Washington remains the leading arms supplier to Taiwan but has historically been cautious in holding official contacts with it.
Throughout the 1990s the United States sent trade officials to Taiwan with regularity.
Douglas Paal, a former head of the American Institute in Taiwan, Washington's de facto embassy, said the Trump administration was still paying heed to China's red line — that no US official handling national security visit Taiwan.
The difference this time, he said, is the context, with Azar traveling at a time when relations between Washington and Beijing have hit a new low.
"Sending him to Taiwan shows respect for the old framework while putting a finger in China's eye at the same time," Paal said.
"The fact that they didn't choose to send a national security advisor or someone else suggests they are trying to come as close as possible to China's red line but don't want to cross it."
The last cabinet minister to visit Taiwan was in 2014 when the then head of the Environmental Protection Agency led a delegation.
But Washington has billed Azar's visit as the highest level trip made by a senior administration official since the diplomatic switch.
(Writers & Editors: Amber Wang, Shaun Tandon, Agence France-Presse)
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