Hypervalent iodine reagents are now well-established for the functionalization of nucleophiles under mild conditions due to their unique reactivity. 1 More recently, they have been also successful in the functionalization of radicals. In particular, ethynylbenziodoxolone (EBX) reagents have emerged as excellent radical traps, enabling the synthesis of alkynes otherwise difficult to access (Scheme 1A). 2 Efficient access toward structurally diverse alkynes is urgently needed, due to their numerous applications in synthetic and medicinal chemistry, chemical biology and organic materials. 3 The combination of visible-light photocatalysis and EBX reagents has been especially successful, allowing new processes, such as decarboxylative 4 or deoxygenative alkynylations, 5 as well as alkene 6 and C-H functionalization. 7 In contrast, the direct alkynylation of inert C-C bonds is more challenging. The use of the ring strain of cyclopropanes is wellestablished in synthetic chemistry to enable C-C bond cleavage. First applied to more reactive Donor-Acceptor systems, 8 less reactive Donor-only arylcyclopropanes could be also recently functionalized through oxidative activation to give radical cations (Scheme 1B). 9 Photocatalytic methods have further led to new multi-functionalization reactions. 10 However, concerning alkynylation, success has been limited for a long time to cyclopropanols, giving access only to ketones as products. 11 In 2021, Chen and co-workers developed the first photocatalyzed oxyalkynylation of the C-C bond of aminocyclopropanes (Scheme 1C1). 12 During preparation of this manuscript, Studer and co-workers reported in January 2022 the first addition of EBX reagents to the C-C bond of arylcyclopropanes (Scheme 1C2). 13 Both methods required a careful optimization of additives and photocatalyst for success.