The Boundary Between Legitimate Tax Planning and an Artificial Transaction
The District Court’s judgment in the Q Cyber case (relating to NSO) is one of the most notable recent decisions in the field of international taxation. Its significance does not lie in any sweeping determination that the repayment of a loan necessarily constitutes a dividend. Rather, it lies in the way it sharpens the boundary between permissible tax planning and an artificial transaction, where the structure enables profits to be extracted from Israel to a foreign company without incurring the second layer of tax that would ordinarily apply to a dividend distribution.
At the centre of the dispute was the 2014 acquisition of NSO. The foreign private equity fund Francisco Partners acted through its Luxembourg parent company, OSY. Instead of holding the NSO shares directly through a foreign company, the structure used an Israeli shelf company, Q Cyber, which received shareholder loans from OSY for the purpose of the acquisition. Thereafter, between 2014 and 2018, those loans to the parent company were repaid using funds derived from NSO’s profits, whether by way of intercompany loans or dividends distributed to Q Cyber. The economic result of the structure was the extraction of more than USD 86 million from Israel to a foreign company, with a significant tax saving compared with the alternative of a direct dividend distribution to a non-Israeli resident company.
The key legal distinction in the judgment is that the respondent did not ultimately maintain a “different classification” argument, namely that the loan repayments were, in and of themselves, dividends. Instead, the case focused on the contention that the arrangement constituted an artificial transaction under section 86 of the Income Tax Ordinance. The Court accepted that argument on that basis. In other words, the judgment does not establish that every shareholder loan repaid out of a company’s profits is a disguised dividend distribution. Rather, it holds that where a structure is chosen whose practical effect is to circumvent the tax that would otherwise be imposed on the extraction of profits abroad, the taxpayer must demonstrate that the structure was grounded in a fundamental commercial rationale and not merely in a fiscal advantage.
That is also the judgment’s central point of balance. The Court reiterated the principle that a taxpayer is entitled to arrange its affairs so that its tax liability is lower and is not obliged to choose the route that results in the highest tax charge. Nor did the respondent dispute the legitimacy, in principle, of a leveraged acquisition or the use of debt to acquire a company. However, in this case, once a clear and substantial tax benefit had been shown, the burden shifted to the appellant to prove, by real evidence, that the structure selected served a substantive commercial purpose. That is the heart of the judgment.
The appellant sought to identify several commercial reasons. It argued that Q Cyber was intended to serve as a platform for the acquisition of additional Israeli cyber companies, that it was meant to centralise marketing and distribution activities for the group, and that there were also regulatory considerations relating to defence export control. The Court did not reject, as a matter of principle, the possibility that such reasons could justify an Israeli holding structure. It even noted, in relation to the marketing and distribution activity, that the time required for that activity to take shape was not inherently unreasonable. Nevertheless, it held that these arguments had not been proved to the required standard and, in particular, that it had not been shown that they genuinely underpinned the real-time decision to hold the NSO shares specifically through the Israeli company.
This is where the case failed on the evidence, but not merely in a narrow or technical sense. The Court attached considerable weight to the fact that no representative of Francisco Partners was called to testify who could explain the decision-making process at the relevant time, and in particular that Eran Gorov, who had been involved on behalf of the fund in Israel, was not called. In parallel, the appellant produced very little contemporaneous documentation, such as records of discussions, internal memoranda, opinions, due diligence materials or other documents that might have explained why this structure had been selected. In the absence of witnesses and documents, the argument that there was a fundamental commercial purpose remained general and unsubstantiated.
The evidential difficulty was compounded by factual findings that did not sit comfortably with the commercial narrative presented. Questions arose regarding the timing of the decision to use Q Cyber, including in light of the trust arrangement and the manner in which the transaction was described in the financial statements and in communications with the tax authorities. In addition, the acquisition funds and the repayment funds did not in practice flow through Q Cyber’s bank accounts, but were often transferred directly between NSO and OSY. Although the accounting records reflected the structure, the Court was persuaded that there was a gap between the formal planning and the way matters were actually conducted. Such a gap is not always decisive in itself, but in a case where significant support is in any event required for the alleged commercial rationale, it operates against the taxpayer.
Another important aspect of the judgment is the distinction between business activity that develops at a later stage and the rationale for structuring the transaction at inception. There was no dispute that, from 2016 onwards, Q Cyber had real marketing and distribution activity, with employees, revenue and a tax assessment agreement reflecting a degree of recognition of that activity. However, the Court held that this activity, even if genuine, did not answer the central question in the proceedings: what was the fundamental reason for the 2014 decision to hold the NSO shares through Q Cyber? The judgment contains a clear warning against relying on activity that is developed later in order to justify retrospectively a structure that was chosen earlier.
This also leads to the case’s principal practical lesson. In my view, it would be inaccurate to describe the judgment as saying that “the planning was sound, but the execution was less successful”. That formulation is too lenient towards what the Court regarded as an aggressive structure whose outcome was the circumvention of tax on dividend distributions abroad. Equally, however, it would be wrong to read the judgment as condemning debt pushdown or leveraged acquisitions in Israel as such. The more precise message is different: the clearer and more pronounced the fiscal advantage of the structure, the greater the burden on the taxpayer to show that the structure rests on genuine business logic, is properly documented and is implemented consistently. Where the evidence is thin, where the relevant witnesses are not called, and where the actual conduct does not fully align with the legal structure, the Court will be prepared to treat the arrangement as an artificial transaction.
At the same time, it is equally important to note what the Court did not say. It did not hold that the use of an Israeli acquisition company is inherently objectionable. It did not hold that the repayment of a loan is always a dividend. Nor did it view the appellant’s conduct as fraudulent. This was reflected in its decision to cancel the penalty for failure to withhold tax at source, even though it dismissed the appeal on the merits. That serves as a reminder that even where tax planning does not survive scrutiny under section 86, not every case amounts to false reporting or serious misconduct.
From a practical perspective, the judgment requires particular care in any cross-border transaction involving debt and an intermediate Israeli structure. First, the commercial justification for the holding structure and the financing route should be articulated in real time, rather than being left to later explanations. Secondly, an orderly documentary record should be maintained of the discussions, recommendations, reviews and deliberations that preceded the transaction. Thirdly, care should be taken to ensure that actual implementation, including cash flows and corporate governance, is consistent with the legal and accounting structure. Fourthly, where reliance is placed on regulatory, commercial or strategic considerations, it must be possible to show not only that they are reasonable in the abstract, but that they in fact formed the basis for the specific decision taken.
In that sense, the Q Cyber judgment is not a judgment against tax planning. It is a judgment in favour of tax planning that can be defended. In complex transactions, particularly those that generate significant tax savings, a sophisticated legal structure is not enough. A genuine commercial foundation, full documentation and careful implementation are also required. Anyone seeking to benefit from the flexibility that the law permits must also be prepared, in advance, for the day on which they may be required to explain why this particular route was chosen.



