High Income Securities Fund (PCF)

Semi-Annual Report

For the six months ended

February 29, 2024

Table of Contents

Letter to Stockholders

1

Portfolio Composition

4

Portfolio of Investments

5

Statement of Assets and Liabilities

11

Statement of Operations

12

Statements of Changes

13

Financial Highlights

14

Notes to Financial Statements

16

Privacy Policy

44

High Income Securities Fund

April ___, 2024

Dear Fellow Stockholders:

The Fund currently pays monthly distributions at an annualized rate of at least 10% (or 0.8333% per month) of its per share net asset value (NAV) as of the last business day of the previous calendar year. Each of the first two monthly distributions in calendar year 2024 have been $0.0622 per share. Please note that in some calendar years, adhering to the Fund's managed distribution policy may require some capital to be returned to shareholders. The Fund will not know what percentage, if any, of its distributions will be characterized as a return of capital until after the end of the calendar year in which they are made.

During the first half of fiscal year 2024 ending February 29, 2024, the Fund's NAV per share rose a penny from $7.43 to $7.44. After accounting for distributions of $0.3660 cents per share, the return based upon the Fund's NAV was 5.25%. As of February 29, 2024, the Fund's shares were trading at $6.77, a discount of 9.01% to their then-current NAV per share.

As discussed previously, we believe the Fund's investment parameters are unduly restrictive and should be expanded. For example, we would like the flexibility to increase the Fund's exposure to special purpose acquisition companies ("SPACs") (a/k/a blank check companies), which can provide a higher return than a money market fund with minimal risk of incurring a realized loss of principal, provided that the common stock is sold or redeemed before a transaction with an operating company is completed. (Shares of SPACs held after a completed transaction can be very volatile.) Another restriction we would like to relax (and which makes little sense to us) is the limitation on purchasing investment grade bonds. Lastly, we think the Fund should have the ability to prudently use leverage to enhance its returns. To this end, and subject to shareholder approval, a special committee of the Board comprised only of the independent Trustees has recommended that the full Board approve (1) the Fund entering into an investment advisory agreement with Bulldog Investors, LLP, and (2) changes to the Fund's investment strategies and fundamental policies in order to expand the types of investments the Fund can make. Bulldog Investors has more than 25 years of experience in employing activist measures to enhance the value of its clients' investments and is an affiliate of the members of a committee of the Board of Trustees that has been responsible for investing the Fund's assets since 2019.

Unfortunately, the Fund's shareholder base has become increasingly inactive with respect to participation in shareholder meetings. Indeed, less than 22% of the outstanding shares were represented at the annual meeting of shareholders in 2023, well short of a quorum. (Notably, with respect to one proposal to be considered at the meeting, holders of only 5% of the Fund's outstanding shares voted to convert the Fund to an open-end investment company.) With the intent to increase the proportion of shareholders that will actively participate in

1

High Income Securities Fund

shareholder meetings, the Board (1) has authorized the Fund to conduct a rights offering, and (2) intends to authorize a self-tender offer by the Fund to commence shortly after a special meeting to be held to consider the above changes. On April 16, 2024, a press release detailing these measures was issued and is available on the Fund's website.

A primary focus of the Fund's investment strategy has been to acquire discounted shares of closed-end investment companies ("CEFs") and business development companies ("BDCs") that make regular distributions, as well as the senior securities, e.g., notes or preferred shares, of CEFs and BDCs (which we think have a negligible risk of defaulting) and of certain operating companies when they are attractively priced. In addition, units or common shares issued by SPACs may comprise up to 20% of the Fund's portfolio.

In 2019, after the Fund liquidated its entire portfolio prior to conducting a large tender offer, it adopted the ICE BofA Merrill Lynch 6 Month U.S. Treasury Bill Index (which was up 2.78% in the first half of fiscal year 2024) as a "place marker" benchmark. In light of the contemplated expansion of the Fund's investment parameters, the Board will determine whether another available benchmark is more suitable going forward.

The Fund's investments in BDCs have continued to perform well. Since many of their loans have floating interest rates, most BDCs have been raising their dividends as interest rates have increased. Moreover, they have not reported a significant increase in non-accrual loans. The Fund's shares of BDCs generally trade at a significant discount to their NAV and most of them have accretive share repurchase plans in place.

The "off balance sheet" item that we mentioned in our last letter representing a settlement payment of about $170,000 (based upon a legal claim related to one of the Fund's former SPAC holdings, FAST Acquisition Corp.), is now expected to be received by the end of June.

Lastly, we remind you that from time to time the Fund seeks instructions from its stockholders for voting its proxies for certain closed-end funds whose shares the Fund owns. The instruction forms are available at http://highincomesecuritiesfund.com. If you would like to receive an email notification when the Fund seeks proxy voting instructions for a closed-end fund whose shares it owns, please email us at proxyinfo@highincomesecuritiesfund.com.

Sincerely yours,

Phillip Goldstein

Chairman

2

High Income Securities Fund

$20,000

J

J

$17,500

J

J

J

$15,000

J

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$12,500

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JB

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$15,939 (High Income Securities Fund)

$11,574

(ICE BofA Merrill Lynch 6 Month Treasury Bill Index)

This chart assumes an initial gross investment of $10,000 made on 2/28/2014.

Effective after the close of business on July 23, 2018, the Fund became internally managed and did not pay any management fees for the year ended August 31, 2023. Accordingly, the information presented in this report with respect to the actions and results of the Fund before July 23, 2018 are not material in making any conclusions as to the future performance of the Fund.

Past Performance at a glance (unaudited)

Average annual total returns for the periods ended 2/29/2024

6 month

Net assets value returns

(not annualized)

1 year

5 years

10 years

High Income Securities Fund

5.25%

8.78%

5.03%

4.77%

Market price returns

High Income Securities Fund

6.06%

12.06%

4.33%

5.44%

Index returns

ICE BofA Merrill Lynch 6 Month Treasury Bill Index

2.78%

5.37%

2.12%

1.48%

Share Price as of 2/29/2024

Net asset value

$7.44

Market price

$6.77

The graph and table do not reflect the deduction of taxes that a shareholder would pay on fund distributions or the sale of fund shares.

3

High Income Securities Fund

Generally, the Fund invests in securities of discounted shares of income-orientedclosed-end investment companies, business development companies and Special Purpose Acquisition Vehicles.

Past performance does not predict future performance. The return and value of an investment will fluctuate so that an investor's share, when sold, may be worth more or less than their original cost. The Fund's common stock net asset value ("NAV") return assumes, for illustration only, that dividends and other distributions, if any, were reinvested at the NAV on the ex-dividend date for dividends and other distributions. The Fund's common stock market price returns assume that all dividends and other distributions, if any, were reinvested at prices obtained under the Fund's Dividend Reinvestment Plan (which was terminated on September 12, 2018) for dividends and other distributions payable through September 11, 2018 and reinvested at the lower of the NAV or the closing market price on the ex-dividend date for dividends and other distributions payable after September 11, 2018, and does not account for taxes.

Portfolio composition as of 2/29/2024 (unaudited)(1)

% of

Value

Cost

Net Assets

Closed-End Funds

$ 64,059,296

$ 64,368,969

49.10%

Business Development Companies

21,174,614

22,114,862

16.23

Special Purpose Acquisition Vehicles

19,905,753

19,510,373

15.26

Money Markets

10,438,076

10,438,076

8.00

Preferred Stocks

11,090,487

15,729,983

8.50

Other Common Stocks

915,565

2,122,360

0.70

Liquidating Trust

850,682

904,767

0.65

Corporate Obligations

592,705

1,006,474

0.45

Exchange Traded Funds

456,863

441,587

0.35

Warrants

41,049

122,158

0.03

Rights

20,274

25,868

0.02

Total Investments

$129,545,364

$136,785,477

99.30%

Assets in Excess of Other Liabilities

910,545

0.70

Total Net Assets

$130,455,909

100.00%

(1) As a percentage of net assets.

The following table represents the Fund's investments categorized by country of risk as of February 29, 2024:

Country

% of Net Assets

United States

88.23%

Cayman Islands

10.62%

Ireland

0.45%

99.30%

Liabilities in Excess of Other Assets

0.70%

100.00%

4

High Income Securities Fund

Portfolio of investments-February 29, 2024 (unaudited)

Shares

Value

INVESTMENT COMPANIES-65.33%

Business Development Companies-16.23%

Barings BDC, Inc.

192,889

$ 1,890,312

CION Investment Corp.

617,720

6,659,022

FS KKR Capital Corp.

374,220

7,065,274

Logan Ridge Finance Corp.

81,300

1,808,925

PhenixFIN Corp. (a)

19,193

860,109

Portman Ridge Finance Corp.

157,289

2,890,972

21,174,614

Closed-EndFunds-49.10%

AllianceBernstein National Municipal Income Fund, Inc.

64,176

698,876

Bancroft Fund Ltd.

13,721

212,264

BlackRock California Municipal Income Trust

144,271

1,695,184

Blackstone Strategic Credit Fund

60,774

714,095

BNY Mellon Municipal Income, Inc.

622,204

4,115,879

BNY Mellon Strategic Municipal Bond Fund, Inc.

291,157

1,685,799

BNY Mellon Alcentra Global Credit Income 2024 Target Term Fund, Inc.

67,021

568,338

Carlyle Credit Income Fund

111,472

886,202

ClearBridge Energy Midstream Opportunity Fund, Inc.

87,663

3,260,186

ClearBridge MLP & Midstream Fund, Inc.

68,796

2,899,751

ClearBridge MLP & Midstream Total Return Fund, Inc.

41,239

1,583,578

Destra Multi-Alternative Fund

161,097

1,272,666

DWS Municipal Income Trust

1,174,528

10,500,281

DWS Strategic Municipal Income Trust

171,491

1,509,121

Eaton Vance New York Municipal Bond Fund

281,569

2,787,533

Ellsworth Growth and Income Fund Ltd.

65,128

524,280

Federated Hermes Premier Municipal Income Fund

2,970

32,878

First Trust High Yield Opportunities 2027 Term Fund

54,916

804,519

First Trust MLP and Energy Income Fund

9,498

82,538

Herzfeld Caribbean Basin Fund, Inc.

1,232

3,216

Highland Income Fund

332,526

2,101,564

Invesco High Income 2024 Target Term Fund

123,227

931,596

MFS High Yield Municipal Trust

764,756

2,500,752

MFS Investment Grade Municipal Trust

245,951

1,844,633

MFS Special Value Trust

358

1,547

Miller/Howard High Dividend Fund

46,070

488,803

Morgan Stanley Emerging Markets Debt Fund, Inc.

41,607

298,738

The accompanying notes are an integral part of these financial statements.

5

High Income Securities Fund

Portfolio of investments-February 29, 2024 (unaudited)

Shares

Value

INVESTMENT COMPANIES-(continued)

Closed-EndFunds-(continued)

Morgan Stanley Emerging Markets Domestic Debt Fund, Inc.

100,365

$

469,708

Neuberger Berman Municipal Fund, Inc.

68,397

708,935

Neuberger Berman Next Generation Connectivity Fund, Inc.

397,605

4,715,596

New America High Income Fund, Inc.

150,875

1,096,861

Nuveen Multi-Asset Income Fund

20,588

248,909

Nuveen Preferred & Income Term Fund

19,447

368,910

NXG NextGen Infrastructure Income Fund

41,521

1,469,843

PGIM Global High Yield Fund, Inc.

88,779

1,033,388

PGIM Short Duration High Yield Opportunities Fund

11,503

174,846

Principal Real Estate Income Fund

197,931

1,993,165

Saba Capital Income & Opportunities Fund

231,408

1,691,592

Tortoise Energy Independence Fund, Inc.

49,741

1,532,520

Tortoise Power and Energy Infrastructure Fund, Inc.

92,081

1,340,699

Virtus Convertible & Income 2024 Target Term Fund

39,523

347,802

Virtus Total Return Fund, Inc.

518,376

2,742,209

Western Asset Global Corporate Defined Opportunity Fund, Inc.

174

2,203

Western Asset Intermediate Muni Fund, Inc.

14,866

117,293

64,059,296

Total Investment Companies (Cost $86,483,831)

85,233,910

Shares/Units

EXCHANGE TRADED FUNDS-0.35%

Horizon Kinetics Spac Active ETF

4,700

456,863

Total Exchange Traded Funds (Cost $441,587)

456,863

SPECIAL PURPOSE ACQUISITION VEHICLES-15.26%

99 Acquisition Group, Inc. (a)

151,650

1,557,446

Ai Transportation Acquisition Corp. (a)(e)

10,000

102,800

Ai Transportation Acquisition Corp. (a)(e)

35,269

361,155

AP Acquisition Corp. (a)(e)

82,500

924,825

Ares Acquisition Corp. II (a)(e)

60,015

631,958

Bowen Acquisition Corp. (a)(e)

14,216

147,387

Cartesian Growth Corp. II (a)(e)

50,000

552,000

Colombier Acquisition Corp. II (a)(e)

1

10

Colombier Acquisition Corp. II (a)(e)

12,667

4,813

The accompanying notes are an integral part of these financial statements.

6

High Income Securities Fund

Portfolio of investments-February 29, 2024 (unaudited)

Shares/Units

Value

SPECIAL PURPOSE ACQUISITION VEHICLES-(continued)

Colombier Acquisition Corp. II (a)(e)

38,001

$

387,230

EVe Mobility Acquisition Corp. (a)(e)

40,963

445,272

Feutune Light Acquisition Corp. (a)

50,000

545,500

Four Leaf Acquisition Corp. (a)

41,431

439,997

Global Lights Acquisition Corp. (a)(e)

192,000

1,948,799

Haymaker Acquisition Corp. 4 (a)(e)

129,016

1,336,607

Inflection Point Acquisition Corp. II (a)(e)

217,023

2,265,720

Investcorp Europe Acquisition Corp. I (a)(e)

95,068

1,059,058

Legato Merger Corp. III (a)(e)

40,197

405,588

Nabors Energy Transition Corp. II (a)(e)

58,563

611,983

Patria Latin American Opportunity Acquisition Corp. (a)(e)

12,631

142,351

Quetta Acquisition Corp. (a)

102,660

1,045,079

Screaming Eagle Acquisition Corp. (a)(e)

233,798

2,492,286

TG Venture Acquisition Corp. (a)(b)

190,793

2,113,986

Trailblazer Merger Corp. I (a)

36,458

383,903

Total Special Purpose Acquisition Vehicles (Cost $19,510,373)

19,905,753

Shares

OTHER COMMON STOCKS-0.70%

Real Estate Investment Trusts-0.70%

NexPoint Diversified Real Estate Trust

144,639

915,565

Total Other Common Stocks (Cost $2,122,360)

915,565

PREFERRED STOCKS-8.50%

Business Development Companies-4.74%

OFS Credit Co., Inc.

60,000

1,380,000

SuRo Capital Corp.

200,000

4,806,000

6,186,000

Closed-EndFunds-1.51%

XAI Octagon Floating Rate Alternative Income Term Trust

80,000

1,972,624

Real Estate Investment Trusts-2.19%

Brookfield DTLA Fund Office Trust Investor, Inc., 7.625% (a)

1,615

129

Cedar Realty Trust, Inc.- Series C, 6.500%

101,456

1,412,268

NexPoint Diversified Real Estate Trust-Series A, 5.500%

94,082

1,439,455

2,851,852

The accompanying notes are an integral part of these financial statements.

7

High Income Securities Fund

Portfolio of investments-February 29, 2024 (unaudited)

Shares

Value

PREFERRED STOCKS-(continued)

Real Estate Operations and Development-0.06%

Harbor Custom Development, Inc-Series A, 8.000% (a)

131,166

$

80,011

Retail-CatalogShopping-0.00%

iMedia Brands, Inc. (b)

27,802

0

Total Preferred Stocks (Cost $15,729,983)

11,090,487

LIQUIDATING TRUSTS-0.65%

Copper Property CTL Pass Through Trust

83,811

850,682

Total Liquidating Trusts (Cost $904,767)

850,682

Principal Amount

CORPORATE OBLIGATIONS-0.46%

Lamington Road DAC

8.000%, 2121-04-07 (b)(c)(d)(e)

8,072,998

322,920

14.000%, 2121-04-07 (b)(c)(d)(e)

519,816

269,785

Total Corporate Obligations (Cost $1,006,474)

592,705

Shares

RIGHTS-0.02% (a)

Lakeshore Acquisition II Corp. (a)(e)

59,500

15,470

Nocturne Acquisition Corp. (a)(e)

40,000

4,804

Total Rights (Cost $25,868)

20,274

WARRANTS-0.03% (a)

Andretti Acquisition Corp. (a)(e)

Expiration: March 2028

Exercise Price: $11.50

25,000

5,753

AtlasClear Holdings, Inc. (a)

Expiration: October 2028

Exercise Price: $11.50

33,000

1,320

Ault Disruptive Technologies Corp. (a)

Expiration: June 2028

Exercise Price: $11.50

48,000

389

Cartesian Growth Corp. II (a)(e)

Expiration: July 2028

Exercise Price: $11.50

33,333

4,500

Churchill Capital Corp. VII (a)

Expiration: February 2028

Exercise Price: $11.50

11,761

3,999

The accompanying notes are an integral part of these financial statements.

8

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Disclaimer

High Income Securities Fund published this content on 25 April 2024 and is solely responsible for the information contained therein. Distributed by Public, unedited and unaltered, on 25 April 2024 19:29:39 UTC.