Chapman and Cutler LLP 111 West Monroe Street Chicago, Illinois 60603 April 8, 2016 Mr. Edward Bartz Division of Investment Management Securities and Exchange Commission 100 F Street, N.E. Washington, DC 20549 Re: Guggenheim Defined Portfolios, Series 1444 Convertible & Income Portfolio of Funds, Series 23 File Nos. 333-209803 and 811-03763 -------------------------------------------------------------------------------- Dear Mr. Bartz: This letter is in response to your comments given during a telephone conversation with our office regarding the registration statement on Form S-6 for Guggenheim Defined Portfolios, Series 1444, filed on February 29, 2016, with the Securities and Exchange Commission (the "Commission"). The registration statement proposes to offer the Convertible & Income Portfolio of Funds, Series 23 (the "Trust"). PROSPECTUS INVESTMENT SUMMARY -- PRINCIPAL RISKS 1. The duration example in the sixth bullet uses a duration of three years. Please confirm that the average weighted duration of the underlying securities is approximately three years or less. If not, please revise this example to reflect the average weighted duration of the underlying securities. Response: We confirm that the average weighted duration of the underlying securities is approximately three years or less and, therefore, the example does not need to be revised. We appreciate your prompt attention to this registration statement. If you have any questions or comments or would like to discuss our responses to your questions please feel free to contact the undersigned at (312) 845-3484. Very truly yours, CHAPMAN AND CUTLER LLP By /s/ Morrison C. Warren ------------------------- Morrison C. Warren