Cross-Border Tax Planning

Canadian and American flags in the mountains.

Corporations engaged in cross-border operations, including financings, acquisitions and divestitures, face unique and complex tax issues. To ensure dealings are structured to maximize tax efficiencies and minimize tax liabilities, businesses must be aware of and comply with all relevant tax legislation and regulations on both sides of the border.  With today’s climate of increased scrutiny from both tax authorities and the public, the potential reputational and financial impacts of non-compliance cannot be underestimated.

Perhaps most imperative, however, is the need for strategic, sophisticated and integrated advice that takes into account foreign tax laws and how they interact with Canadian tax planning strategies and guidelines. Ultimately, it’s critical that the corporation obtains reliable and consistent guidance that results in the business reducing its tax burden, taking advantage of available tax incentives and refunds, and repatriating its profits at a manageable tax cost. 

Clients involved in cross-border business activities benefit most from tax advisors who can reconcile the differences between Canadian and foreign laws and deliver integrated tax planning guidance with top tax advisers around the world on developing innovative cross-border acquisition, operating and exit structures. Osler’s tax practice group handles a significant amount of cross-border activity in key areas such as emerging companies (financings and acquisitions), cross-border tax planning, Canadian pension funds investing in U.S. assets, transactional insurance matters, mid-market cross-border M&A, and in our private client practice. This experience enables Osler to provide comprehensive guidance; clients can obtain all of their business-critical advice from a single firm – an efficient and cost-effective solution.

In particular, the lawyers in our innovative and creative tax advisory practice

  • provide clients with advice on the tax treatment of cross-border and domestic transactions and multinationals. We advise on structuring and operating transactions, including M&A, financings, restructurings, public company stock acquisitions, joint ventures, project financings, cross-border security issuances, inbound and outbound securities, real estate and private equity partnerships, as well as the tax-efficient repatriation of profits
  • assist clients with inbound and outbound tax planning considerations, including treaty-based planning, international joint ventures, permanent establishment considerations and the development of innovative cross-border structures
  • specialize in the development and implementation of customized tax-efficient cross-border financing arrangements

Representative work

Osler has provided cross-border taxation advice to both Canadian and U.S. corporations from a broad range of sectors, including energy, telecommunications, manufacturing, private equity, big tech, financial institutions and pension funds.

The Canadian corporate clients our lawyers have represented include

  • large, public issuers headquartered in Canada who are doing business in the United States, have significant U.S. assets, are engaged in U.S.-based joint ventures and/or are making significant investments in the United States
  • Canadian clients of all sizes on the acquisition/disposition of U.S. targets, and on U.S. debt and equity financings (i.e., emerging, mid-market, and large public and private companies)
  • Canadian governmental and private pension funds in structuring and negotiating their investments (e.g., hedge funds, private equity funds and other private investment vehicles), including designing co-investments and direct investment structures in the United States and globally
  • private equity fund sponsors on the U.S. tax aspects of fund formation, management and operation

In addition, we have acted on behalf of U.S. clients acquiring or disposing of Canadian targets as well as U.S.-based clients in need of Canadian tax expertise regarding spin-offs, tax-free and taxable reorganizations and acquisitions, and the structuring, operating and unwinding of joint venture arrangements.





  • Kudu Investment Management

    Kudu Investment Management in its minority stake in Third Eye Capital

  • Wealthsimple

    Wealthsimple in its $750 million financing

  • MindBeacon

    IPO of MindBeacon Holdings Inc.

  • Verafin

    Verafin in its US$2.75 billion acquisition by Nasdaq

  • Morgan Stanley

    Morgan Stanley in its acquisition of Solium Capital for $1.1 billion

  • ClearBanc

    ClearBanc in its US$70 million in Seed and Series A financing

  • Veresen Inc.

    Veresen Inc. in its $9.7 billion arrangement agreement with Pembina Pipeline Corporation

  • Whistler Blackcomb Holdings Inc.

    Whistler Blackcomb Holdings Inc. in its $1.4 billion acquisition by Vail Resorts

  • Emera Inc.

    Emera Inc. in its US$10.4 billion acquisition of TECO Energy Inc. and $1.9 billion Bought Deal Offering of Convertible Debentures

  • Mitel Networks Corporation

    Mitel in its proposed $1.96 billion acquisition of Polycom

  • Torstar Corporation

    Torstar Corporation in its $200 million acquisition of an interest in VerticalScope Holdings Inc.

  • Robert Mandel, Investor in Ingersoll Tillage Group

    Robert Mandel and Ingersoll Tillage Group, on ONCAP’s significant investment in ITG

  • Pure Energies Group Inc.

    Pure Energies Group Inc., in relation to its sale to NRG Energy, Inc., a company listed on the New York Stock Exchange with a market capitalization of approximately $10 billion.

  • Affinium Pharmaceuticals

    Affinium Pharmaceuticals in connection with its sale to Debiopharm.

  • Chemtrade Logistics Income Fund

    Chemtrade Logistics Income Fund in its US$860 million proposed acquisition of General Chemical Holding Company. Osler New York and Toronto offices are involved in this transaction.

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