457 Special Catch-Up Deferrals

Another catch-up tool available to 457 plan participants is the 457 special catch-up deferral. This allows plan participants who are three years away from attaining normal retirement age in their 457 plan to defer: 

• Twice the yearly limit on deferrals ($37,000 in 2018, which is two times the yearly maximum contribution of $18,500 in 2018) for the three years leading up to normal retirement age; or  

• The yearly limit on deferrals plus any amount allowed in prior years that you chose not to or could not contribute. Plans will keep an ongoing list of amounts you were allowed to defer in prior years, the amount you actually deferred, and any shortfall from those years. If you choose this option, they add up all your shortfall and allow you to contribute an amount equal to the shortfall over the next three years. 

For governmental 457 plans, this additional contribution cannot be paired with the over-50 catch-up, which makes it important to use the one that will provide you with the greatest benefit or largest contribution. 

15-Year 403(b) Catch-Up Deferrals

There may be a special provision in a 403(b) plan that allows an additional catch-up separate from the over-50 catch-up. The additional catch-up, which amounts to $3,000 per year, is available to employees who have provided the same employer with 15 years of service. The amount of the allowable 15-year catch-up deferral is calculated as the lesser of: 

• $3,000; or 
• $15,000 reduced by all prior 15-year catch-up deferrals; or 
• $5,000 x years of service, reduced by all prior elective deferrals (including all past 15-year catch-up deferrals) to your 401(k)s, 403(b)s, SARSEPs, or SIMPLE IRAs sustained by your employer. 

For employees who are eligible for the 15-year catch-up deferral and the over-50 catch-up, the 15-year catch-up deferral should generally be used first; the over-50 catch-up falls second in priority.

Optimizing Taxes: Backdoor Roth IRA Contributions

This unique strategy becomes available if your 401(k) plan allows you to roll over an IRA account into the 401(k) plan. Normally, single people making over $120,000 a year and married people filing taxes jointly making over $189,000 a year are limited in their ability to contribute to a Roth IRA (the income numbers are based on your Modified Adjusted Gross Income). By using the backdoor Roth IRA strategy, a highly compensated individual can contribute to a non-deductible IRA and convert it to a Roth IRA. The problem is that any Roth conversions must be done pro-rata across all IRA accounts. This means that, if you have a deductible IRA in addition to a non-deductible IRA being funded, any conversion of IRA money would be taken from both pre- and post-tax IRA accounts pro-rata. This creates a tax on the distributions from the deductible IRA where otherwise there would be none. 

To avoid this additional taxation, you could potentially transfer the deductible IRA money into your 401(k) and then convert the new non-deductible IRA contributions to a Roth IRA without creating a taxable distribution.

Potential Downsides for Company Stock in a 401(k)

All tax strategies can be useful, but it is generally not recommendable to let the “tax tail wag the dog.” Trying to pursue this NUA strategy too aggressively can lead to you owning too much company stock and not having your portfolio appropriately diversified. You only have a few different triggering events, which means you only have a few opportunities to distribute the stock, possibly leading to overzealous distributions in the year in which they can be made. This can lead to paying taxes at a higher-than-normal tax bracket and not leaving as much money as you would normally leave in your retirement account, ultimately leading to higher taxes in the long run because all the investments held outside your retirement account are taxed every year. Your heirs do not receive a “step up in basis” on NUA shares upon your passing. You may be charged a penalty for an early retirement account withdrawal if you retire earlier than 59.5 years old, (although in some cases you can take penalty-free distributions as early as age 55). You cannot strategically convert these assets into Roth IRA assets over the years at a potentially low tax rate if they are taken as NUA; however, any amounts rolled into an IRA and not taken as an NUA distribution can still be converted to a Roth IRA. You will have to pay any applicable state taxes on the NUA withdrawal, which may apply equally to ordinary income and capital gains.

Keep in Mind 

• You will have to pay gains (for any price changes in the stock subsequent to the distribution) on any shares distributed from the retirement account and not sold immediately as either short- or long-term gains. 

• It is generally wise to keep the NUA stock in an account separate from other company stock to simplify your recordkeeping.  

• In addition, note that the NUA is not subject to the 3.8% Medicare surtax on net investment income. 

• You are allowed to “cherry pick” which shares of stock to distribute in kind to the brokerage account and roll the remainder into an IRA. 

• Your heirs are allowed to take an NUA distribution when you pass away if the shares are still held in the company plan. 

• If you separate from service before the age of 59.5, have a very highly appreciated employer stock position, and you need to make a distribution from your retirement account, you would have to pay the normal 10% early withdrawal penalty. However, the penalty will be calculated off of your cost basis. This means if you purchased shares for $1,000 that are now worth $50,000, you can withdraw the $50,000 in employer stock and only pay the ordinary taxes and 10% penalty on the $1,000 cost basis. Then you would only have to pay taxes on the remaining $49,000 at your current capital gains tax rate. 

• You may be able to take an NUA distribution and then strategically sell the shares off in small amounts over the years to keep your income limited to a level that allows for 0% capital gains rates. 

• You can use the NUA distribution to satisfy your first required minimum distribution if you are over the age of 70.5 when you retire so you only have to pay ordinary income taxes on a potentially low-cost basis amount rather than the full amount of your first distribution when you would have had to distribute money from your retirement account anyway. This can significantly reduce the taxes due on your first required minimum distribution.

Company Stock in a 401(k): Net Unrealized Appreciation

Net Unrealized Appreciation (NUA) is the name of a little-known tax break that can help save you money on taxes from employer stock held in a 401(k) plan if you qualify. NUA rules allow you to take employer stock out of your 401(k) upon certain triggering events, only pay ordinary income taxes on the cost basis of the stock (the price you originally paid for the stock) for the withdrawal, and then have the gains taxed at capital gains tax rates. This can be particularly valuable if: 

• You have highly appreciated employer stock (stock with very low-cost basis);  
• You have an immediate need to withdraw money from your 401(k);  
• You are retiring after age 70.5 and you have to take your first required minimum distribution (RMD); or  
• You have a short RMD period, including stretch RMDs. 

The rules for an NUA distribution are very strict, and you should work with your CPA to make sure you follow all the rules precisely. The rules are as follows: 

• You have to distribute the entire balance of your 401(k) and any other qualified plans you have with the employer in a single tax year (some can be withdrawn directly to a taxable account and some can be rolled into an IRA, but there can be no money left in your 401(k) account at the end of the tax year).  
• You must take the distribution of company stock from your 401(k) in actual shares—you cannot sell the shares in the 401(k) and then distribute cash.  
• You must have experienced one of the following triggering events: 
• Separation from service from the company whose plan holds the stock (this may include certain cash buyouts of the company you work for);  
• Reached age 59.5; 
• Become disabled; or 
• Death 

Mega Backdoor Roth 401(k) contributions

By using the right strategies, you may be able to contribute more than you thought possible and, in turn, save more money on taxes over time. In general, employees can only contribute up to $18,500 per year to a retirement plan with an additional catch-up of up to $6,000 per year if the employee is 50 years old or older (“employee contribution limit”). Many employees don’t realize that the maximum contribution to one of these accounts is $55,000 per year plus the catch-up (“maximum contribution limit”)—and that they may be able to contribute up to that amount despite the employee contribution limit and employer matching amounts adding up to less than the full maximum contribution limit.

The strategy is as follows:

Normally, this would mean you could not fund your 401(k) up to the maximum contribution limit of $55,000, leaving a full $24,000 on the table ($55,000 – $31,000 = $24,000). If you have a nondeductible 401(k) and work for a company with retirement plan documents that allow it, however, you can make a $24,000 contribution to the nondeductible part of the 401(k) and then convert the contribution to the Roth portion of your 401(k). This effectively allows you to maximize the yearly contribution to your retirement account. 

A very highly compensated employee can still take advantage of this strategy because employers can only base 401(k) matching off $275,000 of an employee’s compensation per year no matter how highly compensated the individual is. A 401(k) can provide a versatile savings account by allowing penalty-free (but not tax-free) distributions of certain amounts for a down payment on a home purchase or medical expenses. Keep in mind that any additional profit-sharing plan contributions by the employer must be considered when calculating the overall yearly contribution. It is very important to check the plan documents and speak with your HR department or plan administrator to make sure you are getting the most from your retirement plan.