In its ruling of 1 December 2025, No. 299, the Italian Revenue Agency provided clarification regarding abuse of law in connection with \u201cone-coupon\u201d bonds where there is a timing mismatch between the issuer\u2019s deduction of interest expense and the taxation of interest income for investors.<\/p>\n
The Agency held that there is no abusive tax advantage<\/strong>: although the issuer deducts interest on an accrual basis and the investors are taxed on a cash basis, the resulting mismatch does not constitute an undue tax benefit. Since the first condition of Article 10-bis of Law 212\/2000 (undue tax advantage) is not met, the anti-abuse analysis does not proceed to the other requirements.<\/p>\n In the case at hand, the company intends to finance major investments through a subordinated, unsecured bond loan with a 15\u201320-year horizon, offered to shareholders, directors, employees, and third parties.<\/p>\n The bonds are \u201cone coupon\u201d instruments (a single payment at maturity) with a compounded annual rate of up to 16.5%. Tax is withheld upon payment of the interest, while the issuer deducts interest on an accrual basis. This creates the timing mismatch addressed in the ruling.<\/p>\n In this case, the transaction finances strategic investments and the timing mismatch is inherent to \u201cone-coupon\u201d structures. It is not contrary to the fiscal system\u2019s purposes.<\/p>\n","protected":false},"excerpt":{"rendered":" In its ruling of 1 December 2025, No. 299, the Italian Revenue Agency provided clarification regarding abuse of law in connection with \u201cone-coupon\u201d bonds where there is a timing mismatch between the issuer\u2019s deduction of interest expense and the taxation of interest income for investors. The Agency held that there is no abusive tax advantage: […]<\/p>\n","protected":false},"author":3,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"inline_featured_image":false,"footnotes":""},"categories":[1],"tags":[],"class_list":["post-3282","post","type-post","status-publish","format-standard","hentry","category-unkategorisiert"],"yoast_head":"\n