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Answers
I authored a 30 pageaccounting guide for my last employer who issued and redeemed stock options under their Share Based Compensation plan.
It might be helpful to know what type of plan you are administrating, there are so many.
Assuming a par value of $1, I would record the net settlement (#1) as follows:
APIC dr 2,060
Common Stk (60 shs times $1) cr 60
Payroll Taxes Payable ($5K gross comp times tax rate) cr 2,000
Anyone else agree?