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It wouldn't be hard but you are essentially at the IRS's mercy in terms of how your trades are qualified if you don't segregate properly.

You are correct, but you might not sell those shares the next year or the year after that so the gain could be deferred indefinitely. The IRS wants its money now!

It is a gray area, but if you mix and match like this, the IRS might try to categorize your trading in the way that makes it most profitable for them. To be safe, you should segregate your investments from your trading by using different accounts. Even then, if you are trading the same...

If the wash sale rule didn't exist, you could sell all your losers at year end and then immediately buy them back in order to defer taxes. The IRS wants their fair share.

It isn't just futures where IB's price capping algorithm rears its ugly head. I have had numerous problems with price capping for stocks during recent market volatility. I have complained incessantly to IB about not being able to control my risk and they just don't listen. You can remove price...

They've got to have timestamps (both submission and execution) on your orders and there has to be a way for you to get those details (plus maybe what type of order it was). Then maybe you can figure out exactly when this phantom order was submitted and executed. I've had busts get reported to...

What if they come back later and say that the extra contract was in error and it is now busted? If it were me, I would be asking for complete trade logs for that day and trying to figure out what the hell happened. Because I've seen some weird stuff happen and it is not out of the realm of...

And if you look what happened when they instituted a short ban, the market really plunged. Maybe they have learned their lesson, but probably not.

If this is the case, then you need to contact etrade and determine what went wrong.

What time were you trying to sell the stock? Before the open or after? If it was before, then you might need to specifically send a pre-market order via etrade. I don't use etrade but other brokers I do use have a separate trading interface for pre and post-market trading. Otherwise your post...

Based on the information OP gave, he was long the shares. You can sell at any price you want if you are already long, right?

Any sort of financial transaction tax would put me out of business overnight.

I'm not sure of the details but the exchanges (after the fact) busted all trades a certain % off the original prices before the flash crash. So I guess the people who placed those market or stop orders got a lucky break.

It happened during the flash crash, some equities traded at 1 cent and some traded at ridiculously high prints (can't recall the max). These were prints from market orders when market makers backed away to the lowest/highest possible bid/ask on individual equities (to comply with regulations...

Yes, the Annualized Income method is designed just for the type of irregular income stream that traders produce.

This is why they are called estimated taxes, because you won't know until the calendar year is over how much you will owe. If you pay too much, you'll get a refund but the IRS will get a little interest on that amount before they give it back. If you pay too little, you will pay penalties. In...

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I don't think that is correct. If you look at the applicable form(s), I believe you would need to pay 110% of your prior year tax burden in equal installments to avoid penalty.

Did your LLC make a mark-to-market election?

They don't always allow third party wires. I participated in a private placement successfully by wiring money from IB once. But then a couple of months later I tried it again and IB said they don't allow third party wires for private placements anymore. So I'm not sure what they allow and what...