Cross-Border Counselor
Benefits
Considerations for Awarding Incentive Stock Options
Canadian companies that award stock options to their employees, non‑employee directors and/or other service providers often inquire as to whether they should offer Incentive Stock Options (“ISOs”) to any such individuals who are U.S. taxpayers. Below is a discussion of some of the tax considerations in awarding ISOs and the main requirements that must be met for an option to qualify as an ISO. Please note, this blog post provides only a high‑level summary of the tax treatment of options as well as some of the notable requirements for an option to qualify as an ISO. This article does not purport to cover every nuance or situation. As such, you should consult with U.S. counsel (as well as your accountants) for assistance in determining whether ISOs should be awarded, and if so, the requirements that must be met. Tax Considerations in Awarding ISOs Under U.S. tax law, an option will be treated as either (i) an Incentive Stock Option or (ii) a Nonqualified Stock Option (“NSO”). An option that does not meet the requirements for ISO treatment will be treated as an NSO for tax purposes. An ISO allows the option holder the opportunity to obtain more favorable tax treatment in that (i) there is no tax due at exercise (as contrasted with NSOs where the spread is taxed at ordinary income rates at the time of exercise), and (ii) if ISO shares are held until the end or the required ISO holding period (i.e. held for at least one year after exercise and two years after grant), the excess of the sales price over the exercise price will be taxed at the long‑term capital gains rate. This means that the amount of the spread at the time of exercise is never taxed at the higher ordinary income rates and no Federal Insurance Contributions Act (“FICA”) taxes (i.e. Social Security and Medicare taxes) are paid. While there is the potential for more favorable tax treatment for the option holder, depending on the individual’s specific tax circumstances, the exercise of an ISO could trigger something known as alternative minimum tax, so the option holder may not actually get the full tax benefit. On the other hand, ISOs are potentially less favorable to the employer because it will not be eligible to take a compensation expense deduction on its U.S. corporate income tax return for the compensatory element of the ISO (i.e. the amount of the spread at the time of exercise), unless the employee makes a disqualifying disposition (i.e. sells before the end of the required ISO holding period). In contrast, the employer may take such deduction if the option is an NSO. What are the Requirements for ISOs? One of the main limitations of an ISO is that it may only be granted to employees of the issuing company (or a subsidiary). This means that non‑employee directors and consultants are not eligible to receive ISOs. Moreover, while it is common in Canadian equity plans for the number of authorized shares to be represented as a rolling percentage, a plan that awards ISOs must designate a fixed number of shares authorized to be granted as ISOs. An ISO may not have a term of longer than ten years, and there is no explicit exception to this rule for an ISO that may expire during a blackout. For each optionee, no more than $100,000 in options may first become exercisable in any calendar year, and to the extent the $100,000 limit is exceeded, the excess is treated as an NSO. Lastly, it is important to note that in order to grant ISOs, the plan must be approved by the shareholders of the issuing company within 12 months of adoption of the plan. Concluding Considerations It is worth reiterating that should an option designated as an ISO fail to meet any of the ISO requirements, the option will be treated as an NSO for tax purposes. As such, an option holder would be in no worse of a position than if the option had been originally designated as an NSO. For this reason, as long as shareholder approval is not expected to be an obstacle, many companies ultimately decide to award ISOs to employees that are U.S. taxpayers. In particular, companies that award options to lower‑to‑mid level paid employees may wish to consider ISOs, as these employees are not typically subject to the alternative minimum tax and would not likely exceed the $100,000 limit on ISOs.
December 23, 2024
Benefits
The Special Timing Rule for Taxation of Nonqualified Deferred Compensation
For an employee who is a U.S. taxpayer, both the employer and the employee are liable for a portion of Social Security taxes and Medicare taxes (collectively referred to as “FICA” taxes) on the employee’s compensation. Employers are liable for withholding and remitting both the employer and the employee portions of FICA taxes, which typically occurs at the time the compensation is received by the employee, which his known as the “General Timing Rule.” However, when dealing with awards of nonqualified deferred compensation (“NQDC”) to U.S. taxpayers, a Special Timing Rule (outlined in Treas. Reg. §31.3121(v)(2)-1) may apply. Under the Special Timing Rule, FICA taxes are owed when the employee becomes vested in the NQDC, whether or not the NQDC is actually paid at that time. If a Canadian company is unaware of this Special Timing Rule, it could result in the employer withholding and reporting incorrect FICA amounts as well as the employee overpaying FICA taxes. What is Nonqualified Deferred Compensation? A NQDC arrangement is really any kind of compensation that has been earned by an employee in one tax year, but that the employee will not receive until a later tax year. This could be as simple as a bonus earned in one year and payable in a later year, or as complex as equity-based awards, such as Restricted Stock Units, phantom stock, or a supplemental executive retirement plan (to name a few). However, this Special Timing Rule generally does not apply to stock options. What is the Special Timing Rule for FICA? As mentioned above, under the Special Timing Rule, FICA taxes are due on NQDC on the later of: (1) when the employee provides the related services, or (2) when the compensation is no longer subject to a substantial risk of forfeiture (i.e., when the amounts vest). In other words, FICA taxes could be due before the NQDC is actually paid to the employee. For a typical employer contribution-based cash plan or phantom stock plan, this rule means that FICA taxes will be due in the year when any deferred compensation (and any earnings) vest. This can become complex to track when there is an extended vesting schedule to ensure that the appropriate amount of FICA taxes are paid by the employer and employee when each tranche of the compensation (and earnings) vest. For a plan where employees are deferring salary or bonus, FICA taxes will be due in the year when the employee makes the deferral. To help ease some of the administrative complexity, there is a “rule of administrative convenience.” The rule allows FICA taxes to be withheld and remitted as late as December 31 of the same tax year, with the amount of wages subject to FICA adjusted to reflect the value on December 31 (or an earlier date if payment is made earlier) after interest or earnings on the benefit are applied. This rule can be helpful if amounts under a plan vest at numerous times during a year. There are additional rules that can be utilized to help manage this complex issue. What are the Consequences of not Complying with the Special Timing Rule? The Special Timing Rule, although a bit administratively complex, is typically advantageous to the recipient of the NQDC. If FICA taxes are paid when the NQDC vests (but is not paid out), then FICA taxes will not be owed when the NQDC is paid (to avoid double taxation). This generally means that any interest or accruals on the amounts that have already been subject to FICA taxes, will not be subject to FICA taxes at all. On the flip side, the Special Timing Rule can occasionally be disadvantageous if NQDC is never paid, as regulations do not allow employees to recover FICA taxes paid on NQDC amounts that are never received. Unfortunately, many employers forget, or are not aware of the requirement, to include NQDC in income for FICA tax purposes at the time of contribution or vesting. If FICA taxes are not paid in accordance with the Special Timing Rule, the issue may be corrected if caught in time to amend withholding returns; otherwise, FICA taxes are due when payments are actually (or constructively) received and become taxable for income tax purposes (likely resulting in more FICA taxes due overall). The correction process is complex, as it involves determining open tax years for which correction is available, amending prior returns and issuing corrected W-2s. Therefore, employers should be careful to understand their nonqualified deferred compensation plans, and how tax withholding works under those plans.
February 13, 2024
Benefits
Canadian Compensation Arrangements - When Do I Need U.S. Counsel?
Imagine a Canadian company adopts a deferred share unit plan (DSU Plan) for its directors. At the time the plan is adopted, the company does not have the plan reviewed by U.S. counsel, because none of their directors reside in the U.S. It is not until several years later that the company learns that one of its directors, despite living in Canada, has dual citizenship with the U.S. Because the typical form of Canadian DSU Plan will not comply with U.S. tax laws governing deferred compensation, particularly U.S. Internal Revenue Code Section 409A (Section 409A), the company has quite a mess on its hands. You can read our prior articles on common payment timing issues with DSUs here and common election deferral issues with DSUs here. It is because of scenarios like the above that it is crucial to consider whether any of your employees or non-employee directors are U.S. taxpayers. Unlike most other countries, U.S. taxpayers are taxed on worldwide income, regardless of where they reside. U.S. taxpayers include: (i) U.S. citizens regardless of residency; (ii) legal permanent residents (“green card” holders); and (iii) non-citizen, non-green card holders who have a “substantial presence” in the United States under the U.S. income tax laws (but exceptions to this category apply – careful analysis of the facts and applicable tax treaties is required). Section 409A is so broad that it covers most nonqualified deferred compensation arrangements, unless a specific exception applies, and it imposes specific timing, election and distribution requirements on covered arrangements. If a nonqualified deferred compensation arrangement fails to comply with the requirements of Section 409A, deferrals are includible in income at vesting (even if they are not paid out) and subject to a 20% additional tax. In some circumstances, an underpayment interest penalty will also apply. Because of the broad definition of Section 409A, it is easy to overlook that employment agreements, change-in-control agreements, and severance agreements with U.S. taxpayers frequently contain provisions that subject them to Section 409A. Because the failure to comply with Section 409A can result in such onerous tax penalties, if a Canadian company has U.S. taxpayers participating in its equity plans or if the company is entering into any type of compensation arrangement with a U.S. taxpayer where such arrangement promises to pay compensation in a future taxable year, the company should consider having the terms of any such plan or arrangement reviewed by U.S. counsel.
November 16, 2023
Benefits
DSU Plans May Run Afoul of U.S. Deferral Election Timing Rules Resulting in Adverse U.S. Tax Treatment
A Canadian company adopting a deferred share unit plan (DSU plan) for its directors must consider U.S. tax implications for U.S. taxpayers. It is important to remember that U.S. citizens and U.S. residents for tax purposes (including green card holders) are taxed on worldwide income, regardless of where they reside. As such, participation by a U.S. director, including an expat or holder of dual citizenship, could result in significant adverse tax consequences under Section 409A of the Internal Revenue Code, as a typical Canadian DSU plan often runs afoul of Section 409A. In a prior article, DSU Plans Require Careful Review to Avoid Adverse U.S. Tax Treatment, common payment timing violations of U.S. tax laws governing deferred compensation were discussed (as well as tips for properly identifying U.S. taxpayers). While payment timing is one common violation of Section 409A, it is also important to consider the timing of elections to defer compensation. In order to avoid a violation of U.S. deferral election timing rules, a Canadian company should consider both the general deferral election timing rules under Section 409A, as well as the exceptions permitting more lenient timing. Generally, deferral elections must be made by the end of the taxable year before the year in which the services giving rise to the compensation that will be deferred are performed. For instance, for any amounts earned in 2023, the election to defer should be made no later than December 31, 2022. Once a deferral election is made, payment may not be accelerated, unless a specific exception applies, and payment may not be further deferred, unless strict second deferral election rules are obeyed. While compliance with the general deferral election timing rule is always the simplest and least risky approach, there are exceptions to this general rule that provide greater leniency in some situations. One of the most common exceptions is for initial eligibility. Section 409A provides that a deferral election may be made within 30 days following the date that a service provider (e.g., a director) is first eligible to participate in the plan, provided that the election may only apply to compensation earned following the date of the election (and provided the service provider does not participate in another deferred compensation plan required to be aggregated with such plan under Code Section 409A). There are additional exceptions to the general deferral election timing rules for payments conditioned on continued service for a period of at least 12 months as well as for performance-based compensation. However, compliance with these exceptions can be rather tricky, and the consequences for failing to comply are severe, so these exceptions should be discussed with legal counsel proficient in U.S. tax law. Where a U.S. director fails to make a timely deferral election within the meaning of Section 409A, the value of the DSUs as of December 31st of the year in which the DSUs vest (i.e. the year in which the DSUs are awarded for the majority of DSU plans) will be included in the U.S. director’s income for that year, regardless of whether actual payment of the DSUs is deferred. In addition, a 20% penalty tax will be imposed on the U.S. director. Advanced planning is crucial to ensure compliance with the above-mentioned deferral election timing rules in order to avoid the adverse tax consequences described above. A Canadian company with U.S. directors should have any such DSU plan reviewed by counsel proficient in U.S. tax law prior to implementation. However, even where review prior to implementation is not possible, a review after implementation would still be advantageous, as early correction may avoid or minimize certain adverse tax consequences. We work regularly with Canadian tax counsel to ensure compliance and/or to correct violations.
November 7, 2022

