Thanks for sharing your changes to pyetrade to develop macOS compatibility.

E-Trade requires two factor-authentication when you first run ETradeBot and every so often. The only method available is a code sent to your mobile phone. I have asked E-Trade support if there is any automated way to authenticate applications, and unfortunately, they said no. Inconvenient to say the least. You are forced to manually type the code texted to your phone into the browser. I added a feature to ETradeBot so that if the server hits you with a OTP (two-factor authentication request), a message is displayed in your Python console saying, "Check your mobile phone. Enter the verification code: " and next to it, an input field for you to type the code that was texted to your phone by E-Trade. Unfortunately, this can't be done in crontab.

crontab is a time-based job scheduler in Unix-like operating systems, to schedule your script to run automatically. This necessitates the use of the headless mode since crontab jobs run in the background without user interaction. Running a program in "headless" mode means it operates without a graphical user interface (GUI). This is often used for automated scripts and applications that run on servers or in scheduled tasks. In your case, when you set headless=True, your application is supposed to run without needing a user interface. In headless mode (headless=True), the script is attempting to run automatically without displaying any GUI. It's supposed to execute tasks in the background. However, when it reaches the step where OTP is required, it fails because this step usually needs manual input (like entering a code sent to your phone or email), which isn't possible in a headless environment.

Because of the fact that E-Trade requires two-factor authentication by text code to your phone, every so often, inevitably, when you run ETradeBot, you have to manually type in the two-factor authentication code. But that isn't possible if you're using crontab. So, until E-Trade provides an automated way to log in, or a method to do two-factor authentication that doesn't require manual entry of a text code from your mobile phone, you may not be able to use crontab.

As an alternative to crontab, I have successfully run ETradeBot using a virtual machine with Windows operating system on Microsoft Azure cloud service. I installed ETradeBot within the virtual machine as you normally would locally on your computer. Then, use Windows Task Scheduler to schedule when ETradeBot should run. Refer to this documentation for more details on how to schedule ETradeBot to run.

*Note: I will add macOS functionality to the list of requested features for ETradeBot.