I recently left my position at a publicly traded company after 10+ years where I had an ESOP Retirement plan. That plan appears to have used an average cost basis versus basis on individual tax lots throughout the years.

I’ve had all company stock from that account distributed in kind to a taxable investment account and the remainder – cash – rolled over into an IRA. The distribution was initiated after Jan 1, 2020.

I understand:

1) I need to pay income tax on the cost basis component of that company stock (roughly 30-35% total value) as well as a 10% penalty (I’m under 59 1/2)

2) the NUA portion (roughly currently 65-70% of total value) is taxed at the Long Term Captital Gains rate

3) Any further appreciation since distribution is taxed as normal income

I have a couple questions regarding logistics of the tax liabilities.

When is the tax on the cost basis portion – ordinary income – and early withdrawal penalty due? Immediately, at quarter end, end of 2020 Tax Year? Via what form?

Assuming no further appreciation and after liquidating say the exact cost basis amount, how do I report that I owe no further taxes on that amount (since it was paid as normal income tax)?

Assuming future appreciation – say 5% – and liquidation beyond the cost basis amount how do I itemize the 2 components of that tax liability? Long Term Capital Gains on the amount liquidated plus normal income tax on the amount it appreciated post distribution.

I have 2 other accounts accumulated under that employer – a 401K (both Traditional and Roth components within) and a Qualified Profit Sharing Plan. Neither hold company stock directly. Do these fall under “like” plans that require distribution as well? I don’t believe the do but?

Thank you!

John