COBRA Liabilities. Seller shall be responsible for providing notices and coverage under COBRA to any Plant Employee (and his or her qualified beneficiaries) as to whom a “qualifying event” (as defined in Section 4980B of the Code) has occurred on or prior to the Closing Date (including qualifying events that occur in connection with the transactions contemplated by this Agreement). Buyer shall be responsible for providing notices and coverage under COBRA to any Continuing Employee (and his or her qualified beneficiaries) whose “qualifying event” occurs after the Closing Date.

As of the Termination Date # the vested portion of each option award will be exercisable for 90 days thereafter, or any longer period specified in the Plan or the applicable option award agreement, subject to the maximum term applicable to such option, and the unvested portion of all option awards shall be forfeited to the Company, and # with respect to unvested restricted stock awards, all restrictions on unvested shares shall continue to lapse as if your termination had not occurred.

COBRA Health Benefit. Subject to the Company’s right of election for an alternative lump-sum payment under [Section 9(d)] hereof, if you are subject to an Involuntary Termination and you elect to continue your health insurance coverage under the Consolidated Omnibus Budget Reconciliation Act (“COBRA”) following your Separation, then the Company will pay the same portion of your monthly premium under COBRA as it pays for active employees and their eligible dependents until the earliest of # the close of the six (6) month period following your Separation, # the expiration of your continuation coverage under COBRA or # the date when you become eligible for substantially equivalent health insurance coverage in connection with new employment or self-employment.

Notwithstanding the foregoing, if at any time the Company determines, in its sole discretion, that it cannot pay the Company COBRA Payment without potentially incurring financial costs or penalties under applicable law (including, without limitation, Section 2716 of the Public Health Service Act), then regardless of whether Executive elects continued health coverage under COBRA, and in lieu of providing the Company COBRA Payment, the Company will instead pay Executive on the last day of each remaining month of the COBRA Payment Period, a fully taxable cash payment equal to the Company COBRA Payment for that month, subject to applicable tax withholdings (such amount, the “Special Severance Payment”), which payments shall continue until the earlier of expiration of the COBRA Payment Period or the date when Executive becomes eligible for substantially equivalent health insurance coverage in connection with new employment or self-employment.

Cash and COBRA Severance. The aggregate amount of the Cash and COBRA Severance (as defined in the Offer Letter) will be equal to Nine Hundred Thousand Dollars ($900,000), plus an amount equal to the cash bonus Employee otherwise would have received under [[Organization A:Organization]]’s fiscal year 2021 bonus plan in which Employee participated as of the Termination Date, based on # Employee’s target bonus opportunity of $865,000 for [[Organization A:Organization]]’s fiscal year 2021, and # actual performance for [[Organization A:Organization]]’s fiscal year 2021 compared to the applicable performance metrics set forth under such plan, but with such resulting amount prorated to reflect the portion of [[Organization A:Organization]]’s 2021 fiscal year during which Employee was an employee of the Company.

The Executive may continue coverage with respect to the Company’s group health plans as permitted by the Consolidated Omnibus Budget Reconciliation Act of 1985 (“COBRA”) for himself and each of his “Qualified Beneficiaries” as defined by COBRA (“COBRA Coverage”). The Company shall reimburse the amount of any COBRA premium paid for COBRA Coverage timely elected by and for the Executive and any Qualified Beneficiary of the Executive, and not otherwise reimbursed, during the period that ends on the earliest of # the date the Executive or the Qualified Beneficiary, as the case may be, ceases to be eligible for COBRA Coverage, # the last day of the consecutive eighteen (18) month period following the date of termination of the Executive’s employment and # the date the Executive or the Qualified Beneficiary, as the case may be, is covered by another group health plan. To reimburse any COBRA premium payment under this paragraph, the Company must receive documentation of the COBRA premium payment within ninety (90) days of its payment.

Additional Payment. An additional payment in the gross amount of $4,008.60, which is intended to cover the cost of COBRA premiums for Employee for six months (the “Additional Payment”). The Additional Payment will be paid to Employee in one lump sum, within 30 days from the Effective Date of this Agreement. Employee understands and acknowledges that it is Employee’s responsibility to timely elect COBRA overage and make all required COBRA payments directly to the applicable insurance carrier.

COBRA Benefits. “COBRA” as used herein shall mean the Consolidated Omnibus Budget Reconciliation Act of 1986, as amended. Executive shall receive a lump sum payment in an amount equal to the cost of COBRA continuation for a period of not less than twelve (12) months.

new employment or self-employment (such period from the termination date through the earliest of [(A) through (C)], the “COBRA Payment Period”). Notwithstanding the foregoing, if the Company determines, in its sole discretion, that the payment of the COBRA premiums could result in a violation of the nondiscrimination rules of Section 105(h)(2) of the Code or any statute or regulation of similar effect (including but not limited to the 2010 Patient Protection and Affordable Care Act, as amended by the 2010 Health Care and Education Reconciliation Act), then in lieu of providing the COBRA premiums, the Company, in its sole discretion, may elect to instead pay you on the first day of each month of the COBRA Payment Period, a fully taxable cash payment equal to the COBRA premiums for that month, subject to applicable tax withholdings (such amount, the “Special Severance Payment”), for the remainder of the COBRA Payment Period. You may, but are not obligated to, use such Special Severance Payment toward the cost of COBRA premiums. On the sixtieth (60th) day following your Separation from Service, the Company will make the first payment under this clause (and, in the case of the Special Severance Payment, such payment will be you, in a lump sum) equal to the aggregate amount of payments that the Company would have paid through such date had such payments commenced on the Separation from Service through such sixtieth (60th) day, with the balance of the payments paid thereafter on the schedule described above. If you become eligible for coverage under another employer’s group health plan or otherwise cease to be eligible for COBRA during the period provided in this clause, you must immediately notify the Company of such event, and all payments and obligations under this clause shall cease;

Rapid7 | 800 Boylston Street | Prudential Tower, 29th Floor | Boston, MA 02199 | www.rapid7.com nondiscrimination rules of Section 105(h)(2) of the Code or any statute or regulation of similar effect (including but not limited to the 2010 Patient Protection and Affordable Care Act, as amended by the 2010 Health Care and Education Reconciliation Act), and that payment of similar amounts on a taxable basis would not, then in lieu of providing the COBRA premiums, the Company will instead pay you on the last day of each remaining month of the COBRA Payment Period, a cash payment equal to the COBRA premiums for that month, subject to applicable tax withholdings (such amount, the “Special Severance Payment”), for the remainder of the COBRA Payment Period. The Company will also pay an additional payment on your behalf, directly to the applicable taxing authorities, (the “Gross-Up Payment”) at the time of each Special Severance Payment, in an amount equal to # the ordinary federal, state and local income and employment taxes due by you, if any, at that time (the “Taxes”) on the Special Severance Payment plus # an amount sufficient to cover the iterative Taxes on the Taxes. For clarity, this Gross-Up Payment is a full gross-up (that is, calculated ad infinitum) in the amount reasonably determined by the Company as necessary to put you in the same economic position as if you received the Special Severance Payment without incurring the Taxes. You agree to cooperate and provide ail necessary assistance and information to the Company to determine the amount of the Gross-Up Payment.