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@ixero@20, I dug some more and found some interesting case laws around this. To be honest, I haven't read through all of them yet but some food for thought for all. https://htkacademy.com/business-income-vs-capital-gains/ https://ummattaxlaw.ca/2019/05/21/are-you-earning-capital-gains-or-income/ https://decision.tcc-cci.gc.ca/tcc-cci/decisions/en/230346/1/document.do https://decision.tcc-cci.gc.ca/tcc-cci/decisions/en/item/26964/index.do https://decision.tcc-cci.gc.ca/tcc-cci/decisions/en/item/29032/index.do

@ixero@20, to be honest, I couldn't find anything online that would point me to any definitive guideline. The best I could find is this: https://taxinterpretations.com/node/393961 The same letter states that the courts will use a combinations of the factors listed above (from IT-479R). However, it does not indicate how many in combination will be taken into consideration. As stated previously, I was advised based on my situation where I fulfill a number of the factors, I would be better served to treat my income as business income than capital gains. This may or may not apply to you. I totally agree with @Kim here. It is not the fact that the holding was a short period of time (and it is unclear what is determined to be short). But rather say for example, there were many transactions, most or all of which were short term. The funds for the transactions were obtained through financing to purchase stocks and options in equities which are speculative in nature. The complexity of the transactions (various options strategies) would then also point to thorough understanding of securities markets. For someone that was trading in circumstances in this example, it would be likely looked at as business income. If in doubt, contact the tax professionals and sort out your personal situation.