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We'd recommend maximizing your ESPP sometimes even before maximizing your 401(k). The percentage will vary, but you'll want to maximize your ESPP contributions however you can. Note: If you have the ability to max out an HSA or Roth IRA, those should be priorities as well.
The IRS limits purchases under a Section 423 plan to $25,000 worth of stock value (based on the grant date fair market value) for each calendar year in which the offering period is effective.
An ESPP must be approved by the stockholders of the sponsoring corporation within the period commencing 12 months before and ending 12 months after the ESPP is adopted by the sponsoring corporation's board of directors.
In this situation, you sell your ESPP shares more than one year after purchasing them, but less than two years after the offering date. This is a disqualifying disposition because you sold the stock less than two years after the offering (grant) date.
However, there is a limit on ESPP maximum contribution. Under a Section 423 plan, the IRS limits purchases to $25,000 worth of stock value (based on the FMV on the offering date) for each calendar year.
If your company offers a tax-qualified ESPP and you decide to participate, the IRS will only allow you to purchase a maximum of $25,000 worth of stock in a calendar year. Any contributions that exceed this amount are refunded back to you by your company.