The annual Southeast Asia summits, often lacking in other substance, became forums for western democracies and human rights groups to bash Myanmar's poor democratic performance, and by extension, Asean's.
The bloc's agreement to allow Myanmar to chair Asean this year, hosting its first summit on May 10 and 11, marks a watershed of sorts.
Although the chairmanship is supposedly rotated on an annual basis alphabetically, Myanmar used to be consistently passed over due to widespread opposition.
"The biggest thing Myanmar may get from Asean summit is political dignity," said Ko Ko Hlaing, political advisor to Myanmar President Thein Sein.
Myanmar has certainly come a long way in the three years since Thein Sein's took office in March 2011.
His political reforms, which included paving the way for democracy champion Aung San Suu Kyi to join Parliament, led to the dropping of sanctions by western democracies in 2012 and Myanmar's reacceptance in the international arena.
It has been a long, hard haul for Asean to get this far.
"The fact that Myanmar has become chairman of Asean says volumes about the aspiration of Asean to integrate the region," said Surin Pitsuwan, former Asean secretray-general who did his fair share of Myanmar damage control while in the post.
"Now it's up to Asean to synchronise itself with the region, both in terms of hardware and software," he said.
Surin's "software" was a reference to lingering concerns about Myanmar's human rights record, specifically the recent hike in anti-Muslim violence, directed mostly against the Rohingya Muslim minority group in Rakhine State.
"Myanmar's chairmanship of Asean this year is being side-tracked and increasingly eclipsed by other preoccupations," said Thitinan Pongsudhirak, director of the Institute of Security and International Studies (ISIS) at Thailand's Chulalongkorn University. "When we get news on Myanmar nowadays it's all about the Rohingya and Rakhine," he said.
Sectarian fighting broke out between the Rakhine's Buddhists and Rohingya Muslims in 2012, leaving up to 200 dead and 140,000 displaced, most of them Muslims.
The positive news that Myanmar conducted its first census in three decades last month was overshadowed by authorities' refusal to allow Rohingya - deemed stateless under the 1982 Citizens Act - to register as a distinct ethnic group.
Myanmar authorities refer to the Rohingya as Bengali, reflecting the official position that considers them illegal migrants from neighbouring Bangladesh.
It is unlikely that the Roghingya issue will be raised, at least officially, at the Asean Summit in Naypyitaw.
"The Bengali issue is not a regional issue, just a local issue," Ko Ko Hlaing said. "No one will try to raise this issue at the summit because, in keeping with Asean practice, it will not be discussed if a member opposes the issue."
Since the group's founding in 1967, Asean members have stuck to a principle of "non-interference" in each another's domestic matters, a stance that has repeatedly called into question the grouping's effectiveness as a regional peace-keeper and standards setter.
Asean's common goal in accepting Myanmar into its fold in 1997 was partly about keeping the South-East Asian nation out of Beijing's orbit, observers said, and there is little doubt that Myanmar's recent reforms were partly an effort to reduce its dependence on China, its giant neighbour to the north.
China is currently Myanmar's leading trade and investment partner. As of March, 2014, China's total investments in Myanmar amounted to 14.2 billion dollars, or 30.8% of the total.
Thailand is the second foreign direct investor with 10.1 billion.
The regionally sensitive issue of territorial disputes in the South China Sea will also be raised but no one is expecting a breakthrough.
"China is our neighbour and also a world super power," Ko Ko Hlaing said. "Myanmar was heavily dependent on China in almost all sectors while the western countries imposed sanctioned on us. Without China, Myanmar could not even have started its reform process."
With the Rohingya issue not on the agenda, and Myanmar's pragmatic stance on China, observers anticipate another lacklustre Asean summit.
"I think Myanmar would be fortunate to get out of the chairmanship with a minimalist performance," Thitinan said.