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TALLINN, ESTONIA - Let's face it: NATO summits aren't usually the most scintillating gatherings.

"President Obama has supposedly said that he finds these things dull," said Jeremy Shapiro, a fellow at the Brookings Institution. "[Former Secretary of Defense] Robert Gates reportedly wouldn’t go to NATO meetings unless his staff supplied him with a sufficient number of crossword puzzles."

But the summit to take place this week in Wales should buck the trend.

There's a whole lot riding on this week's summit in Wales and the trip President Obama will take here to Estonia the day before the gathering begins. There are, to put it mildly, quite a few things going on in the world, from Ukraine to Iraq to Afghanistan. The NATO summit will address them all and more.

Here are a couple of key items on Obama's to-do list this time around -- reasons this week's jaunt is worth watching:

1. Reassuring those in Russia's shadow

President Obama's first stop is in Tallinn, where he arrives Wednesday morning. The president's job here is a substantial one: to reaffirm to NATO members Estonia, Latvia and Lithuania the organization's commitment to Article 5, which states that if a NATO member is attacked other countries in the alliance will come to its defense.

This principle has taken on a whole new specter since Russia annexed Crimea earlier this year. The Baltic states -- all former Soviet republics that have Russian-speaking minorities -- are anxious and fear that Russia's incursion into Crimea could lead to it doing the same in other former Soviet republics in the future. German Chancellor Angela Merkel made a trip to Latvia last month to also affirm the commitment to Article 5.

"You have in Estonia a large Russian population, and therefore part of the message that the President will be sending is, we stand with you; Article 5 constitutes an ironclad guarantee of your security; Russia, don’t even think about messing around in Estonia or in any of the Baltic areas in the same way that you have been messing around in Ukraine," Charles Kupchan, senior director for European Affairs at the National Security Council, told reporters.

1a. Dealing with Russia's shadow again, some more

Ukraine is likely to be the top item on the NATO agenda. The nation is not a NATO member, though it has asked to be one -- but Ukrainian President Petro Poroshenko will still be at the Wales gathering.

The meeting comes as developments in the region are changing and escalating quickly. NATO members, including the U.S., have said Russian President Vladimir Putin has significantly upped the ante in the crisis as Ukrainian territory has been lost and reports of Russian tanks and equipment inside the country increase.

NATO will announce a Readiness Action Plan to respond to Russia's "aggressive behavior," NATO Secretary General Anders Fogh Rasmussen said Monday, and plans to open bases in Eastern Europe.

"Russia is intervening overtly in Ukraine,” Fogh Rasmussen said.

While NATO does not have the power to enact additional sanctions against Russia, a senior Western diplomat said it is "quite likely" that there will be more from the European Union.

There are also reports that NATO will ratify a measure that says a cyberattack on one of the countries will warrant a collective defense response -- a clear message aimed at Russia.

2. Taking aim at the Islamic State

The threat posed by the Islamic State, the Islamic Militant group that beheaded American journalist James Foley and claims to have beheaded journalist Steven Sotloff, is going to be a major topic of discussion at the summit. British Prime Minister David Cameron raised his nation's terror threat level last week, and Monday called for new laws that would, among other things, allow for the passport of a person believed to be traveling for the Islamic State to be seized and give authorities more power to track suspected militants.

One of the objectives of the summit will be to "advance NATO’s role as a global security hub," Kupchan said.

"And this hopefully will include support at NATO for engaging in the Iraq and Syrian theater," he said. President Obama has ordered air strikes against the Islamic State in Iraq, but not yet decided whether or not the United States will intervene militarily in Syria.

Kupchan said NATO will discuss how it can "further its role as a hub of global security," including how to use NATO assets to offer assistance to other countries and regions as it has in Europe.

"I think the President is forward leaning on getting NATO more involved in the Middle East and, in particular, dealing with the threat from ISIL, dealing with the humanitarian urgencies in the region. And so one can expect NATO to make advances on that front," he told reporters.

3. Dealing with unanswered questions in Afghanistan

NATO is drawing down its forces in Afghanistan. But the country is now mired in political uncertainty, with the results of a presidential runoff election in dispute, and the second-place candidate boycotting a recount. The country's new president was supposed to attend the summit -- but with no one in place, there are reports that Afghan Defense Minister Bismillah Mohammadi will show up instead. President Hamid Karzai, who is leaving office, did not sign a bilateral security agreement on U.S. troops in the country.

"After 12 years, NATO can be proud of its legacy in Afghanistan," U.S. Ambassador to NATO Douglas E. Lute wrote. NATO's commitment, he said, doesn't end with the conclusion of the International Security Force's mission at the end of the year. "Much remains to be done but Afghanistan’s future is in the hands of Afghans, while NATO stands ready to support." 

Officials had hoped to finalize the level of support and details of the end of the mission. The political situation puts that up in the air. A senior Western diplomat said officials are focusing on the political process there, and no one wants to reconsider the decisions that have already been made. One thing is clear, though, this person said: NATO is not going to totally walk away from Afghanistan.

"So it is vital to see a conclusion to the electoral process in Afghanistan – a conclusion which is accepted by both candidates, and the Afghan people," said Rasmussen. "So, there is still a lot of work to do."

4. Prying open European wallets

The perennial fight within NATO is all about spending. And it usually plays out the same way: the United States gripes about how other NATO members don't contribute enough money to the organization's collective defense.

President Obama started ringing the alarm again this year, saying he is concerned that not all members are "chipping in" toward the cost of a collective defense and deterrence toward Russia. Back in 2011, then Defense Secretary Robert Gates made a stinging rebuke of NATO allies, saying in Berlin that the United States is tired of engaging in combat with and taking risks for countries that “don’t want to share the risks and the costs.”

The situation in Ukraine has again brought the question of resources to the forefront. NATO wants its members to give 2 percent of their GDP to NATO for defense. Few are doing so. Will things change? Perhaps.

The contribution "has to be meaningful. It has to be purchasing NATO interoperable equipment that can be used both for collective defense, but also for crisis management," Conley said.

But as always, the question comes down to political will: In Western Europe, there's little appetite for increasing defense spending as the continent's economic growth sputters.

"There is no domestic consistency in Western Europe for increasing defense spending relative to healthcare or education or any of those other things," said Thomas Wright, a fellow at the Brookings Institution. The specter of Russian intervention makes Eastern European countries more likely to give money -- but: likely enough so the United States won't still still be chiding members to pay up a year from now? That's an open question.