It has been almost seven years since Vietnam first experienced its official WTO membership on 2007. At the time of accession, it was envisioned that Vietnam economy would develop rapidly, and the event was hailed as “a turning point” and even “a sacred moment.” Many people in Vietnam said that the country would be “taking off” and becoming “a new Asian tiger”. Then, most enterprises and the Vietnamese feel disappointed with the fact that economic growth has been much lower than expected since Vietnam joined the WTO. There are reasons for such disappointment. First, at that time Vietnamese enterprises did not know or well- prepare for the challenges that lied ahead. Second they were so optimistic about the benefits being received. The history seems to be repeated now when Vietnam are negotiating another important FTA-the Trans-Pacific Strategic Economic Partnership Agreement (hereinafter the TPP) – that is considered as an integration as both breadth and depth level of because it is the largest, most dynamic trade collaboration of 21 century. On the Vietnamese media, major benefits of TPP are analyzed and propagated to create public support in order to conclude the TPP as soon as possible. Even a popular economic research approves that Vietnam is the biggest beneficiary among the TPP countries. Unfortunately, like the WTO, the TPP is not a “delicious cake”, and of course, there is no free lunch for Vietnam. To that respect, the paper aims at researching on the major potential challenges of Vietnam when participation in the TPP so that the community, especially the Vietnamese enterprises, are fully aware of both speculative interest and cost in order to have solutions to minimize the challenges and maximize the opportunities. The paper aims at answering two crucial questions: What is the ambition level of the negotiations? Whether Vietnam is ready for such level of ambition on offers in the TPP and what are the main challenges Vietnam may have to face?To answer the questions, this research paper will be divided into two chapters as follows:Chapter I: “Vietnam’s participation in the TPP negotiations and speculative opportunities”. Serving the introductory purposes, this chapter provides readers with the fundamental knowledge on the TPP negotiations and its ambition level in general, and then Vietnam’s participation and the benefits it may receive in an ideal condition in particular. Chapter II: “Challenges Vietnam may face in the TPP”. This is the main part of the paper which introduces and analyzes the potential negative impacts and difficulties of the proposed regulation in the on-going negotiations for the most important sectors and issues in Vietnam. The chapter is presented with the proposed rules for a sector, then I will analyze the challenge caused by such regulation and finally the solution (if any) for such challenge. First the challenges for textile and apparel sector are analyzed, then for agriculture sector, intellectual propriety rights (IPRs), State-Owned Enterprise reform, legal reform, and labor chapter, respectively.