I was wondering if anyone has experience with an ESOP and NUA tax treatments? I am retiring in early August after 36+ years. We are an employee owned company and I have a large amount of stock. We are an S-corp and nearly 100% of the shares are held by the employees in an ESOT. We have done well over the years so my share prices have appreciated a great deal over that time. I will receive my payout over a 10 year period, this year being the first distribution later in the year after I'm gone. I want to claim an NUA on the shares that I sell each year and pay the LTCG tax rate. I think the way I plan to take the money it would save a lot in taxes. The ESOP is telling me that to claim the NUA as a capital gains I have to get a lump sum distribution and that's not going to happen. Anyone familiar with this situation? I know its fairly unusual. We also have some disagreement on how the share basis is calculated.