This article addresses certain cases of intra-group transactions (mainly accessory and ancillary to another "main" transaction) which are capable of resulting in the shifting of (sometimes substantial) profits among group companies (and the relevant tax jurisdictions) even without (or regardless of) a violation of transfer pricing rules and of the arm's length principle. The set of tax rules and regimes potentially applicable to these transactions under Italian law are described and analysed. As international financing arrangements often contain these penalty and earnest clauses, the article provides interesting information and analysis for tax practitioners in the financial arena.