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There is the brief rush of energy before he goes in for a sale. He prepares himself a bit like an actor.

"I try to think of what it would be like to actually want the cigarettes," said Michael, who does not smoke.

Now 18, Michael is in his fourth year of busting clerks who sell tobacco to teens.

Charged with enforcing age restrictions on tobacco sales, state Department of Health and Human Services investigators send kids such as Michael - called "confidential informants" or "youth inspectors" - into gas stations and grocery stores around Alaska.

The state fines and suspends the tobacco endorsements of those who are caught. Last year, from 407 random inspections, the state issued 40 citations and assessed 49 fines for underage tobacco sales, according to a report. Nine endorsements were suspended. None were revoked.

In Juneau this year, the Mendenhall Valley Tesoro, Fred Meyer and a Breeze In have been temporarily forbidden to sell tobacco products. It was Tesoro's second offense.

"Juneau usually does pretty well. Some communities are worse than others," chief investigator Joe Darnell said.

States report to the federal government the rate at which their underage agents get sales. If more than 20 percent, a state runs the risk of losing federal grants for substance abuse prevention.

Alaska's rate was 9.2 percent in 2007. That's below the national average of 10.5 percent, which has decreased each year for the last decade.

Undercover teenagers trying to buy alcohol for the Alcohol and Beverage Commission can lie. And they have other tricks: the well-known "shoulder tap," for example, asking someone else to buy them beer.

But for these tobacco stings, investigators pull no sneaky tricks.

Underage agents are chosen because they look no older than their age. They dress in age-appropriate clothing. The boys are clean-shaven. Not even a baseball cap can shade the face. No seductive clothing. They empty their pockets except for money and a state-issued ID, in case a cell phone might look like a pack of cigarettes in a pocket.

The same goes for the kids' behavior. No flirting or manipulation. No lies. Just a straight-up, "I'd like a pack of Marlboro Lights/tin of mint Skoal/cigar."

In the store, Michael picks up a candy bar or a drink, maybe a lighter. Cigarettes are the easiest to ask for if he's a bit nervous. With chewing tobacco, clerks ask a lot of questions.

Darnell said he doesn't send girls to buy chewing tobacco because it seems unlikely they'd do so in real life.

If a clerk asks the agent for an ID, Michael will produce his driver's license. Alaska youth licenses are laid out on the vertical, unlike those of adults, so it's easy enough to tell. If the clerk asks whether he's old enough, Michael will say, "No."

Most clerks check, according to Michael and state statistics.

Sometimes they even lecture him as they deny him.

"I've had quite a few people tell me, 'You shouldn't smoke at your age,'" Michael said.

Awkward.

"They're still holding your ID, so you can't walk away," he said.

Every now and then a clerk takes an ID, enters an earlier birth date into the register query and sells him the tobacco anyway.

Through Michael's head runs a thought perhaps the same as that of a kid actually looking for cigarettes: "Wow, they're actually going to go through with it."

No matter what happens at the counter, Michael plays it cool, leaves with or without the goods, gets back into the investigator's minivan and stays there.

The clerk who carded him will never know he was buzzed. The one who sold the smokes will get an immediate ticket.

The penalty is 20 days suspension of the tobacco sales license for a first offense and a $300 fine. Second and third offenses in a two-year period carry longer suspensions. A change in Alaska law last year means retailers can reduce their suspension time if they do certain things to avoid sales - including checking the IDs of every would-be buyer, even the white-haired.

Danell said investigators don't want to make trouble for the kids, so they take their underage agents to other towns to work. Michael has tried to buy cigarettes in places from Ketchikan to Fairbanks, but never in his hometown, Juneau. Nor would he be asked to sell to anyone he knew.

The state investigators invested time training Michael. Yet they will phase him out once he gets to age 18.5, because they don't want to make clerks mince months.

Like many of his fellow teenage undercover agents, he'll probably move on to pretending to buy alcohol.

• Contact reporter Kate Golden at 523-2276 or kate.golden@juneauempire.com.