Law or statutes don't define this exactly. You will be OK as long as you aren't under any audit. If under an audit it depends on amount involved and if the other side represents someone who really wants to take an opposing view or not. These things aren't defined clearly so a moron can argue to his advantage. There is also a subtle underline in wash sale rule that it spans brokerage accounts and tax deferred accounts too but irs does not get basis from tax deferred accounts. What is the probability that the software would include pairs of tickers to catch them?If one is long a bear index fund like SDS (s&p short etf) and you short an etf like SPY does a wash sale come into play ?