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ESPPs · Case studies

Illustrative scenarios, start to finish.

Same plan, same employee. One year she sold at purchase. The next year she held for the tax break. Here is which one came out ahead.

One filer almost paid tax twice on the same discount. The fix was one number on one form, and it saved him about $4,000.

He held for the lower tax rate and watched the stock fall 60% before the clock ran out. The tax break saved a little. The hold cost a lot.

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