ESPP with 1 month offering period, sell every month?

USA Discussion in 'General Accountancy Discussion' started by jdguay, Feb 13, 2019 at 7:40 PM.

  1. jdguay


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    My company has been offering an ESPP for quite few years. I enrolled when program was first offered and have been participating ever since.

    I tried researching ESPP's when I enrolled and most online resources recommended selling the stocks immediately after purchase. This seemed crazy to me, mainly because my company's offering period is only one month. (I am thinking this might be intentional to help prevent immediate sales) Monthly I am only purchasing maybe $100 to $200 of stock.

    Needless to say, I never sold the stock until I had an expenses I needed to cover. Well last year was a bad year and I sold stock 4 times. Not the entire number of stocks, I still have some 60 shares currently trading around $54. With the down market I knew I was selling at a loss, so I thought the loss would offset gains come tax time. Now I am entering the 1099-B and I noticed this "wash sale disallowed" column. Researched that and yup, because the offering period is every 30 days, there is no way to avoid wash sale violations. Unless I stop the purchase before I make the sale, wait 60 days then restart.

    Finally my question, should I sell the remaining holdings, then sell the little amount each month that I purchase? Take the 15% and run?

    Any advice?
    jdguay, Feb 13, 2019 at 7:40 PM
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