Clinton drew the sharpest distinctions yet from her former boss in a rebuke of his cautious approach to global crises.
"Great nations need organising principles, and 'don't do stupid stuff' is not an organising principle," Clinton said in a weekend magazine interview, referring to a version of the phrase Obama and his advisers have used privately to describe his approach to foreign policy.
Clinton wrapped her critiques in expressions of respect for the president and sympathy for the tough global decisions he grapples with from the Oval Office.
Yesterday, a vacation day for Obama, he dealt with issues involving Iraq, Ukraine, Gaza, Syria, as well as terrorism and Ebola in Africa.
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"He's thoughtful, he's incredibly smart, and able to analyse a lot of different factors that are all moving at the same time," she said.
"I think he is cautious because he knows what he inherited, both the two wars and the economic front, and he has expended a lot of capital and energy trying to pull us out of the hole we're in."
The White House said before the interview was published that Obama would not attend and has no plans to see Clinton while they are both on the island.
In a wide-ranging interview with The Atlantic published on its website, Clinton offered an uncompromising defence of Israel's battle against Hamas in Gaza and argued against Obama's decision not to build up a rebel fighting force to confront Syrian President Bashar Assad.
The White House declined to respond to Clinton's comments, but said her team gave them a heads up before the interview was published.