I'm looking to pay estimated quarterly taxes. Do wash-sale rules apply to quarterly estimated tax payments (June 1st – August 31st with a due date of September 15th for this past period), or do they only apply when filing my completed year-end returns next year?
For example, I have multiple large realized short-term gains AND losses in options with the same underlying stock occurring around the end of August and early September. I'm interpreting this rule in one of two ways, but perhaps they're both wrong and I'm misinterpreting this greatly:
- The wash sale rule is applied to quarterly payments. For this past period's estimated taxes, I need to make estimated tax payments on realized gains with a closing date on or before August 31st. For losses, I am unable to claim the realized losses from August because I bought options with the same underlying in early September. Even if I were to liquidate all my positions right now, I would not be able to claim these losses as they would be forwarded into the cost basis of these positions.
- The wash sale rule is only applicable to the tax year as a whole. I only need to make estimated tax payments based on my net realized gain/loss related to this stock as of end-of-day August 31st. As long as I plan to fully liquidate all my positions related to this stock by end of year and refrain from buying back a related position for 30 days, I will be able to claim realized losses as expected when I file my 2020 returns next year.
Some people have advised on simply overpaying taxes just to cover myself, but this is something I'd like to avoid as my realized capital gains and losses are both large, making my net gain relatively small. My tax burden would be much higher than my net gain. I've sent my questions to two different CPAs but they have been terribly slow at responding, so I'm looking for other people's experience in the meantime.