Probably won’t be much of a test he already knows Obama just draws lines….

President Obama won’t be able to escape the long shadow of Vladimir Putin when he heads to the United Nations General Assembly this week.

Russia is in the middle of two of the biggest crises on the planet — in Syria and Ukraine — and those vexing challenges will be front and center when Obama meets with Putin Monday on the sidelines of the annual diplomatic gathering in New York.

“When we look at conflict, the president will certainly be focused on the situation in Syria and Iraq, and he’ll be focused on the situation in Ukraine,” White House deputy national security advisor Ben Rhodes told reporters this week.

“Our focus is going to be on the fact that there has to be a cost for a nation like Russia that is violating the sovereignty and territorial integrity of Ukraine.”

“At the same time, in Syria, even as we have an aggressive military effort underway against ISIL, the only lasting resolution to that challenge is for there to be a political settlement, as well,” he added, using an alternate acronym for the Islamic State in Iraq and Syria (ISIS).

The U.S.-Russia dynamic won’t be the only issue when world leaders sit down together in the coming days.

The release of 17 new goals for international development have the prospect of reinvigorating the globe’s efforts to combat extreme poverty, illness and inequality for the next 15 years.

But top military officials have called Russia the U.S.’s most dangerous foe, and the pressure will be on for Obama to successfully navigate the power struggle when the two sit down for talks.

Putin will make his first address at the U.N. meeting in a decade on Monday, and will also head into a bilateral meeting with Obama.

That meeting will be the first time the two leaders have met in person since a brief reunion marking the D-Day anniversary in France last June.

The two nations have been locked in an increasingly bitter standoff in recent years, after Russia entered something of a diplomatic exile following its military intervention in Ukraine.

In 2013, the White House canceled a summit planned for Moscow, in a rare snub against the Kremlin, and it has more recently kicked Russia out of the Group of 8 nations.

Now, Russia is in an awkward position.