Investors love dividends. All things being equal, investors will always prefer to be paid more than less. However, what is considered a high-yield in the S&P 500 today is just 3% or more.

So what happens when investors begin looking for dividend yields as high as 8%, 10% or even more than 15%? 24/7 Wall St. would consider this the dangerous dividend arena, where only the most aggressive investors should consider stocks with such high yields.

Click here to see the 9 high-yield dividends for risk takers

Click here to see the 10 safest high-yield dividends

When dividend yields get too high, investors have to do extra analysis. Many companies with such high payouts are structured differently than a normal publicly traded company. These include unconventional real estate investment trusts (REITs), master limited partnerships (MLPs), business development companies (BDCs) and private equity companies.

Investors should also be extra diligent and question whether such companies can maintain their high yields. If income and cash flows are not suitable to cover the dividend payouts in the future, then there may be trouble. That is certainly not always the case, but investors have to do their homework.

When a company raises its dividend, that is an implied nod that the company has visibility or an expectation that it can keep paying those dividends for some time into the future. Things just don’t always go as investors hope. Still, some investors seem to just love high payouts no matter what the risks are.

24/7 Wall St. has evaluated nine high-yielding companies we consider to be only for the most aggressive investors pursuing high income. We selected companies with high dividend yields that either have made irregular payments to investors, have limited earnings coverage for their dividends or have otherwise have faced issues that created uncertainty for investors.

That being said, some of these companies may sustain their dividends for quite some time, if management can appropriately manage cash flows. Some yields featured here are pure dividends, but some are considered dividend equivalent yields because they include a return on capital and are technically distributions.

1. Annaly Capital Management
> Dividend yield: 11.10%
> Annualized dividend: $1.20
> Share price: $10.83
> 52-week range: $9.66 – $12.22
> P/E ratio: 9.26
> Industry: Real Estate

Annaly Capital Management Inc. (NYSE: NLY) is a high-yield mortgage REIT. Because mortgage REITs use leverage to buy mortgage-backed securities, the sector is extremely sensitive to changes in interest rates. The Federal Reserve is widely expected to raise interest rates in 2015, with many Fed policymakers expecting rates to rise even further in the years ahead. The Fed is also expected to begin shrinking the size of its more than $4 trillion balance sheet, with some $1.7 trillion held in mortgage-backed securities. Annaly may still have a very high 11% yield, but its 30 cent per quarter dividend has been in decline since peaking at 75 cents in 2009. This $1.20 annualized dividend compares to an earnings per share (EPS) estimate of $1.17 for fiscal year 2014 and $1.26 for fiscal year 2015. The good news is that the current share price, at $10.83, is below the consensus analyst price target of roughly $11.80.

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2. Transocean
> Dividend yield: 9.50%
> Annualized dividend: $3.00
> Share price: $30.94
> 52-week range: $30.07 – $55.74
> P/E ratio: 6.71
> Industry: Oilfield Services, Offshore Drilling

Transocean Ltd. (NYSE: RIG) has such a high-yield dividend that it seems hard to imagine it not being cut. However, the verdict remains out as to whether the offshore driller can continue to pay a dividend of 75 cents each quarter — or $3.00 each year. Transocean’s 2013 EPS came to $4.11, and while EPS is expected to rise to $4.61 in 2014, it is also expected to fall to just $3.04 per share in 2015. On top of that, analysts expect revenues to drop 5% in 2014 and 4% in 2015. The company recently brought the Transocean Partners LLC MLP public in order to fund new fleet purchases, as well as its dividend. The company also changed its domicile to Switzerland, back before tax inversions became common. Maybe Transocean will keep up its dividend, but it is definitely a risky one.

3. Windstream Holdings
> Dividend yield: 9.10%
> Annualized dividend: $1.00 now; $0.70 ahead
> Share price: $10.61
> 52-week range: $7.18 – $13.30
> P/E ratio: 53.05
> Industry: Telecommunications

Windstream Holdings Inc. (NYSE: WIN) is a communications and cloud services provider for businesses. Short interest in the stock is high, at over 61 million shares and a days-to-cover ratio of 10.8. Windstream may have a found a way to keep its dividend going strong, while simultaneously silencing its dividend critics and short sellers. The company has benefited from plans to spin off its assets into a publicly traded REIT. According to the company’s release in July:

Following the spinoff, the expected annual dividend per share in the aggregate for the two companies will be $0.70 per current Windstream share, with Windstream expected to pay an annual dividend of $0.10, while the REIT will have an annual dividend equivalent to $0.60.

Windstream shares responded favorably to the announcement. The company’s past $1.00 payout, and $0.70 combined payout ahead, compares to EPS in 2013 of $0.35, $0.20 estimated for 2014 and $0.30 per share for 2015.

4. Noble Corp.
> Dividend yield: 7.4%
> Annualized dividend: $1.50
> Share price: $20.60
> 52-week range: $20.06 – $35.54
> P/E ratio: 6.80
> Industry: Oil and Gas

Noble Corp. (NYSE: NE) could find itself caught in a tough spot, after tripling its dividend in less than two years. A share price drop, from about $35 at the end of 2013 to under $21 today, has also contributed to Noble’s high dividend yield of 7.4%. Noble’s current $1.50 annualized payout follows a dividend hike in early August, before the last major slide in stock price took place. Earnings are volatile as well: at $2.89 per share in 2013, with estimates of $3.02 for 2014 and $2.50 for 2015. This $5.25 billion market cap company also runs with a tight balance sheet as far as cash. If offshore drilling doesn’t implode or if things turn around, then its dividend could become safer.

5. Frontier Communications
> Dividend yield: 6.20%
> Annualized dividend: $0.40
> Share price: $6.16
> 52-week range: $4.21 – $7.24
> P/E ratio: 31.75
> Industry: Telecommunications

Frontier Communications Corp. (NASDAQ: FTR) has a 6.2% dividend yield — higher than blue chips AT&T and Verizon. The $0.40 annualized dividend for Frontier is far greater than EPS of $0.24 for 2013, as well as estimates of $0.20 per share in 2014 and $0.22 in 2015. Frontier’s short interest was a whopping 209 million shares in late February, and despite having fallen to 149 million shares by mid-September, it was still quite high. Frontier’s $6.16 share price compares to a consensus analyst price target of $6.06. However, analysts have wide-ranging opinions about Frontier. One analyst sees the company as worth $7.50, while Morgan Stanley recently changed its rating from Equal Weight to Underweight.

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6. Iron Mountain
> Dividend yield: 5.70%
> Annualized dividend: $1.90
> Share price: $32.50
> 52-week range: $23.13 – $34.31
> P/E ratio: 24.60
> Industry: Document Storage

Iron Mountain Inc. (NYSE: IRM) finds itself among the most risky dividends despite recently winning approval from the IRS to convert into a REIT. The storage and information management giant had a mid-September short interest of 13.3 million shares, the highest since the end of 2013. Analysts have a consensus price target of $35.10 for Iron Mountain. The current annualized payout of $1.90 is still above the formal consensus EPS estimates of $1.34 in 2014 and $1.36 in 2015. However, it is often difficult to compare distribution payouts from REITs with dividend payments from typical companies. The long and short of the matter is that Iron Mountain’s payments ahead could be the same, or they could be lower or higher.

7. CVR Refining
> Dividend yield: 17.10%
> Annualized dividend: $3.84
> Share price: $23.00
> 52-week range: $20.16 – $28.55
> P/E ratio: 5.41
> Industry: Oil and Gas

CVR Refining L.P. (NYSE: CVRR) is a downstream energy limited partnership. The partnership refines crude oil at two facilities, one in Coffeyville, Kan., with a capacity of 115,000 barrels per day, and another in Wynnewood, Okla., with a capacity of 70,000 barrels per day. CVR Refining’s Coffeeville refinery was shut down from July 29 through September 2 as a result of a fire. While the company reported a quarterly distribution of $0.96 on July 31, just two days after the fire, this was lower than the $0.98 distribution announced the previous quarter. The key question now is whether that payout can be maintained. Having one plant down for almost five weeks did not help the company, which lowered its forecast for barrel-per-day production. Additionally, payouts have been volatile since CVR Refining’s early 2013 initial public offering.

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8. Prospect Capital
> Dividend yield: 12.8%
> Annualized dividend: $1.33
> Share price: $9.74
> 52-week range: $9.17 – $11.53
> P/E ratio: 8.35
> Industry: Financial Services

Prospect Capital Corp. (NASDAQ: PSEC) is a high-yield BDC. It is involved in all aspects of financing for middle market companies and is one of the larger companies in its industry, with a $3.3 billion market cap. Its dividend yield is close to 13% and payouts occur monthly, rather than quarterly, which is typical for such companies. However, Prospect has not raised its $0.11 monthly distribution — $1.33 annualized — in almost two years. This payout is also above 2013 EPS of $1.19, as well as forecast EPS of $1.17 in each 2014 and 2015. Interestingly enough, Prospect’s $9.74 share price is lower than its stated $10.56 book value per share as of June 30 and even lower than the consensus analyst target of $11.13.

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9. Kohlberg Kravis Roberts & Co.
> Dividend yield: 12.40%
> Annualized dividend: $2.68
> Share price: $21.55
> 52-week range: $19.68 – $26.50
> P/E ratio: 8.42
> Industry: Financial Services

Kohlberg Kravis Roberts & Co. L.P. (NYSE: KKR) is one of the best-known private equity firms in the world. Its market cap is nearly $9 billion, and the firm’s distributions vary wildly from quarter to quarter. A $0.67 payout in July was the highest quarterly payout since February of 2013, so it may be difficult to imagine a yield of 12% being sustainable or even normal. An average of the past two years’ payouts would be closer to $0.43 per quarter. Another issue is that the units in the partnership trade much closer to 52-week lows than highs, a sign that investors may not want to expect such high payouts to become routine. Still, $2.68 in annualized payouts compares to per unit earnings of $2.99 in 2013 and per unit estimates of $2.59 in both 2014 and 2015.

Click here to see the 10 safest high-yield dividends

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