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Let's say I want to create a good-til-canceled limit order to buy 100 shares of DAL at $35, but I don't want to indefinitely tie up $3500 in cash. Instead when the DAL limit is reached, I'd like to sell enough ITOT to buy the DAL shares.

Is there any way to express this to Fidelity or Schwab in the form of a conditional order? Note that I would be OK having to approximate the number of ITOT shares when I created the order if that made it possible.

It seems like I want some sort of weird One-Triggers-Another conditional order, that may not be possible because the execution would be backwards (I can't buy before I sell).

Thanks for your expertise!

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See if a Basket Order with a limit condition does the trick, assuming that Fidelity and Schwab offer such an order.

Another possible approach would be see if they offer Stock-Stock combination orders which is the same construct as an options spread (long one leg and short the other). You'd go long DAL and short ITOT in a ratio if you wish to do it for no cash outlay. The problem with such an order is that the ratio will change day to day due to the change in price of the components so you'll have to constantly adjust the order.

Why would it be a problem if the execution is backwards ("I can't buy before I sell")? Is it because you don't have approval for shorting and you are selling ITOT shares that you own?

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  • Thanks for your response! Looks like at least Fidelity does not offer limit basket orders. For the last question, correct I own ITOT in a non-margin account. So the solution might be to enable margin trading so I could have an OTA order where I limit-buy DAL which triggers a market-sell of my ITOT, using margin to cover the DAL cost until the ITOT proceeds are available?
    – Desmondo
    Mar 6, 2020 at 15:37
  • @Desmondo - Yes, you would need a margin account because the funds from the sale of your ITOT shares would not be available until T+2. If you care about the fill price on ITOT when DAL hits $35 then I would not use any of these conditional orders. Assuming that you are not tied up elsewhere (employment?), just set a price alert when DAL gets to say $36, reevaluate and if it looks acceptable, place the order. Mar 6, 2020 at 17:10

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