UPDATE: TD Ameritrade has said it is now working to correct the issue discussed in this article and has promised a price correction on this particular order.  They said that the complaint went to the wrong department due in part to the restructuring of the company related to the merger between Thinkorswim and TD Ameritrade.

As a seasoned investor, I have developed many habits.  One of them has been sticking with my original retail broker, TD Ameritrade (TD Ameritrade Holding Corp: AMTD).  I have put up with a lot of their system’s quirks and I am presenting a recent example for those who are shopping for professional online brokers:

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I was assigned 98,100 shares short of Citigroup from an option position I took on the previous day.  In the morning I was asked to buy back the assigned short position by near the end of the business trading day because Ameritrade could not locate shares to borrow. No problem, I had done this successfully several times before.

That same morning, I put in an order to buy back 40,000 shares of Citigroup and it executed without any issue.  I also called to discuss my margin requirements and to get a better understanding of what I could do after I closed out the rest of the short position, given my account value.

I found an ideal moment to take care of the rest of the short position and I put in an order at 1:55 19 seconds CST to buy 58,100 shares of Citigroup at the asking price of $3.06.

Wait, what?  The order was rejected…