Each case has the distinct earmarks of "selling away," an often problematic practice involving the sale of products not vetted by broker-dealer compliance departments. Mr. Galvin also charged the three firms, Ameriprise Financial Services Inc. of Minneapolis, Gateway Financial Agency Corp. of Oxford, Ark., and New England Securities Corp. of Boston, with failing to supervise the alleged rogue reps properly.

In this day of extraordinary sensitivity, "firms have to be creative and thoughtful," said Lisa Roth, president of ComplianceMAX Financial Corp. in San Diego, a compliance consultant to broker-dealers. "You've got to have thoughtful controls that suit your manner of business."

Ms. Roth said her firm is recommending that broker-dealers ask for a rep's tax records and information about checking accounts. It also recommends using the web search engine Google to uncover details about a broker's past.

Russian roulette

One complaint against Shane A. Selewach, formerly in the Boston office of Ameriprise, alleged that he stole more than $200,000, mostly from older clients, and used that money for personal expenses.

Those expenses included several charges for a dating service touting itself as "the fastest way to meet thousands of Russian ladies." It also included several charges at a florist in Moscow as well as thousands of dollars in restaurant and hotel tabs in Kiev, Ukraine and Moscow, as well as other locations in Russia and Ukraine.

Mr. Selewach, who duped clients by setting up private commodities and real estate funds, also used the money for car and mortgage payments, according to the complaint.

"Ameriprise missed many opportunities to detect and halt Selewach's illegal acts by missing many red flags, failing to comply with rules of the NASD related to review of private securities transactions, and failing to have any meaningful contact with [the broker's] clients even after the firm learned of his scam," according to the complaint. "Indeed, almost all of Selewach's illegal activities occurred after Ameriprise placed him on heightened supervision."

Steven Connolly, a spokesman for Ameriprise, said the firm investigated the original client complaint and paid restitution to the client of $75,000, including interest. Complaints involving other clients occurred after Ameriprise fired Mr. Selewach in April, Mr. Connolly said.

Mr. Connolly said Ameriprise is "disappointed" that Massachusetts included the firm in its complaint, but it is cooperating.

According to a separate complaint by Mr. Galvin, Patricia Ann Palmer, a broker formerly affiliated with Gateway Financial Agency, sold to investors phony certificates of deposit totaling more than $663,000.

Her fraud was part of a larger Ponzi scheme originating in Allentown, Pa., that was orchestrated through the IDPM Group Inc., according to the complaint. In March, the Securities and Exchange Commission charged IDPM with fraud concerning the sale of fake CDs.

Ms. Palmer briefly was affiliated this year with ING Financial Partners of Des Moines, Iowa, which wasn't charged with a failure to supervise.

"Gateway was not aware of these deceptive practices but also did nothing to check to see if anything inappropriate was being done by [Ms.] Palmer," the complaint said.

A call to Gateway Financial wasn't returned

And a third complaint charges that a rep affiliated with New England Securities, Paul Surface, violated state securities laws when he "solicited his clients to make investments in an illiquid, high-risk, unregistered investment and did not report such investments to" the firm.

He "was able to avoid improper outside business activities because of [New England Securities'] lack of diligent supervision and administrative oversight of Surface's business activities," according to the complaint.

In total, Mr. Surface raised more than $600,000 from at least 13 clients at New England Securities in an outside business from which those investors haven't received any type of payment, according to the complaint.

Holly Sheffer, a spokeswoman for MetLife Inc. of New York, the parent of New England Securities, declined to comment on the Massachusetts allegations.