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Debt | 6 Months Ended
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Jun. 30, 2025
Debt Disclosure [Abstract] |
Debt | Note 10. Debt Convertible Senior Notes In May 2020, we issued $230.0 million aggregate principal amount of convertible senior notes due May 1, 2025 (the “2025 Notes”), in March 2021, we issued $600.0 million aggregate principal amount of convertible senior notes due March 15, 2027 (the “2027 Notes”), and in September 2023, we issued $300.0 million aggregate principal amount of convertible senior notes due March 15, 2029 (the “2029 Notes”) (collectively, the “Notes”). In September 2023, we used $201.0 million of the proceeds from the issuance of the 2029 Notes to repurchase and retire $184.0 million aggregate principal amount of the 2025 Notes and paid accrued and unpaid interest thereon. Further details of the Notes are as follows:
Issuance |  | Maturity Date |  | Interest Rate |  | First Interest Payment Date |  | Effective Interest Rate |  | Semi-Annual Interest Payment Dates |  | Initial Conversion Rate per $1,000 Principal |  | Initial Conversion Price |  | Number of Shares (in millions)
2025 Notes |  | May 1, 2025 |  | 2.25% |  | November 1, 2020 |  | 2.88% |  | May 1 and November 1 |  | 16.3875 |  | $ | 61.02 |  |  | 0.8
2027 Notes |  | March 15, 2027 |  | 0.25% |  | September 15, 2021 |  | 0.67% |  | March 15 and September 15 |  | 9.6734 |  | $ | 103.38 |  |  | 5.8
2029 Notes |  | March 15, 2029 |  | 1.25% |  | March 15, 2024 |  | 1.69% |  | March 15 and September 15 |  | 15.4213 |  | $ | 64.85 |  |  | 4.6
On May 1, 2025, the Company paid $46.5 million to redeem the outstanding portion of the 2025 Notes, including the outstanding principal amount and accrued interest through the maturity date of the 2025 Notes. The 2027 Notes and the 2029 Notes are senior unsecured obligations, do not contain any financial covenants and are governed by indentures between the Company, as issuer, and U.S. Trust Company, Bank National Association, as trustee (the “Indentures”). The total net proceeds from the 2025 Notes, the 2027 Notes and the 2029 Notes offerings, after deducting initial purchase discounts and debt issuance costs, were $222.8 million, $585.0 million and $292.0 million, respectively. As of June 30, 2025, the 2027 Notes and the 2029 Notes were not convertible at the option of the holders. The holders may convert the 2027 Notes and the 2029 Notes at any time on or after December 15, 2026 and December 15, 2028, respectively, until the close of business on the second scheduled trading day immediately preceding the maturity date, regardless of the circumstances set forth above. Upon conversion, we will pay or deliver, as the case may be, cash, shares of our common stock or a combination of cash and shares of our common stock, at our election, in the manner and subject to the terms and conditions provided in the Indentures. If we undergo a fundamental change (as set forth in the Indentures) at any time prior to the maturity date, holders of the Notes will have the right, at their option, to require us to repurchase for cash all or any portion of their Notes at a repurchase price equal to 100% of the principal amount of the Notes to be repurchased, plus accrued and unpaid interest to, but excluding, the fundamental change repurchase date. In addition, following certain corporate events that occur prior to the maturity date or following our issuance of a notice of redemption, in each case as described in the Indentures, we will increase the conversion rate for a holder of the Notes who elects to convert its Notes in connection with such a corporate event or during the related redemption period in certain circumstances. For additional details on the terms of our Notes, see Note 11, Debt, to the consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024. Accounting for the Notes In accounting for the issuance of the Notes, the principal less debt issuance costs are recorded as debt on our unaudited condensed consolidated balance sheet. The debt issuance costs are amortized to interest expense using the effective interest method over the contractual term of the Notes. The net carrying amount of the Notes as of June 30, 2025 and December 31, 2024 was as follows (in thousands):
|  | 2025 Notes |  | 2027 Notes |  | 2029 Notes
|  | Principal |  | Unamortized debt issuance costs |  | Total |  | Principal |  | Unamortized debt issuance costs |  | Total |  | Principal |  | Unamortized debt issuance costs |  | Total
Balance at December 31, 2024 |  | $ | 45,992 |  |  | $ | (97) |  |  | $ | 45,895 |  |  | $ | 600,000 |  |  | $ | (5,564) |  |  | $ | 594,436 |  |  | $ | 300,000 |  |  | $ | (6,080) |  |  | $ | 293,920 |
Amortization of debt issuance costs |  | — |  |  | 97 |  |  | 97 |  |  | — |  |  | 1,241 |  |  | 1,241 |  |  | — |  |  | 680 |  |  | 680 |
Principal payment upon maturity |  | (45,992) |  |  | — |  |  | (45,992) |  |  | — |  |  | — |  |  | — |  |  | — |  |  | — |  |  | — |
Balance at June 30, 2025 |  | $ | — |  |  | $ | — |  |  | $ | — |  |  | $ | 600,000 |  |  | $ | (4,323) |  |  | $ | 595,677 |  |  | $ | 300,000 |  |  | $ | (5,400) |  |  | $ | 294,600 |
Interest expense related to the Notes was as follows (in thousands):
| Three Months Ended June 30,
| 2025 |  | 2024 |  |
| 2025 Notes |  | 2027 Notes |  | 2029 Notes |  | Total |  | 2025 Notes |  | 2027 Notes |  | 2029 Notes | Total |  |  |  |  |  |  |
Contractual interest expense | $ | 86 |  |  | $ | 375 |  |  | $ | 938 |  |  | $ | 1,399 |  |  | $ | 259 |  |  | $ | 375 |  |  | $ | 937 |  | $ | 1,571 |  |  |  |  |  |  |  |
Amortization of debt issuance costs | 24 |  |  | 627 |  |  | 348 |  |  | 999 |  |  | 73 |  |  | 624 |  |  | 311 |  | 1,008 |  |  |  |  |  |  |  |
Total interest expense | $ | 110 |  |  | $ | 1,002 |  |  | $ | 1,286 |  |  | $ | 2,398 |  |  | $ | 332 |  |  | $ | 999 |  |  | $ | 1,248 |  | $ | 2,579 |  |  |  |  |  |  |  |
| Six Months Ended June 30,
| 2025 |  | 2024 |  |
| 2025 Notes |  | 2027 Notes |  | 2029 Notes |  | Total |  | 2025 Notes |  | 2027 Notes |  | 2029 Notes | Total |  |  |  |  |  |  |
Contractual interest expense | $ | 345 |  |  | $ | 750 |  |  | $ | 1,875 |  |  | $ | 2,970 |  |  | $ | 518 |  |  | $ | 750 |  |  | $ | 1,874 |  | $ | 3,142 |  |  |  |  |  |  |  |
Amortization of debt issuance costs | 97 |  |  | 1,241 |  |  | 680 |  |  | 2,018 |  |  | 149 |  |  | 1,247 |  |  | 622 |  | 2,018 |  |  |  |  |  |  |  |
Total interest expense | $ | 442 |  |  | $ | 1,991 |  |  | $ | 2,555 |  |  | $ | 4,988 |  |  | $ | 667 |  |  | $ | 1,997 |  |  | $ | 2,496 |  | $ | 5,160 |  |  |  |  |  |  |  |
Capped Calls In connection with the offering of the 2025 Notes, the 2027 Notes and the 2029 Notes, we entered into privately negotiated capped call transactions with certain counterparties (the “2025 Capped Calls”, “2027 Capped Calls” and “2029 Capped Calls”) (collectively, the “Capped Calls”). The Capped Calls are expected to reduce potential dilution to our common stock upon conversion of a given series of notes and/or offset any cash payments that we are required to make in excess of the principal amount of converted notes of such series, as the case may be, with such reduction and/or offset subject to a cap. The Capped Calls are subject to adjustment upon the occurrence of certain specified extraordinary events affecting us, including merger events, tender offers and announcement events. In addition, the Capped Calls are subject to certain specified additional disruption events that may give rise to a termination of the Capped Calls, including nationalization, insolvency or delisting, changes in law, failures to deliver, insolvency filings and hedging disruptions. The following table sets forth other key terms and premiums paid for the Capped Calls related to each series of Notes:
|  | Capped Calls Entered into in Connection with the Issuance of the 2025 Notes |  | Capped Calls Entered into in Connection with the Issuance of the 2027 Notes |  | Capped Calls Entered into in Connection with the Issuance of the 2029 Notes
Initial strike price, subject to certain adjustments |  | $ | 61.02 |  |  | $ | 103.38 |  |  | $ | 64.85 |
Cap price, subject to certain adjustments |  | $ | 93.88 |  |  | $ | 159.04 |  |  | $ | 97.88 |
Total premium paid (in thousands) |  | $ | 27,255 |  |  | $ | 76,020 |  |  | $ | 36,570 |
Expiration dates |  | March 4, 2025 - April 29, 2025 |  | January 1, 2027 - March 11, 2027 |  | February 13, 2029 - March 13, 2029
The 2025 Capped Calls expired in full on April 29, 2025. The Company did not elect to exercise any portion of the 2025 Capped Calls prior to expiration. For additional details on the terms of our Capped Calls, see Note 11, Debt, to the consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024. For accounting purposes, the 2025 Capped Calls, the 2027 Capped Calls and the 2029 Capped Calls are separate transactions, and not part of the terms of the 2025 Notes, the 2027 Notes and the 2029 Notes. The 2025 Capped Calls, 2027 Capped Calls and 2029 Capped Calls are recorded in stockholders' equity and are not accounted for as derivatives. Credit Agreement On June 25, 2025 (the "Closing Date"), the Company entered into a credit agreement (the "Credit Agreement"), by and among the Company, Rapid7 LLC, the lenders party thereto and JPMorgan Chase Bank, N.A., as administrative agent, that provides for a $200.0 million revolving credit facility with a letter of credit sublimit of $20.0 million. The Credit Agreement allows for incremental facilities up to the greater of $141 million or 75% of Consolidated EBITDA (as defined in the Credit Agreement). Additional incremental facilities may be incurred, subject to certain conditions. We incurred fees of $1.6 million in connection with entering into the Credit Agreement. The fees are recorded in other current and non-current assets on the consolidated balance sheet and are amortized on a straight-line basis over the contractual term of the arrangement. Under the terms of the Credit Agreement, we are required to pay a commitment fee on the unused portion of the credit facility. The commitment fee rate is determined by the total net leverage ratio of the Company and its subsidiaries, ranging from 0.20% to 0.25% per annum on the unused portion of the credit facility. The commitment fee is expensed as incurred and included within interest expense on the condensed consolidated statement of operations. The Credit Agreement matures on the fifth anniversary of the Closing Date or, if certain specified liquidity conditions are not satisfied, 91 days prior to the earliest maturity date of either the 2027 or the 2029 Notes. The Credit Agreement also contains certain affirmative and negative covenants, including a requirement to maintain a minimum interest coverage ratio for the duration of the Credit Agreement and a maximum net leverage ratio. The borrowings under the Credit Agreement bear interest at a variable annual rate based on either the Secured Overnight Financing Rate (SOFR) subject to a floor of zero or alternate base rate plus, in each case, a fixed margin, which varies depending on the Company’s net leverage ratio. As of June 30, 2025, we did not have any outstanding borrowings under the Credit Agreement. As of June 30, 2025, we had a total of $6.0 million in letters of credit outstanding as collateral for certain office space leases which reduce the amount of borrowing availability under our Credit Agreement.

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