{ "media_type": "text", "post_content": "If I sold a Jan 22 covered call that is now in the money would it make sense to roll it a few days before the last ex date (Nov) before the strike date to reduce the possibility of it being exercised early? I bought the stock in December 2020 so I'd rather keep it until I get LT treatment and if my understanding is correct I could generate a 2021 capital loss on the covered call then recognize the LTCG on the stock in 2022 (plus or minus the rolled option gain/loss).", "post_id": "60f7380e2d57e000203b1804", "reply_count": 3, "vote_count": 1, "bowl_id": "5acc42208c6b52001375e11e", "bowl_name": "Option Traders & Investing" }

If I sold a Jan 22 covered call that is now in the money would it make sense to roll it a few days before the last ex date (Nov) before the strike date to reduce the possibility of it being exercised early? I bought the stock in December 2020 so I'd rather keep it until I get LT treatment and if my understanding is correct I could generate a 2021 capital loss on the covered call then recognize the LTCG on the stock in 2022 (plus or minus the rolled option gain/loss).

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What you said about gain/loss is basically right. One caveat is that STCL is capped at $3k per year. Although in regards to ‘reducing the possibility of exercising early’, this is probably true if your option expires very soon with minimal time value. Technically even you roll your option, the long side can still exercise the newly opened one. I’ve seen my covered call get exercised one or two weeks ahead, not any much more advance. This could depend on the underlying stock though.

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Yes - once your underlying becomes LT, you’ll start enjoying the flexibility of keep rolling these CCs or release the capital.

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