onboarding flow.

• Revisit What is Toll Booth
• Review pricing
• Get Started