Back in the day, when I had a decent ESPP, I learned from experience to SELL and SELL immediately. In the final few years I would even sell short a few days before the distribution so as to hedge my position. Some people got burned by delays in having their accounts credited; meanwhile the stock tanked and they lost out.

Holding out for LTCG treatment is a fools errand if the stock is too risky an investment.

SELL SELL SELL. You’ve already invested you life there; time to diversify.