Guggenheim Strategic Opportunities Fund : GOF Annual Report May 2023

5.31.2023

Guggenheim Funds Annual Report

Guggenheim Strategic Opportunities Fund

GuggenheimInvestments.com

CEF-GOF-AR-0523

GUGGENHEIMINVESTMENTS.COM/GOF

... YOUR WINDOW TO THE LATEST, MOST UP-TO-DATE INFORMATION ABOUT GUGGENHEIM STRATEGIC OPPORTUNITIES FUND

The shareholder report you are reading right now is just the beginning of the story. Online at guggenheiminvestments.com/gof, you will find:

• Daily, weekly and monthly data on share prices, net asset values, distributions and more
• Portfolio overviews and performance analyses
• Announcements, press releases and special notices
• Fund and adviser contact information

Guggenheim Partners Investment Management, LLC and Guggenheim Funds Investment Advisors, LLC are continually updating and expanding shareholder information services on the Fund's website in an ongoing effort to provide you with the most current information about how your Fund's assets are managed and the results of our efforts. It is just one more small way we are working to keep you better informed about your investment in the Fund.

DEAR SHAREHOLDER (Unaudited)

May 31, 2023

We thank you for your investment in the Guggenheim Strategic Opportunities Fund (the "Fund"). This report covers the Fund's performance for the 12-month period ended May 31, 2023 (the "Reporting Period").

To learn more about the Fund's performance and investment strategy, we encourage you to read the Economic and Market Overview and the Management's Discussion of Fund Performance, which begin on page 5. There you will find information on Guggenheim's investment philosophy, views on the economy and market environment, and information about the factors that impacted the Fund's performance during the Reporting Period.

The Fund's investment objective is to maximize total return through a combination of current income and capital appreciation. The Fund pursues a relative value-based investment philosophy. The Fund's sub-adviser seeks to combine a credit-managedfixed-income portfolio with access to a diversified pool of alternative investments and equity strategies.

All Fund returns cited-whether based on net asset value ("NAV") or market price-assume the reinvestment of all distributions. For the Reporting Period, the Fund provided a total return based on market price of 0.80% and a total return based on NAV of 2.09%. At the end of the Reporting Period, the Fund's market price of $15.69 per share represented a premium of 27.15% to its NAV of $12.34 per share.

Past performance is not a guarantee of future results. All NAV returns include the deduction of management fees, operating expenses, and all other Fund expenses. The market price of the Fund's shares fluctuates from time to time, and it may be higher or lower than the Fund's NAV.

During the Reporting Period, the Fund paid a monthly distribution of $0.1821 per share. The most recent distribution represents an annualized distribution rate of 13.93% based on the Fund's closing market price of $15.69 per share at the end of the Reporting Period.

The Fund's distribution rate is not constant and the amount of distributions, when declared by the Fund's Board of Trustees, is subject to change. There is no guarantee of any future distribution or that the current returns and distribution rate will be maintained. Please see the Distributions to Shareholders & Annualized Distribution Rate table on page 15, and Note 2(f) on page 84 for more information on distributions for the period.

We encourage shareholders to consider the opportunity to reinvest their distributions from the Fund through the Dividend Reinvestment Plan ("DRIP"), which is described on page 211 of this report. When shares trade at a discount to NAV, the DRIP takes advantage of the discount by reinvesting the monthly dividend distribution in common shares of the Fund purchased in the market at a price less than NAV. Conversely, when the market price of the Fund's common shares is at a premium above NAV, the DRIP

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND ANNUAL REPORT l 3

DEAR SHAREHOLDER (Unaudited) continued

May 31, 2023

reinvests participants' dividends in newly issued common shares at the greater of NAV per share or 95% of the market price per share. The DRIP provides a cost-effective means to accumulate additional shares and enjoy the benefits of compounding returns over time. The DRIP effectively provides an income averaging technique for shareholders to accumulate a larger number of Fund shares when the market price is depressed than when the price is higher.

We appreciate your investment and look forward to serving your investment needs in the future. For the most up-to-date information on your investment, please visit the Fund's website at guggenheiminvestments.com/gof.

Sincerely,

Guggenheim Funds Investment Advisors, LLC

Guggenheim Strategic Opportunities Fund

June 30, 2023

4 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND ANNUAL REPORT

ECONOMIC AND MARKET OVERVIEW (Unaudited)

May 31, 2023

Caution over the lagged effects of monetary tightening and banking sector stability led to the U.S. Federal Reserve (the "Fed") foregoing a hike at the June 2023 meeting, but this dovish decision was somewhat offset by a projection of two more hikes during 2023. We see a hike in July as a very high probability, and we believe the odds the Fed will need to deliver a second hike are rising as financial conditions ease and evidence mounts of some resurgence in the housing market. The Fed is wary of letting financial conditions ease too far and too fast, which could undo the economic impact of the aggressive rate hikes to-date.

Market hopes for a soft landing seem to have risen as some progress is being made on inflation and the labor market has stayed resilient. We continue to see an elevated probability of a recession starting this year as the Fed continues to explicitly target a weaker labor market, and believe several leading indicators point to rising unemployment later this year as backlogs in hiring are alleviated and employers may resort to layoffs after aggressively shedding hours this year. Consumption also faces headwinds from dwindling excess savings buffers and services consumption that has now returned to trend, indicating the boost from pent up demand may be behind us.

With pressure still on the banking sector, we expect a further tightening in bank lending standards resulting in a further slowdown in credit growth. Business investment may slow further as a result.

Because private sector balance sheets appear to us to be generally healthy in the aggregate and the economy lacks major imbalances, we do not expect a particularly deep recession. Additionally, two of the most cyclical sectors, housing, and autos, are out of sync with the broader cycle and could be smaller drags than is typical during a recession.

Inflation may trend lower over the next year, helped by housing-related inflation cooling. Services inflation outside of shelter is the main concern for the Fed, but a softening labor market and slowing wage growth could gradually bring this category down as well. We expect core inflation to fall close to 2% in 2024. As evidence mounts that inflation is heading back toward target and the rise in unemployment gets more substantial, we could see large rate cuts in 2024 and early 2025.

The opinions and forecasts expressed may not actually come to pass. This information is subject to change at any time, based on market and other conditions, and should not be construed as a recommendation of any specific security or strategy.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND ANNUAL REPORT l 5