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NEW YORK (Fortune) -- CIT Group is the first big bailout loss for taxpayers, but it won't be the last.

CIT (CIT, Fortune 500) filed for Chapter 11 bankruptcy protection Sunday. The New York-based small business lender said all its common and preferred shares will be canceled, which will wipe out the $2.3 billion Troubled Asset Relief Program investment the Treasury Department made last December.

Though the government is also highly unlikely to recoup all the money it plowed into AIG, Citigroup, Fannie Mae and General Motors, CIT is the first bailout to go to zero -- in just 11 months, no less.

"Preferred stock is a very risky security," said Linus Wilson, a finance professor at the University of Louisiana at Lafayette. "CIT Group is the first large lesson for taxpayers of its risks."

Unfortunately, it's not likely to be the only lesson.

Typically in bankruptcies, bondholders and creditors are the first in line to get paid back. Owners of a company's stock, even investors in preferred shares that pay special dividends, are usually left holding the bag.

CIT, with $71 billion in assets, missed its quarterly dividend payment due in August. According to a report issued last month by SNL Financial, there were 32 other TARP recipients that did so as well. CIT was by far the largest, being the only firm on the list with more than $1 billion in Treasury loans.

But eight banks that are behind on their dividend payments have at least $100 million in Treasury loans, including two that are publicly trying to raise capital -- a tough task at a time when banks are falling by the wayside at a rapid clip.

To take one recent example, the nine banks controlled by FBOP, Oak Park, Ill., failed Friday, bringing the 2009 failed-bank count to 115. The banks, with assets of $18 billion, failed two months after FBOP -- which didn't get TARP funds -- signed a written agreement with the Federal Reserve pledging to raise capital.

The two big banks on the TARP deadbeat list that have pledged to raise capital are Sterling Financial (STSA) of Spokane, Wash., and UCBH Holdings (UCBH) of San Francisco. Both have more than $12 billion in assets.

Sterling got $303 million from Treasury on Dec. 5. But it missed its Aug. 17 TARP dividend payment after posting a $59 million first-half loss. Then, last month, it consented to a cease-and-desist order from the Federal Deposit Insurance Corp. directing it to raise $300 million in capital.

The company said in a statement Monday that it was evaluating options for acquiring additional capital and that it has hired investment bank Sandler O'Neill and Partners as a financial adviser.

UCBH, the parent of United Commercial Bank, named a new CEO in September after the company's previous chief stepped down amid questions about the bank's accounting. UCBH received $299 million from Treasury last November but said this year it will try to raise money as it investigates the bookkeeping missteps that are expected to lead to an earnings restatement.

Shares of both companies recently fetched less than a dollar each. UCBH has until mid-November to resume filing timely financial statements or face delisting from Nasdaq. A spokesman for UCBH said the bank is "aggressively moving forward" on its capital plan and has hired a financial adviser that will help it consider all its options.

Other big banks that have missed TARP dividend payments include:

• First Bancorp (FBP), San Juan, Puerto Rico, a $20 billion institution that took $400 million in TARP funds in January. It recently shook up its board and named a new CEO, after an investigation by the board's audit committee. A spokesman said the bank stopped paying dividends this summer under federal guidelines that say a bank can pay out dividends only if it is making enough profit to do so.
• First Banks, Clayton, Mo., a $10 billion privately owned bank that received $295 million from Treasury in December. The bank said it stopped paying dividends "in order to maintain liquidity and capital until such time as economic conditions warrant resuming payments."
• Pacific Capital Bancorp (PCBC), a Santa Barbara, Calif., institution that posted a $363 million loss for the second quarter and recently won shareholder backing for a possible reverse stock split. It took $181 million from Treasury last November. A spokeswoman said the bank is preparing for its third-quarter earnings report and declined to comment.
• Closely held Dickinson Financial, Kansas City, Mo., got $146 million in TARP loans in January. Its Southern Commerce Bank unit in Florida was recently cited on the Bankaholic web site for offering the highest rates on a 12-month certificate of deposit -- a strategy strapped banks sometimes use to boost deposit funding.
• Central Pacific Financial (CPF), a Honolulu-based bank that lost $183 million in the third quarter as its commercial real estate book soured. The bank took $135 million from Treasury in January. It shares recently traded at $1.10 apiece.
• Anchor Bancorp (ABCW), a Madison, Wis.-based institution that last month restated its results to show a loss of $63 million for the quarter ended June 30. The firm, which received $110 million in TARP funds in January, cited the deteriorating performance of its loans. The company said in a statement that it also was deferring dividend payments and that "upon the execution of a successful capital event, AnchorBank expects to be able to pay any and all deferred dividends."
  

Deferred dividends aren't the only possible warning sign, of course. South Financial Group (TSFG), Greenville, S.C., said last month it expects to lose $341 million for the third quarter.

The bank, which took $347 million in TARP funds in December, made its third-quarter TARP dividend payment and stressed it remains well capitalized. But its shares haven't risen above $3 apiece since May and recently traded for 75 cents. South Financial didn't immediately respond to a request for comment.

But with the next round of TARP dividends due later this month, it's worth considering that the 32 banks other than CIT that failed to pay their August TARP dividends have together taken $2.3 billion in TARP money. They won't all fail, of course -- but as taxpayers are all too aware, every dollar counts.