HFRO / Highland Funds I - Highland Opportunities and Income Fund - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

Highland Funds I - Highland Opportunities and Income Fund
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Mga Batayang Estadistika
CIK 1710680
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Highland Funds I - Highland Opportunities and Income Fund
SEC Filings (Chronological Order)
Halaman ini menyediakan daftar lengkap dan kronologis dari Pengajuan SEC, tidak termasuk pengajuan kepemilikan yang kami sediakan di tempat lain.
May 7, 2025 DEF 14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒       Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to Sec.

March 13, 2025 EX-99.(A)(5)(5)

Highland Opportunities and Income Fund (HFRO) Provides Details on Results of Oversubscribed Tender and Exchange Offer

Highland Opportunities and Income Fund SC TO-I/A Exhibit 99.(a)(5)(5) Highland Opportunities and Income Fund (HFRO) Provides Details on Results of Oversubscribed Tender and Exchange Offer DALLAS, March 12, 2025 - The Highland Opportunities and Income Fund (NYSE:HFRO) (“HFRO” or the “Fund”) today announced the final results of its tender and exchange offer (the “Exchange Offer”) to exchange common

March 13, 2025 SC TO-I/A

As filed with the Securities and Exchange Commission on March 12, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. 3) Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities E

As filed with the Securities and Exchange Commission on March 12, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

March 6, 2025 EX-99.(A)(5)(4)

Highland Opportunities and Income Fund (HFRO) Provides Details on Results of Oversubscribed Tender and Exchange Offer

Highland Opportunities & Income Fund SC TO-I Exhibit 99.(a)(5)(4) Highland Opportunities and Income Fund (HFRO) Provides Details on Results of Oversubscribed Tender and Exchange Offer DALLAS, March 5, 2025 - The Highland Opportunities and Income Fund (NYSE:HFRO) (“HFRO” or the “Fund”) today announced the details of its tender and exchange offer (the “Exchange Offer”) to exchange common shares (the

March 6, 2025 SC TO-I/A

As filed with the Securities and Exchange Commission on March 6, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. 2) Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Ex

As filed with the Securities and Exchange Commission on March 6, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

March 5, 2025 SC TO-I/A

As filed with the Securities and Exchange Commission on March 5, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. 1) Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Ex

As filed with the Securities and Exchange Commission on March 5, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

March 5, 2025 EX-99.(D)(14)

SUB-ADMINISTRATION AGREEMENT

Highland Opportunities and Income Fund SC TO-I/A Exhibit 99(d)(14) SUB-ADMINISTRATION AGREEMENT THIS SUB-ADMINISTRATION AGREEMENT (this “Agreement”) is made as of the 23rd day of July, 2018 (the “Effective Date”), by and between Highland Capital Management Fund Advisors, L.

March 5, 2025 EX-99.(A)(5)(3)

Highland Opportunities and Income Fund (HFRO) Announces Completion of Oversubscribed Tender and Exchange Offer

EX-99.(A)(5)(3) 2 ex99-a53.htm PRESS RELEASE Highland Opportunities and Income Fund SC TO-I/A Exhibit 99.(a)(5)(3) Highland Opportunities and Income Fund (HFRO) Announces Completion of Oversubscribed Tender and Exchange Offer DALLAS, March 5, 2025 - The Highland Opportunities and Income Fund (NYSE:HFRO) (“HFRO” or the “Fund”) today announced the successful completion of its tender and exchange off

March 5, 2025 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 HIGHLAND OPPORTUNITIES AND INCOME FUND (Exact n

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 HIGHLAND OPPORTUNITIES AND INCOME FUND (Exact name of registrant as specified in its charter) Massachusetts 456245636 (State of incorporation or organization) (I.R.S. Employer Identification No.) 3

February 3, 2025 EX-99.(A)(1)(I)

OFFER TO EXCHANGE Highland Opportunities and Income Fund 300 Crescent Court Suite 700 Dallas, Texas 75201 OFFER TO EXCHANGE COMMON SHARES, PAR VALUE $0.001 PER SHARE, 5.375% SERIES B CUMULATIVE PREFERRED SHARES, PAR VALUE $0.001 AND LIQUIDATION PREFE

Highland Opportunities & Income Fund SC TO-I Exhibit 99.(a)(1)(i) OFFER TO EXCHANGE Highland Opportunities and Income Fund 300 Crescent Court Suite 700 Dallas, Texas 75201 OFFER TO EXCHANGE COMMON SHARES, PAR VALUE $0.001 PER SHARE, FOR 5.375% SERIES B CUMULATIVE PREFERRED SHARES, PAR VALUE $0.001 AND LIQUIDATION PREFERENCE $25.00 PER SHARE Dated February 3, 2025 THIS EXCHANGE OFFER WILL EXPIRE AT

February 3, 2025 EX-99.(A)(1)(IV)

Offer to Exchange for Preferred Shares Highland Opportunities and Income Fund Up to $100 Million in Value of its Common Shares At a Purchase Price of $10.00 per Share

Highland Opportunities & Income Fund SC TO-I Exhibit 99.(a)(1)(iv) Offer to Exchange for Preferred Shares by Highland Opportunities and Income Fund Up to $100 Million in Value of its Common Shares At a Purchase Price of $10.00 per Share THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 5:00 P.M., NEW YORK CITY TIME, ON MARCH 4, 2025, UNLESS THE OFFER IS EXTENDED OR TERMINATED (SUCH

February 3, 2025 SC TO-I

As filed with the Securities and Exchange Commission on February 3, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. __) Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securitie

As filed with the Securities and Exchange Commission on February 3, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

February 3, 2025 EX-99.(A)(5)(1)

Highland Opportunities and Income Fund (HFRO) Announces Commencement of Tender and Exchange Offer

Highland Opportunities & Income Fund SC TO-I Exhibit 99.(a)(5)(1) Highland Opportunities and Income Fund (HFRO) Announces Commencement of Tender and Exchange Offer DALLAS, February 3, 2025 - The Highland Opportunities and Income Fund (NYSE:HFRO) (“HFRO” or the “Fund”) today announced the commencement of a tender and exchange offer (the “Exchange Offer”) for common shares (the “Shares”) in exchange

February 3, 2025 EX-99.(A)(1)(II)

Letter of Transmittal To Tender Common Shares Pursuant to the Offer to Exchange Dated February 3, 2025 Highland Opportunities and Income Fund COMMON SHARES, PAR VALUE $0.001 PER SHARE, 5.375% SERIES B CUMULATIVE PREFERRED SHARES, PAR VALUE $0.001 AND

Highland Opportunities & Income Fund SC TO-I Exhibit 99.(a)(1)(ii) Letter of Transmittal To Tender Common Shares Pursuant to the Offer to Exchange Dated February 3, 2025 by Highland Opportunities and Income Fund Of COMMON SHARES, PAR VALUE $0.001 PER SHARE, FOR 5.375% SERIES B CUMULATIVE PREFERRED SHARES, PAR VALUE $0.001 AND LIQUIDATION PREFERENCE $25.00 PER SHARE THE OFFER AND WITHDRAWAL RIGHTS

February 3, 2025 EX-99.(A)(1)(III)

Offer to Exchange for Preferred Shares Highland Opportunities and Income Fund Up to $100 Million in Value of its Common Shares At a Purchase Price of $10.00 per Share

Highland Opportunities & Income Fund SC TO-I Exhibit 99.(a)(1)(iii) Offer to Exchange for Preferred Shares by Highland Opportunities and Income Fund Up to $100 Million in Value of its Common Shares At a Purchase Price of $10.00 per Share THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 5:00 P.M., NEW YORK CITY TIME, ON MARCH 4, 2024, UNLESS THE OFFER IS EXTENDED OR TERMINATED (SUCH

February 3, 2025 EX-99.(D)(8)

HIGHLAND OPPORTUNITIES AND INCOME FUND STATEMENT OF PREFERENCES OF 5.375% SERIES B CUMULATIVE PREFERRED SHARES

Highland Opportunities & Income Fund SC TO-I Exhibit 99.(d)(8) HIGHLAND OPPORTUNITIES AND INCOME FUND STATEMENT OF PREFERENCES OF 5.375% SERIES B CUMULATIVE PREFERRED SHARES Highland Opportunities and Income Fund, a Massachusetts business trust (the “Trust”), hereby certifies that: FIRST: The Board of Trustees of the Trust, at a meeting duly convened and held on April 11, 2019, (i) pursuant to aut

February 3, 2025 EX-FILING FEES

Calculation of Filing Fee Table SC TO-I (Form Type) HIGHLAND OPPORTUNITIES AND INCOME FUND (Exact Name of Registrant as Specified in its Charter) Table 1: Transaction Valuation Transaction Valuation Fee rate Amount of Filing Fee Fees to Be Paid $100,

Highland Opportunities & Income Fund SC TO-I Exhibit 107 Calculation of Filing Fee Table SC TO-I (Form Type) HIGHLAND OPPORTUNITIES AND INCOME FUND (Exact Name of Registrant as Specified in its Charter) Table 1: Transaction Valuation Transaction Valuation Fee rate Amount of Filing Fee Fees to Be Paid $100,000,000(1) 0.

February 3, 2025 EX-99.(A)(5)(2)

Highland Opportunities & Income Fund SC TO-I

Highland Opportunities & Income Fund SC TO-I Exhibit 99.(a)(5)(2)

January 2, 2025 EX-99.(A)(III)

FIRST AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST HIGHLAND INCOME FUND

FIRST AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST OF HIGHLAND INCOME FUND To the Secretary of State of Commonwealth of Massachusetts It is hereby stated that: 1.

January 2, 2025 EX-99.(A)(VI)

FOURTH AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST HIGHLAND INCOME FUND

FOURTH AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST OF HIGHLAND INCOME FUND To the Secretary of State of Commonwealth of Massachusetts It is hereby stated that: 1.

January 2, 2025 EX-99.(A)(V)

THIRD AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST OF HIGHLAND INCOME FUND

THIRD AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST OF HIGHLAND INCOME FUND To the Secretary of the Commonwealth of Massachusetts It is hereby stated that: 1, This document constitutes an amendment, dated December 21, 2021, to the Third Amended and Restated Agreement and Declaration of Trust, dated July 26, 2019 (hereinafter called the “Declaration of Trust”) of Highland Income Fund.

January 2, 2025 EX-99.(S)(III)

HIGHLAND INCOME FUND HIGHLAND GLOBAL ALLOCATION FUND POWER OF ATTORNEY

HIGHLAND INCOME FUND HIGHLAND GLOBAL ALLOCATION FUND POWER OF ATTORNEY Highland Income Fund and Highland Global Allocation Fund (collectively, the “Trusts”) and the undersigned Trustee constitutes and appoints each of James Dondero, Frank Waterhouse, Will Mabry, Dustin Norris, and Stephanie Vitiello (with full power to each of them to act alone) his/her true and lawful attorney-in-fact and agent,

January 2, 2025 EX-99.(B)

THIRD AMENDED AND RESTATED BYLAWS HIGHLAND INCOME FUND (Dated as of December 21, 2021)

THIRD AMENDED AND RESTATED BYLAWS OF HIGHLAND INCOME FUND (Dated as of December 21, 2021) DEFINITIONS “Independent Trustee” shall mean a Trustee that is not an “interested person” as defined in Section 2(a)(19) of the 1940 Act.

January 2, 2025 EX-99.(A)(IV)

SECOND AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST HIGHLAND INCOME FUND

SECOND AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST OF HIGHLAND INCOME FUND To the Secretary of State of Commonwealth of Massachusetts It is hereby stated that: 1.

January 2, 2025 EX-99.(A)(I)

HIGHLAND INCOME FUND THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST

HIGHLAND INCOME FUND THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST THIS THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST made on this 26th day of July, 2019 by the Trustees hereunder, amending and restating the Second Amended and Restated Agreement and Declaration of Trust made on the 25th of September, 2017: WHEREAS, pursuant to Section 8 of Article IX of the Second A

January 2, 2025 EX-99.(A)(II)

HIGHLAND INCOME FUND STATEMENT OF PREFERENCES 5.375% SERIES A CUMULATIVE PREFERRED SHARES

Exhibit (a)(2) EXECUTION VERSION HIGHLAND INCOME FUND STATEMENT OF PREFERENCES OF 5.

January 2, 2025 POS EX

As filed with the Securities and Exchange Commission on January 2, 2025

As filed with the Securities and Exchange Commission on January 2, 2025 Securities Act File No.

December 11, 2024 SC TO-C

As filed with the Securities and Exchange Commission on December 11, 2024 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act Of 1934 Highland

As filed with the Securities and Exchange Commission on December 11, 2024 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

December 11, 2024 EX-99.1

HIGHLAND OPPORTUNITIES AND INCOME FUND HFRO Snapshot Highland Opportunities and Income Fund (HFRO) is a Overview closed-end, non-diversified management investment company focused on delivering attractive returns Ticker HFRO through interest income an

EX-99.1 2 d87890dex991.htm EX-99.1 Exhibit 99.1(a) Q3 2024 INVESTOR PRESENTATION Highland Opportunities and Income Fund December 2024 HIGHLAND OPPORTUNITIES AND INCOME FUND HFRO Snapshot Highland Opportunities and Income Fund (HFRO) is a Overview closed-end, non-diversified management investment company focused on delivering attractive returns Ticker HFRO through interest income and capital apprec

November 25, 2024 SC TO-C

As filed with the Securities and Exchange Commission on November 25, 2024 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act Of 1934 Highland

As filed with the Securities and Exchange Commission on November 25, 2024 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

November 25, 2024 EX-99.1(A)

###

Exhibit 99.1A Highland Opportunities and Income Fund (HFRO) Announces Tender Offer for Common Shares in Exchange for up to $100 Million in Preferred Shares DALLAS, November 25, 2024 - The Highland Opportunities and Income Fund (NYSE:HFRO) (“HFRO” or the “Fund”) today announced its plan to conduct an issuer tender offer pursuant to Rule 13e-4 under the Securities Exchange Act of 1934 for its common

July 24, 2024 424B3

HIGHLAND OPPORTUNITIES AND INCOME FUND (the “Fund”) Supplement dated July 24, 2024 to the Fund’s Statement of Additional Information (the “SAI”), dated July 1, 2019, as supplemented from time to time

HIGHLAND OPPORTUNITIES AND INCOME FUND (the “Fund”) Supplement dated July 24, 2024 to the Fund’s Statement of Additional Information (the “SAI”), dated July 1, 2019, as supplemented from time to time This supplement provides new and additional information beyond that contained in the SAI and should be read in conjunction with the SAI.

May 17, 2024 DEF 14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒       Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to Sec.

August 15, 2023 NPORT-EX

Collateral Pledged

CONSOLIDATED INVESTMENT PORTFOLIO (unaudited) As of September 30, 2022 Highland Income Fund Shares Value ($) Common Stocks — 56.

August 15, 2023 NPORT-EX

Security Type

HTML INVESTMENT PORTFOLIO (unaudited) As of March 31, 2023 Highland Income Fund Shares Value ($) Common Stocks — 62.

May 4, 2023 CORRESP

2

CORRESP May 4, 2023 VIA EDGAR AND EMAIL U.S. Securities and Exchange Commission Division of Investment Management Office of Disclosure and Review 100 F Street, NE Washington, DC 20549 Attention: Ms. Megan Miller Re: NexPoint Funds I (File No. 811-21866) Highland Income Fund (File No. 811-23268) Highland Global Allocation Fund (File No. 811-23369) NexPoint Real Estate Strategies Fund (File No. 811-

May 2, 2023 DEF 14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

Highland Income Fund SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to Sec.

March 10, 2023 424B3

HIGHLAND INCOME FUND (the “Fund”) Supplement dated March 10, 2023 to the Fund’s Statement of Additional Information (the “SAI”), dated June 26, 2019, as supplemented from time to time

Highland Income Fund HIGHLAND INCOME FUND (the “Fund”) Supplement dated March 10, 2023 to the Fund’s Statement of Additional Information (the “SAI”), dated June 26, 2019, as supplemented from time to time This supplement provides new and additional information beyond that contained in the SAI and should be read in conjunction with the SAI.

November 29, 2022 NPORT-EX

Collateral Pledged

CONSOLIDATED INVESTMENT PORTFOLIO (unaudited) As of September 30, 2022 Highland Income Fund Shares Value ($) Common Stocks — 56.

September 26, 2022 424B3

HIGHLAND INCOME FUND (the “Fund”) Supplement dated September 26, 2022 to the Fund’s Prospectus and Statement of Additional Information (“SAI”), each dated June 26, 2019, as supplemented from time to time

HIGHLAND INCOME FUND (the ?Fund?) Supplement dated September 26, 2022 to the Fund?s Prospectus and Statement of Additional Information (?SAI?), each dated June 26, 2019, as supplemented from time to time This supplement provides new and additional information beyond that contained in the Prospectus and the SAI and should be read in conjunction with the Prospectus and the SAI.

May 31, 2022 NPORT-EX

Expiration Date

NPORT-EX 2 HighlandIncomeFundSchF.htm SCHEDULE F CONSOLIDATED INVESTMENT PORTFOLIO (unaudited) As of March 31, 2022 Highland Income Fund Shares Value ($) Common Stocks — 60.9% COMMUNICATION SERVICES — 1.2% 97,600 Telesat (a) 1,610,400 96,700 Telesat, Class B (a) 1,595,550 27,134 TerreStar Corporation (a)(b)(c)(d) 8,916,232 12,122,182 CONSUMER DISCRETIONARY — 0.0% 1,450 Toys ‘R’ Us (a)(b)(c) 31,683

May 2, 2022 424B3

HIGHLAND INCOME FUND (the “Fund”) Supplement dated May 2, 2022 to the Fund’s Statement of Additional Information (the “SAI”), dated June 26, 2019, as supplemented from time to time

424B3 1 d327626d424b3.htm HIGHLAND INCOME FUND HIGHLAND INCOME FUND (the “Fund”) Supplement dated May 2, 2022 to the Fund’s Statement of Additional Information (the “SAI”), dated June 26, 2019, as supplemented from time to time This supplement provides new and additional information beyond that contained in the SAI and should be read in conjunction with the SAI. Capitalized terms and certain other

March 28, 2022 DEF 14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to Sec.

January 13, 2022 424B3

HIGHLAND INCOME FUND (the “Fund”) Supplement dated January 13, 2022 to the Fund’s Statement of Additional Information (the “SAI”), dated June 26, 2019, as supplemented from time to time

HIGHLAND INCOME FUND (the ?Fund?) Supplement dated January 13, 2022 to the Fund?s Statement of Additional Information (the ?SAI?), dated June 26, 2019, as supplemented from time to time This supplement provides new and additional information beyond that contained in the SAI and should be read in conjunction with the SAI.

December 30, 2021 EX-3.1

Third Amendment to the Third Amended and Restated Agreement and Declaration of Trust of Highland Income Fund, effective as of December 21, 2021

Exhibit 3.1 THIRD AMENDMENT TO THE THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST OF HIGHLAND INCOME FUND To the Secretary of the Commonwealth of Massachusetts It is hereby stated that: 1. This document constitutes an amendment, dated December 21, 2021, to the Third Amended and Restated Agreement and Declaration of Trust, dated July 26, 2019 (hereinafter called the ?Declaration of T

December 30, 2021 EX-3.2

Third Amended and Restated Bylaws of Highland Income Fund, effective as of December 21, 2021

Exhibit 3.2 THIRD AMENDED AND RESTATED BYLAWS OF HIGHLAND INCOME FUND (Dated as of December 21, 2021) DEFINITIONS ?Independent Trustee? shall mean a Trustee that is not an ?interested person? as defined in Section 2(a)(19) of the 1940 Act. ?Proposed Nominee? shall have the meaning set forth in Section 10.10 of these Bylaws ?Proposed Nominee Associated Person? of any Proposed Nominee shall mean (A)

December 30, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

8-K 1 d97886d8k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 30, 2021 (December 21, 2021) HIGHLAND INCOME FUND (Exact Name of Registrant as Specified in Charter) MASSACHUSETTS 811-23268 45-6245636 (State or Othe

November 29, 2021 NPORT-EX

Security Type

NPORT-EX 2 HighlandIncomeFundSchF.htm SCHEDULE F CONSOLIDATED INVESTMENT PORTFOLIO (unaudited) As of September 30, 2021 Highland Income Fund Shares Value ($) Common Stocks — 42.2% COMMUNICATION SERVICES — 7.9% 96,700 Loral Space & Communications, Inc. 4,159,067 502,161 Metro-Goldwyn-Mayer, Inc. (a)(b) 66,159,963 27,134 TerreStar Corporation (a)(b)(c)(d) 9,163,966 79,482,996 CONSUMER DISCRETIONARY

November 3, 2021 CORRESP

1

CORRESP 1 filename1.htm November 3, 2021 VIA EDGAR AND EMAIL U.S. Securities and Exchange Commission Division of Investment Management 100 F Street, N.E. Washington, D.C. 20549 Attention: Ms. Christina DiAngelo Fettig Re: Highland Funds I (File No. 811-21866), Highland Income Fund (File No. 811-23268), NexPoint Real Estate Strategies Fund (File No. 811-23129), and NexPoint Strategic Opportunities

October 13, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

October 13, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

September 30, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

September 28, 2021 SC 13D/A

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND / GOLDSTEIN PHILLIP Activist Investment

SC 13D/A 1 fp0069014sc13da.htm SCHEDULE 13D/A DATE OF EVENT WHICH REQUIRES FILING OF THIS STATEMENT: 09/27/2021 1. NAME OF REPORTING PERSON Phillip Goldstein 2. CHECK THE BOX IF MEMBER OF A GROUP a[] b[] 3. SEC USE ONLY 4. SOURCE OF FUNDS WC 5. CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEMS 2(d) AND 2(e) [] 6. CITIZENSHIP OR PLACE OF ORGANIZATION USA 7. SOLE VOTING POWE

September 28, 2021 EX-99.7.A

Phillip Goldstein, 250 Pehle Avenue, Suite 708, Saddle Brook, NJ 07663 (201) 881-7111 // Fax: (201) 556-0097 // [email protected]

Phillip Goldstein, 250 Pehle Avenue, Suite 708, Saddle Brook, NJ 07663 (201) 881-7111 // Fax: (201) 556-0097 // pgoldstein@bulldoginvestors.

September 24, 2021 SC TO-C

As filed with the Securities and Exchange Commission on September 24, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act Of 1934 Highland

As filed with the Securities and Exchange Commission on September 24, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

September 24, 2021 EX-99.2

Outbound Message and Answering Machine Script

Exhibit 99.2 HIGHLAND INCOME FUND CALL CENTER OUTBOUND CALLING SCRIPT Hello, my name is (CSR FULL NAME). May I please speak with (SHAREHOLDER?S FULL NAME)? (Repeat the greeting if necessary) I am calling on a recorded line regarding your current investment in the Highland Income Fund. Materials were sent to you for the upcoming Adjourned Special Meeting of Shareholders scheduled to take place on O

September 24, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

September 24, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

September 24, 2021 EX-99.1

Press Release, dated September 24, 2021

Exhibit 99.1 Highland Income Fund (HFRO) Announces Supplement to Proxy Statement, Adjourns Special Meeting of Shareholders to Allow Review of Supplemented Proxy Special Meeting of Shareholders Adjourned to October 15, 2021, to Allow Shareholders to Review Latest Supplement to Proxy Statement DALLAS ? September 24, 2021 ? The Highland Income Fund (NYSE: HFRO) (?HFRO? or the ?Fund?), a closed-end fu

September 23, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

September 3, 2021 SC TO-C

As filed with the Securities and Exchange Commission on September 3, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act Of 1934 Highland

As filed with the Securities and Exchange Commission on September 3, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

September 3, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

September 3, 2021 EX-99.1

300 CRESCENT COURT, SUITE 700 | DALLAS, TEXAS 75201

Exhibit 99.1 September 3, 2021 Kathryn Cohen Executive Director Institutional Shareholder Services 702 King Farm Boulevard, Suite 400 Rockville, MD 20850 Dear Ms. Cohen, I am writing in regard to the August 11, 2021 report (the ?Report?) issued by Institutional Shareholder Services, Inc. (?ISS?) on the Highland Income Fund (NYSE: HFRO) (?HFRO? or the ?Fund?), a closed-end fund managed by Highland

September 2, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 26, 2021 PX14A6G

Thomas J. Herzfeld Advisors, Inc. 119 Washington Ave., Suite 504 Miami Beach, FL 33139

Notice of Exempt Solicitation Pursuant to Rule 14a-103 Name of the Registrant: Highland Income Fund (HFRO) Name of persons relying on exemption: Thomas J.

August 24, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 20, 2021 SC TO-C

As filed with the Securities and Exchange Commission on August 20, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act Of 1934 Highland In

As filed with the Securities and Exchange Commission on August 20, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 20, 2021 EX-99.1

SHAREHOLDER ACTIVIST TARGETS YOUR FUND

Exhibit 99.1 August 20, 2021 DEAR FELLOW SHAREHOLDER: The Highland Income Fund (?Fund?) special meeting of Shareholders, originally scheduled for August 20, 2021 (the ?Special Meeting?), has been adjourned until September 24, 2021. Your Fund?s Board of Trustees believes that an adjournment is in the best interest of the Fund and its shareholders in order to (i) permit the Fund to continue its ongo

August 20, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 20, 2021 EX-99.4

The proposed conversion of HFRO to a diversified holding company is contingent upon an affirmative shareholder vote, regulatory approval, and the ability to reconfigure HFRO’s portfolio such that it is no longer an investment company for purposes of

Exhibit 99.4 UPDATED AS OF AUG. 20, 2021 W W W . H F R OC ONV E R S I ON. C OM HFRO CO N V ERSIO N PRO PO SAL Over view of proposal to conver t HFRO into a p u b l icl y tr ad ed D iv er sified H ol d in g Comp an y H I G H L A ND I NC OM E F U ND ( NY S E : H F R O) | AU G U ST 202 1Exhibit 99.4 UPDATED AS OF AUG. 20, 2021 W W W . H F R OC ONV E R S I ON. C OM HFRO CO N V ERSIO N PRO PO SAL Over

August 20, 2021 EX-99.3

HIGHLAND INCOME FUND

HIGHLAND INCOME FUND CALL CENTER OUTBOUND CALLING SCRIPT Exhibit 99.3 Hello, my name is (CSR FULL NAME). May I please speak with (SHAREHOLDER?S FULL NAME)? (Repeat the greeting if necessary) I am calling on a recorded line regarding your current investment in the Highland Income Fund. Materials were sent to you for the upcoming Adjourned Special Meeting of Shareholders scheduled to take place on S

August 20, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 20, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 20, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 20, 2021 EX-99.2

Highland Income Fund (HFRO) Announces Adjournment of Special Meeting of Shareholders Special Meeting of Shareholders Adjourned to September 24, 2021 to Allow Shareholders to Review Recent Updates to Holding Company Conversion Proposal

Exhibit 99.2 Highland Income Fund (HFRO) Announces Adjournment of Special Meeting of Shareholders Special Meeting of Shareholders Adjourned to September 24, 2021 to Allow Shareholders to Review Recent Updates to Holding Company Conversion Proposal DALLAS ? August 20, 2021 ? The Highland Income Fund (NYSE: HFRO) (?HFRO? or the ?Fund?), a closed-end fund managed by Highland Capital Management Fund A

August 18, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definiti

August 18, 2021 EX-99.1

On June 14, 2021, the Highland Income Fund (NYSE: HFRO) (“HFRO” or the “Fund”), a

Table of Contents Exhibit 99.1 INTRODUCTION On June 14, 2021, the Highland Income Fund (NYSE: HFRO) (?HFRO? or the ?Fund?), a closed-end fund managed by Highland Capital Management Fund Advisors, L.P. (the ?Adviser,? ?we,? ?us,? or ?our?), announced a proposal to convert the Fund from a registered investment company to a diversified holding company (the ?Holding Company?). In conjunction with the

August 18, 2021 SC TO-C

As filed with the Securities and Exchange Commission on August 18, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act Of 1934 Highland In

As filed with the Securities and Exchange Commission on August 18, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 17, 2021 SC TO-C

As filed with the Securities and Exchange Commission on August 17, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act Of 1934 Highland In

As filed with the Securities and Exchange Commission on August 17, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 17, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 17, 2021 EX-99.1

Highland Income Fund (HFRO) Receives Approval for Tender Offer as Part of Holding Company Conversion Fund’s Board Approves Tender Offer as Supplement to Conversion Proposal Under Tender Offer, HFRO Will Purchase Up to $50 Million of Common Shares

Exhibit 99.1 Highland Income Fund (HFRO) Receives Approval for Tender Offer as Part of Holding Company Conversion Fund?s Board Approves Tender Offer as Supplement to Conversion Proposal Under Tender Offer, HFRO Will Purchase Up to $50 Million of Common Shares DALLAS ? August 17, 2021 ? The Highland Income Fund (NYSE: HFRO) (?HFRO? or the ?Fund?), a closed-end fund managed by Highland Capital Manag

August 17, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 17, 2021 EX-99.2

HIGHLAND INCOME FUND 2515 McKinney Avenue Suite 1100 Dallas, Texas 75201 (800) 357-9167 SUPPLEMENT NO. 2 TO THE PROXY STATEMENT DATED JULY 9, 2021 FOR THE SPECIAL MEETING OF SHAREHOLDERS TO BE HELD ON AUGUST 20, 2021

Exhibit 99.2 HIGHLAND INCOME FUND 2515 McKinney Avenue Suite 1100 Dallas, Texas 75201 (800) 357-9167 SUPPLEMENT NO. 2 TO THE PROXY STATEMENT DATED JULY 9, 2021 FOR THE SPECIAL MEETING OF SHAREHOLDERS TO BE HELD ON AUGUST 20, 2021 On July 9, 2021, Highland Income Fund (the ?Fund?) mailed to its shareholders a definitive proxy statement for the Fund?s special meeting of shareholders to be held on Au

August 16, 2021 EX-99.2

HIGHLAND INCOME FUND 2515 McKinney Avenue Suite 1100 Dallas, Texas 75201 (800) 357-9167 SUPPLEMENT TO THE PROXY STATEMENT DATED JULY 9, 2021 FOR THE SPECIAL MEETING OF SHAREHOLDERS TO BE HELD ON AUGUST 20, 2021

Exhibit 99.2 HIGHLAND INCOME FUND 2515 McKinney Avenue Suite 1100 Dallas, Texas 75201 (800) 357-9167 SUPPLEMENT TO THE PROXY STATEMENT DATED JULY 9, 2021 FOR THE SPECIAL MEETING OF SHAREHOLDERS TO BE HELD ON AUGUST 20, 2021 On July 9, 2021, Highland Income Fund (the ?Fund?) mailed to its shareholders a definitive proxy statement (the ?Proxy Statement?) for the Fund?s special meeting of shareholder

August 16, 2021 SC TO-C

As filed with the Securities and Exchange Commission on August 13, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO Tender Offer Statement Under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act Of 1934 Highland In

As filed with the Securities and Exchange Commission on August 13, 2021 SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 16, 2021 EX-99.1

Highland Income Fund (HFRO) Announces Tender Offer as Part of Holding Company Conversion Proposal HFRO to Purchase Up to $50 Million of Common Shares Under Proposed Tender Offer, Files Proxy Amendment Updating Conversion Proposal with Tender Offer Te

Exhibit 99.1 Highland Income Fund (HFRO) Announces Tender Offer as Part of Holding Company Conversion Proposal HFRO to Purchase Up to $50 Million of Common Shares Under Proposed Tender Offer, Files Proxy Amendment Updating Conversion Proposal with Tender Offer Terms Adviser Provides Additional Information on Conversion and Updates on Proposal DALLAS ? August 13, 2021 ? The Highland Income Fund (NY

August 16, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

August 13, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check appropriate box: ? Preliminary Proxy Statement ? Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement

July 14, 2021 DEFA14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to Sec.

July 13, 2021 DEFA14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to Sec.

July 9, 2021 DEFA14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to Sec.

July 9, 2021 DEF 14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

Table of Contents SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to Sec.

July 1, 2021 DEFR14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant [ X ] Filed by a Party other than the Registrant [ ] Check the appropriate box: [ ] Preliminary Proxy Statement [ ] Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) [ ] Definitive Proxy Statement [ X ] Definitive Additional Materials [ ] Soliciting Material Pursuant to Sec.

June 16, 2021 DEFA14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

Table of Contents SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to Sec.

June 14, 2021 PRE 14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

Table of Contents SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to Sec.

June 14, 2021 DEF 14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to Sec.

June 14, 2021 DEFA14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to Sec.

June 1, 2021 NPORT-EX

Valuation Technique

CONSOLIDATED INVESTMENT PORTFOLIO (unaudited) As of March 31, 2021 Highland Income Fund Shares Value ($) Common Stocks — 40.

November 30, 2020 NPORT-EX

Valuation Technique

HTML CONSOLIDATED INVESTMENT PORTFOLIO (unaudited) As of September 30, 2020 Highland Income Fund Shares Value ($) Preferred Stock — 35.

October 13, 2020 NPORT-EX

- SCHEDULE F

INVESTMENT PORTFOLIO (unaudited) As of September 30, 2019 Highland Income Fund Principal Amount ($) Value ($) U.

October 13, 2020 NPORT-EX

- SCHEDULE F

INVESTMENT PORTFOLIO (unaudited) As of March 31, 2020 Highland Income Fund Principal Amount ($) Value ($) U.

June 1, 2020 NPORT-EX

Collateral Pledged

INVESTMENT PORTFOLIO (unaudited) As of March 31, 2020 Highland Income Fund Principal Amount ($) Value ($) U.

April 22, 2020 DEF 14A

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND DEF 14A - - FORM DEF 14A

SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant [ X ] Filed by a Party other than the Registrant [ ] Check the appropriate box: [ ] Preliminary Proxy Statement [ ] Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) [X] Definitive Proxy Statement [ ] Definitive Additional Materials [ ] Soliciting Material Pursuant to Sec.

March 17, 2020 NT-NCEN

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND NT-NCEN - - FORM NT-NCEN

Form NT-NCEN SEC FILE NUMBER 811-23268 CUSIP NUMBER 43010E404 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

March 12, 2020 NT-NCSR

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND NT-NCSR - - NT-NCSR

NT-NCSR UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SEC FILE NUMBER 811-23268 CUSIP NUMBER 43010E404 FORM 12b-25 NOTIFICATION OF LATE FILING (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☒ Form N-CSR For Period Ended: December 31, 2019 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐ Transition Report on Form 11

November 29, 2019 NPORT-EX

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND NPORT-EX - - SCHEDULE F

NPORT-EX 2 HighlandIF.htm SCHEDULE F INVESTMENT PORTFOLIO (unaudited) As of September 30, 2019 Highland Income Fund Principal Amount ($) Value ($) U.S. Senior Loans (a) — 57.4% Commercial Services — 3.2% American Traffic Solutions, Inc., 10,102,055 VAR LIBOR USD 3 Month+3.750%, 02/21/25 10,156,758 EmployBridge LLC, 2018 Refinancing Term Loan, 13,485,547 VAR LIBOR USD 3 Month+4.500%, 04/18/25 13,48

July 31, 2019 8-A12B

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND 8-A12B - - HIGHLAND INCOME FUND

HIGHLAND INCOME FUND HIGHLAND INCOME FUND SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 31, 2019 EX-99.(A)(1)

HIGHLAND INCOME FUND THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST

Third Amended and Restated Agreement HIGHLAND INCOME FUND THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST THIS THIRD AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST made on this 26th day of July, 2019 by the Trustees hereunder, amending and restating the Second Amended and Restated Agreement and Declaration of Trust made on the 25th of September, 2017: WHEREAS, pursuant to Se

July 31, 2019 EX-99.(H)(1)

HIGHLAND INCOME FUND (a Massachusetts Business Trust) 5,400,000 Shares of 5.375% Series A Cumulative Preferred Shares UNDERWRITING AGREEMENT

Underwriting Agreement Exhibit (h) EXECUTION VERSION HIGHLAND INCOME FUND (a Massachusetts Business Trust) 5,400,000 Shares of 5.

July 31, 2019 EX-99.(A)(2)

HIGHLAND INCOME FUND STATEMENT OF PREFERENCES 5.375% SERIES A CUMULATIVE PREFERRED SHARES

Statement of Preferences Exhibit (a)(2) EXECUTION VERSION HIGHLAND INCOME FUND STATEMENT OF PREFERENCES OF 5.

July 31, 2019 EX-99.(H)(2)

Morgan Stanley & Co. LLC MASTER AGREEMENT AMONG UNDERWRITERS REGISTERED SEC OFFERINGS (INCLUDING MULTIPLE SYNDICATE OFFERINGS) EXEMPT OFFERINGS (OTHER THAN OFFERINGS OF MUNICIPAL SECURITIES)

Form of Master Agreement Among Underwriters Exhibit (h)(2) Morgan Stanley & Co. LLC MASTER AGREEMENT AMONG UNDERWRITERS REGISTERED SEC OFFERINGS (INCLUDING MULTIPLE SYNDICATE OFFERINGS) AND EXEMPT OFFERINGS (OTHER THAN OFFERINGS OF MUNICIPAL SECURITIES) January 1, 2019 This Master Agreement Among Underwriters (this “Master AAU”), dated as of January 1, 2019, is by and between Morgan Stanley & Co.

July 31, 2019 POS EX

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND POS EX - - HIGHLAND INCOME FUND

POS EX 1 d783455dposex.htm HIGHLAND INCOME FUND As filed with the Securities and Exchange Commission on July 31, 2019 Securities Act of 1933 Registration No. 333-219103 Investment Company Act of 1940 Registration No. 811-23268 SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM N-2 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Post-Effective Amendment No. 1 and REGISTRATION ST

July 31, 2019 EX-99.(H)(3)

Morgan Stanley & Co. LLC MASTER SELECTED DEALERS AGREEMENT REGISTERED SEC OFFERINGS EXEMPT OFFERINGS (OTHER THAN OFFERINGS OF MUNICIPAL SECURITIES)

Form of Master Selected Dealers Agreement Exhibit (h)(3) Morgan Stanley & Co. LLC MASTER SELECTED DEALERS AGREEMENT REGISTERED SEC OFFERINGS AND EXEMPT OFFERINGS (OTHER THAN OFFERINGS OF MUNICIPAL SECURITIES) March 1, 2019 This Master Selected Dealers Agreement (this “Master SDA”), dated as of March 1, 2019, is by and between Morgan Stanley & Co. LLC (including its successors and assigns) (“we,” “

July 31, 2019 EX-99.(L)

K&L Gates LLP

Opinion and consent of Legal Counsel K&L Gates LLP State Street Financial Center One Lincoln Street Boston, MA 02111-2950 T 617.

July 31, 2019 EX-99.(K)(5)

ADDENDUM TO TRANSFER AGENCY AND REGISTRAR SERVICES AGREEMENT

Addendum to Transfer Agency and Registrar Services Agreement ADDENDUM TO TRANSFER AGENCY AND REGISTRAR SERVICES AGREEMENT This Addendum (this “Addendum”), is made as of July 29, 2019, by and between Highland Income Fund (formerly, Highland Floating Rate Opportunities Fund), a Massachusetts business trust (the “Company”) and American Stock Transfer & Trust Company, LLC, a New York limited liability trust company (“AST”).

July 1, 2019 CORRESP

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND CORRESP - -

Correspondence R. Charles Miller 202-778-9372 [email protected] July 1, 2019 VIA EDGAR Jay Williamson Securities and Exchange Commission 100 F Street, NE Washington, DC 20549 Re: Highland Income Fund File Nos. 333-219103; 811-23268 Dear Mr. Williamson: On behalf of the Highland Income Fund (the “Fund”), we hereby transmit for filing with the U.S. Securities and Exchange Commission (the “S

May 30, 2019 NPORT-EX

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND NPORT-EX - - PART F

HTML INVESTMENT PORTFOLIO (unaudited) As of March 31, 2019 Highland Floating Rate Opportunities Fund‡ Principal Amount ($) Value ($) U.

May 13, 2019 DEFA14A

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND DEFA14A FORM DEFA14A

Form DEFA14A SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy Statement ☒ Definitive Additional Materials ☐ Soliciting Material Pursuant to Sec.

May 8, 2019 DEF 14A

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND DEF 14A FORM DEF 14A

Form DEF 14A SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Soliciting Material Pursuant to Sec.

May 8, 2019 CORRESP

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND CORRESP - -

Form CORRESP May 8, 2019 VIA EDGAR Jay Williamson Securities and Exchange Commission 100 F Street, NE Washington, DC 20549 Re: Highland Floating Rate Opportunities Fund File Nos.

April 23, 2019 PRE 14A

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND FORM PRE 14A

PRE 14A 1 d717164dpre14a.htm FORM PRE 14A SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy Statement ☐ Definitive

November 28, 2018 EX-99.CERT

Certification Pursuant to Rule 30a-2(a) under the 1940 Act and Section 302 of the Sarbanes-Oxley Act

Certifications EX99.CERT Certification Pursuant to Rule 30a-2(a) under the 1940 Act and Section 302 of the Sarbanes-Oxley Act I, Frank Waterhouse, certify that: 1. I have reviewed this report on Form N-Q of Highland Floating Rate Opportunities Fund; 2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the

November 28, 2018 N-Q

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND FORM N-Q (Quarterly Schedule of Portfolio Holdings)

Form N-Q UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM N-Q QUARTERLY SCHEDULE OF PORTFOLIO HOLDINGS OF REGISTERED MANAGEMENT INVESTMENT COMPANY Investment Company Act file number: 811-23268 Highland Floating Rate Opportunities Fund (Exact name of registrant as specified in charter) 200 Crescent Court Suite 700 Dallas, Texas 75201 (Address of principal executive offic

September 13, 2018 NT-NCEN

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND FORM NT-NCEN

NT-NCEN 1 d621452dntncen.htm FORM NT-NCEN SEC FILE NUMBER 811-23268 CUSIP NUMBER 43010E404 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☒ Form N-CEN ☐ Form N-CSR For Period Ended: June 30, 2018 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F

September 10, 2018 NT-NCSR

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND FORM NT-NCSR

NT-NCSR 1 d571528dntncsr.htm FORM NT-NCSR UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SEC FILE NUMBER 811-23268 CUSIP NUMBER 43010E404 FORM 12b-25 NOTIFICATION OF LATE FILING (Check One) ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☒ Form N-CSR For Period Ended: June 30, 2018 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐

June 13, 2018 8-K

Other Events

FORM 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 12, 2018 HIGHLAND FLOATING RATE OPPORTUNITIES FUND (Exact name of Registrant as Specified in Its Charter) Massachusetts 811-23268 45-6245636 (State or Other Jurisdiction

May 25, 2018 EX-99.CERT

Certification Pursuant to Rule 30a-2(a) under the 1940 Act and Section 302 of the Sarbanes-Oxley Act

Certifications EX99.CERT Certification Pursuant to Rule 30a-2(a) under the 1940 Act and Section 302 of the Sarbanes-Oxley Act I, Frank Waterhouse, certify that: 1. I have reviewed this report on Form N-Q Highland Floating Rate Opportunities Fund; 2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the sta

May 25, 2018 N-Q

Highland Floating Rate Opportunities Fund - FORM N-Q

N-Q 1 d589076dnq.htm FORM N-Q UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM N-Q QUARTERLY SCHEDULE OF PORTFOLIO HOLDINGS OF REGISTERED MANAGEMENT INVESTMENT COMPANY Investment Company Act file number: 811-23268 Highland Floating Rate Opportunities Fund (Exact name of registrant as specified in charter) 200 Crescent Court Suite 700 Dallas, Texas 75201 (Address of prin

May 25, 2018 DEF 14A

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND FORM DEF 14A

Form DEF 14A SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to Sec.

February 2, 2018 8-K

Other Events

8-K 1 d463349d8k.htm FORM 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 2, 2018 HIGHLAND FLOATING RATE OPPORTUNITIES FUND (Exact name of Registrant as Specified in Its Charter) Massachusetts 811-23268 45-6245636 (Sta

November 28, 2017 N-Q

Highland Floating Rate Opportunities Fund - FORM N-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM N-Q QUARTERLY SCHEDULE OF PORTFOLIO HOLDINGS OF REGISTERED MANAGEMENT INVESTMENT COMPANY Investment Company Act file number: 811-23268 Highland Floating Rate Opportunities Fund (Exact name of registrant as specified in charter) 200 Crescent Court Suite 700 Dallas, Texas 75201 (Address of principal executive offices)(Zip c

November 28, 2017 EX-99.CERT

Certification Pursuant to Rule 30a-2(a) under the 1940 Act and Section 302 of the Sarbanes-Oxley Act

Certifications EX-99.CERT Certification Pursuant to Rule 30a-2(a) under the 1940 Act and Section 302 of the Sarbanes-Oxley Act I, Brad Ross, certify that: 1. I have reviewed this report on Form N-Q of Highland Floating Rate Opportunities Fund; 2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statem

November 3, 2017 8-A12B

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 Highland Floating Rate Opportunities Fund (Exact name of re

8-A12B 1 d486690d8a12b.htm FORM 8-A12B SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 Highland Floating Rate Opportunities Fund (Exact name of registrant as specified in its charter) Massachusetts 45-6245636 (Jurisdiction of Incorporation or Organization)

October 12, 2017 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☑ Filed by a Party other than the Registrant ☐ Check the appropriate box: [ ] Preliminary Proxy Statement [ ] Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) [X] Definitive Proxy Statement [ ] Definitive Additional Materials [ ] Soliciting Material Pursuant to §240.

October 11, 2017 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

Definitive Proxy Statement UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☑ Filed by a Party other than the Registrant ☐ Check the appropriate box: [ ] Preliminary Proxy Statement [ ] Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) [X] Definitive Proxy Statement [ ] Definitive Additional Materials [ ] Soliciting Material Pursuant to §240.

October 5, 2017 CORRESP

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ROPES & GRAY LLP PRUDENTIAL TOWER 800 BOYLSTON STREET BOSTON, MA 02199-3600 WWW.ROPESGRAY.COM October 5, 2017 Jessica L. Reece T +1 617 235 4636 [email protected] BY EDGAR United States Securities & Exchange Commission Division of Investment Management 100 F Street, NE Washington, DC 20549 Attention: Angela Mokodean Re: Highland Floating Rate Opportunities Fund Proxy Statement on Schedul

September 25, 2017 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ___)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

August 30, 2017 CORRESP

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND CORRESP

SEC Response Letter August 30, 2017 Angela Mokodean Securities and Exchange Commission Division of Investment Management 100 F Street, NE Washington, D.

August 25, 2017 EX-99.(N)

HIGHLAND FUNDS I HIGHLAND FUNDS II HIGHLAND FLOATING RATE OPPORTUNITIES FUND II HIGHLAND GLOBAL ALLOCATION FUND II AMENDED AND RESTATED RULE 18f-3 MULTI-CLASS PLAN

Exhibit (n) HIGHLAND FUNDS I HIGHLAND FUNDS II HIGHLAND FLOATING RATE OPPORTUNITIES FUND II HIGHLAND GLOBAL ALLOCATION FUND II AMENDED AND RESTATED RULE 18f-3 MULTI-CLASS PLAN This Amended and Restated Rule 18f-3 Multi-Class Plan (the ?Multi-Class Plan?) is adopted pursuant to Rule 18f-3 under the Investment Company Act of 1940, as amended (the ?Act?), to provide for the issuance and distribution

August 25, 2017 CORRESP

HFRO / HIGHLAND FLOATING RATE OPPORTUNITIES FUND CORRESP

Acceleration Request Letter HIGHLAND FLOATING RATE OPPORTUNITIES FUND II 200 Crescent Court, Suite 700 Dallas, Texas 75201 August 25, 2017 United States Securities and Exchange Commission 100 F Street N.

August 25, 2017 EX-99.(P)(2)

CODE OF ETHICS POLICY Purpose and Scope

Exhibit (p)(2) CODE OF ETHICS POLICY Purpose and Scope The purpose of the Code of Ethics Policy (?the Policy?) is to implement a policy of strict compliance with the highest standards of ethical business conduct and the provisions of applicable federal securities laws, including rules and regulations promulgated by the SEC.

August 25, 2017 CORRESP

August 25, 2017

ROPES & GRAY LLP ONE INTERNATIONAL PLACE BOSTON, MA 02110-2624 617-951-7000 F 617-951-7050 BOSTON NEW YORK SAN FRANCISCO WASHINGTON, DC August 25, 2017 Securities and Exchange Commission 100 F Street, N.

August 25, 2017 CORRESP

* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *

ROPES & GRAY LLP 800 Boylston Street Boston, MA 02199-3600 [email protected] August 25, 2017 Angela Mokodean Securities and Exchange Commission Division of Investment Management 100 F Street, NE Washington, D.C. 20549 Phone: (202) 551-5490 Re: Highland Floating Rate Opportunities Fund II Pre-Effective Amendment No. 1 to the Registration Statement on Form N-1A File Nos. 333-219103 and 811

August 25, 2017 EX-99.(E)(1)

DISTRIBUTION AGREEMENT

Exhibit (e)(1) DISTRIBUTION AGREEMENT This Distribution Agreement (?Agreement?) is made by and between the investment companies of the Highland Family of Funds, identified on Schedule A (each a ?Fund? and collectively, the ?Funds?) and Highland Capital Fund Distributors, (the ?Distributor?), and is effective as of the date accepted and agreed to by the Distributor below .

August 25, 2017 EX-99.(I)

- 2 -

Exhibit (i) ROPES & GRAY LLP PRUDENTIAL TOWER 800 BOYLSTON STREET BOSTON, MA 02199-3600 WWW.

August 25, 2017 EX-99.(E)(2)

SELLING AND/OR SERVICES AGREEMENT HIGHLAND FAMILY OF FUNDS

Exhibit (e)(2) SELLING AND/OR SERVICES AGREEMENT FOR HIGHLAND FAMILY OF FUNDS This Selling and/or Services Agreement (?Agreement?) is made by and between [NAME OF INTERMEDIARY] (?Intermediary?) and Highland Capital Funds Distributor, Inc.

August 25, 2017 EX-99.(H)(3)

TRANSFER AGENCY AND SERVICE AGREEMENT EACH OF THE ENTITIES, INDIVIDUALLY AND NOT JOINTLY, AS LISTED ON SCHEDULE A BOSTON FINANCIAL DATA SERVICES, INC.

Exhibit (h)(3) EXECUTION COPY TRANSFER AGENCY AND SERVICE AGREEMENT BETWEEN EACH OF THE ENTITIES, INDIVIDUALLY AND NOT JOINTLY, AS LISTED ON SCHEDULE A AND BOSTON FINANCIAL DATA SERVICES, INC.

August 25, 2017 EX-99.(J)(2)

Consent of Independent Registered Public Accounting Firm

Exhibit (j)(2) Consent of Independent Registered Public Accounting Firm The Board of Trustees and Shareholders Highland Floating Rate Opportunities Fund II: We consent to the references to our firm under the heading ?INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM? in the prospectus and in the statement of additional information. /s/ KPMG LLP Boston, Massachusetts August 25, 2017

August 25, 2017 EX-99.(H)(4)

SECURITIES LENDING AND SERVICES AGREEMENT HIGHLAND FUNDS I (F/K/A PYXIS FUNDS I) ON BEHALF OF EACH OF ITS SERIES LISTED ON SCHEDULE C STATE STREET BANK AND TRUST COMPANY

Exhibit (h)(4) SECURITIES LENDING AND SERVICES AGREEMENT BETWEEN HIGHLAND FUNDS I (F/K/A PYXIS FUNDS I) ON BEHALF OF EACH OF ITS SERIES LISTED ON SCHEDULE C AND STATE STREET BANK AND TRUST COMPANY Exhibit (h)(4) SECURITIES LENDING AND SERVICES AGREEMENT Agreement (the ?Agreement?) dated the 4th day of March 2013 between Highland Funds I (f/k/a Pyxis Funds I) (the ?Trust?), on behalf of each of its

August 25, 2017 EX-99.(G)(1)

MASTER CUSTODIAN

Exhibit (g)(1) Execution Version MASTER CUSTODIAN AGREEMENT This Agreement is made as of October 1, 2012 by and among each management investment company identified on Appendix A and Appendix B hereto (each such investment company and each management investment company made subject to this Agreement in accordance with Section 19.

August 25, 2017 EX-99.(E)(1)(II)

Schedule A To the Distribution Agreement List of Funds Dated as of August , 2017

Exhibit (e)(1)(ii) Schedule A To the Distribution Agreement List of Funds Dated as of August , 2017 All Share Classes of the Following Funds: Highland Funds I: Highland Long/Short Equity Fund Highland Long/Short Healthcare Fund Highland Floating Rate Opportunities Fund Highland/iBoxx Senior Loan ETF Highland Merger Arbitrage Fund Highland Opportunistic Credit Fund Highland Funds II: Highland Small

August 25, 2017 EX-99.(B)

BYLAWS OF HIGHLAND FLOATING RATE OPPORTUNITIES FUND II (Dated as of June 28, 2017) ARTICLE 1 Agreement and Declaration of Trust

Exhibit (b) BYLAWS OF HIGHLAND FLOATING RATE OPPORTUNITIES FUND II (Dated as of June 28, 2017) ARTICLE 1 Agreement and Declaration of Trust 1.

August 25, 2017 EX-99.(E)(1)(I)

Schedule A To the Distribution Agreement List of Funds Dated as of August 5, 2016

Exhibit (e)(1)(i) Schedule A To the Distribution Agreement List of Funds Dated as of August 5, 2016 All Share Classes of the Following Funds: Highland Funds I: Highland Long/Short Equity Fund Highland Long/Short Healthcare Fund Highland Floating Rate Opportunities Fund Highland/iBoxx Senior Loan ETF Highland Opportunistic Credit Fund Highland Merger Arbitrage Fund Highland Funds II: Highland Small

August 25, 2017 EX-99.(Q)

HIGHLAND FLOATING RATE OPPORTUNITIES FUND II HIGHLAND GLOBAL ALLOCATION FUND II POWER OF ATTORNEY

Exhibit (q) HIGHLAND FLOATING RATE OPPORTUNITIES FUND II HIGHLAND GLOBAL ALLOCATION FUND II POWER OF ATTORNEY Highland Floating Rate Opportunities Fund II and Highland Global Allocation Fund II (collectively, the ?Trusts?) and the undersigned Trustee constitutes and appoints each of J.

August 25, 2017 EX-99.(D)

FORM OF INVESTMENT ADVISORY AGREEMENT

Exhibit (d) FORM OF INVESTMENT ADVISORY AGREEMENT AGREEMENT made as of [ ], by and between Highland Capital Management Fund Advisors, L.

August 25, 2017 EX-99.(H)(1)(I)

Highland Floating Rate Opportunities Funds II 200 Crescent Court, Suite 700 Dallas, Texas 75201 August , 2017

Exhibit (h)(1)(i) Highland Floating Rate Opportunities Funds II 200 Crescent Court, Suite 700 Dallas, Texas 75201 August , 2017 Highland Capital Management Fund Advisors, L.

August 25, 2017 EX-99.(J)(1)

CONSENT OF LEGAL COUNSEL

Exhibit (j)(1) CONSENT OF LEGAL COUNSEL We hereby consent to the use of our name and the references to our firm under the caption ?Legal Counsel? included in or made a part of Pre-Effective Amendment No.

August 25, 2017 EX-99.(G)(1)(I)

APPENDIX A MASTER CUSTODIAN AGREEMENT

Exhibit (g)(1)(i) August , 2017 State Street Bank and Trust Company Channel Center, Mailstop CCB0502 1 Iron Street Boston, MA 02210 Attention: Brett Fernquist, Managing Director Re: Highland Floating Rate Opportunities Fund II and Highland Global Allocation Fund II (the ?Funds?) Ladies and Gentlemen: Please be advised that the undersigned Funds have been incorporated and registered as management investment companies under the Investment Company Act of 1940, as amended.

August 25, 2017 EX-99.(M)

HIGHLAND FUNDS I HIGHLAND FUNDS II HIGHLAND FLOATING RATE OPPORTUNITIES FUND II HIGHLAND GLOBAL ALLOCATION FUND II CLASS A SHARES, CLASS C SHARES AND CLASS T SHARES AMENDED AND RESTATED RULE 12b-1 DISTRIBUTION PLAN

Exhibit (m) HIGHLAND FUNDS I HIGHLAND FUNDS II HIGHLAND FLOATING RATE OPPORTUNITIES FUND II HIGHLAND GLOBAL ALLOCATION FUND II CLASS A SHARES, CLASS C SHARES AND CLASS T SHARES AMENDED AND RESTATED RULE 12b-1 DISTRIBUTION PLAN Highland Funds I, a Delaware statutory trust, Highland Funds II, Highland Floating Rate Opportunities Fund II, and Highland Global Allocation Fund II, each a Massachusetts s

August 25, 2017 N-1A/A

As filed with the Securities and Exchange Commission on August 25, 2017

As filed with the Securities and Exchange Commission on August 25, 2017 Securities Act of 1933 Registration No.

August 25, 2017 EX-99.(P)(3)

HCFD

Exhibit (p)(3) HCFD The Code of Ethics All registered representatives and associated persons must: ? Act with integrity, competence, diligence, respect and in an ethical manner with the public, customers, prospective customers, employers, employees, colleagues in the investment profession, and other participants in the global capital markets.

August 25, 2017 EX-99.(P)(1)

CODE OF ETHICS Highland Funds I, Highland Funds II, NexPoint Credit Strategies Fund, NexPoint Real Estate Strategies Fund, NexPoint Opportunistic Credit Fund, NexPoint Capital, Inc., Highland Floating Rate Opportunities Fund II and Highland Global Al

Exhibit (p)(1) CODE OF ETHICS of Highland Funds I, Highland Funds II, NexPoint Credit Strategies Fund, NexPoint Real Estate Strategies Fund, NexPoint Opportunistic Credit Fund, NexPoint Capital, Inc.

August 25, 2017 EX-99.(H)(1)

ADMINISTRATION SERVICES AGREEMENT

Exhibit (h)(1) ADMINISTRATION SERVICES AGREEMENT THIS AGREEMENT is made as of December 4, 2006 by and between HIGHLAND CAPITAL MANAGEMENT, L.

August 25, 2017 EX-99.(A)

HIGHLAND FLOATING RATE OPPORTUNITIES FUND II AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST

Exhibit (a) HIGHLAND FLOATING RATE OPPORTUNITIES FUND II AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST THIS AMENDED AND RESTATED AGREEMENT AND DECLARATION OF TRUST made on this 17th day of August, 2017 by the Trustees hereunder and by the holders of shares of beneficial interest issued hereunder and to be issued hereunder as hereinafter provided, amending and restating the Agreement and

August 25, 2017 EX-99.(H)(2)(I)

MASTER SUB-ADMINISTRATION AGREEMENT SCHEDULE A Listing of Trusts and Funds

Exhibit (h)(2)(i) , 2017 State Street Bank and Trust Company Channel Center, Mailstop CCB0502 1 Iron Street Boston, MA 02210 Attention: Brett Fernquist, Managing Director Re: HIGHLAND FLOATING RATE OPPORTUNITIES FUND II (the ?Trust?) Ladies and Gentlemen: Please be advised that the undersigned Trust has established a new series of shares to be known as HIGHLAND FLOATING RATE OPPORTUNITIES FUND II.

August 25, 2017 EX-99.(H)(3)(I)

AMENDMENT Transfer Agency and Service Agreement Highland Funds Each of the Entities, Individually and not Jointly, as listed on Schedule A Boston Financial Data Services, Inc.

Exhibit (h)(3)(i) AMENDMENT to Transfer Agency and Service Agreement between Highland Funds Each of the Entities, Individually and not Jointly, as listed on Schedule A and Boston Financial Data Services, Inc.

August 25, 2017 EX-99.(H)(2)

MASTER SUB-ADMINISTRATION AGREEMENT

Exhibit (h)(2) Execution Copy MASTER SUB-ADMINISTRATION AGREEMENT This Master Sub-Administration Agreement (?Agreement?) dated and effective as of January 7, 2013, is by and between State Street Bank and Trust Company, a Massachusetts trust company (the ?Sub-Administrator? ), and Pyxis Capital, L.

August 11, 2017 CORRESP

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SEC Response Letter ROPES & GRAY LLP 800 Boylston Street Boston, MA 02199-3600 Jessica.

August 11, 2017 N-1A/A

As filed with the Securities and Exchange Commission on August 11, 2017

Table of Contents As filed with the Securities and Exchange Commission on August 11, 2017 Securities Act of 1933 Registration No.

August 11, 2017 CORRESP

ROPES & GRAY LLP

ROPES & GRAY LLP 800 Boylston Street Boston, MA 02199-3600 [email protected] August 11, 2017 Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Highland Floating Rate Opportunities Fund II (File Nos. 333-219103; 811-23268) Ladies and Gentlemen: We are filing today through EDGAR, Pre-Effective Amendment No.1 to the Initial Registration Statement on Form N-1A

June 30, 2017 EX-99.(A)(1)

HIGHLAND FLOATING RATE OPPORTUNITIES FUND II AGREEMENT AND DECLARATION OF TRUST

Exhibit (a)(1) HIGHLAND FLOATING RATE OPPORTUNITIES FUND II AGREEMENT AND DECLARATION OF TRUST THIS AGREEMENT AND DECLARATION OF TRUST made at Boston, Massachusetts, on this 28th day of June, 2017 by the Trustees hereunder and by the holders of shares of beneficial interest issued hereunder and to be issued hereunder as hereinafter provided: WITNESSETH that: WHEREAS, this Trust has been formed to

June 30, 2017 CORRESP

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SEC Letter ROPES & GRAY LLP PRUDENTIAL TOWER 800 BOYLSTON STREET BOSTON, MA 02199-3600 WWW.

June 30, 2017 N-1A

As filed with the Securities and Exchange Commission on June 30, 2017

Table of Contents As filed with the Securities and Exchange Commission on June 30, 2017 Securities Act of 1933 Registration No.

June 30, 2017 N-8A

U.S. SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM N-8A NOTIFICATION OF REGISTRATION FILED PURSUANT TO SECTION 8(a) OF THE INVESTMENT COMPANY ACT OF 1940

U.S. SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM N-8A NOTIFICATION OF REGISTRATION FILED PURSUANT TO SECTION 8(a) OF THE INVESTMENT COMPANY ACT OF 1940 The undersigned investment company hereby notifies the Securities and Exchange Commission that it registers under and pursuant to the provisions of Section 8(a) of the Investment Company Act of 1940 and in connection with such no

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