Exhibit 5 Jenkens & Gilchrist Parker Chapin LLP AUSTIN, TEXAS (512) 499-3800 THE CHRYSLER BUILDING CHICAGO, ILLINOIS 405 LEXINGTON AVENUE (312) 425-3900 NEW YORK, NEW YORK 10174 DALLAS, TEXAS (214) 855-4500 (212) 704-6000 HOUSTON, TEXAS FACSIMILE (212) 704-6288 (713) 951-3300 LOS ANGELES, CALIFORNIA www.jenkens.com (310) 820-8800 SAN ANTONIO, TEXAS (210) 246-5000 WASHINGTON, D.C. (202) 326-1500 October 7, 2002 SmartServ Online, Inc. Metro Center One Station Place Stamford, CT 06902 Gentlemen: We have acted as counsel to SmartServ Online, Inc., a Delaware corporation (the "Company"), in connection with the Company's filing of a Registration Statement on Form S-3 (the "Registration Statement") with the Securities and Exchange Commission (the "Commission") under the Securities Act of 1933, as amended (the "Act"), relating to the resale of an aggregate of 45,064 shares (the "Non-Callable Warrant Shares") of Common Stock, par value $.01 per share (the "Common Stock"), of the Company, issuable upon exercise of non-callable warrants (the "Non-Callable Warrants") issued by the Company to Bonanza Master Fund, Ltd. ("Bonanza") and Vertical Ventures Investments LLC ("Vertical"; Bonanza and Vertical are collectively referred to herein as the "Investors"), and 84,926 shares of Common Stock issuable upon the triggering of certain anti-dilution provisions contained in the Non-Callable Warrants (the "Anti-Dilution Shares"; the Non-Callable Warrant Shares and the Anti-Dilution Shares are collectively referred to herein as the "Warrant Shares"). In connection with the foregoing, we have examined originals or copies, satisfactory to us, of: (i) the Securities Purchase Agreement, dated May 20, 2002, as amended on June 5, 2002 (the "Purchase Agreement"), (ii) the Non-Callable Warrants, (iii) the Company's Certificate of Incorporation, as amended, (iv) the Company's By-laws, and (vi) resolutions of the Company's board of directors authorizing the Company to enter into, and consummate, the transactions contemplated by the Purchase Agreement, including the issuance of the Non-Callable Warrants. We have also reviewed such other matters of law as we have deemed relevant and necessary as a basis for the opinion hereinafter expressed. In such examination, we have assumed the genuineness of all signatures, the authenticity of all documents submitted to us as originals and the conformity with the original documents of all documents submitted to us as copies or facsimiles. As to any facts material to such opinion, we have, to the extent that relevant facts were not independently established by us, relied on certificates of public officials and certificates of officers or other representatives of the Company. Jenkens & Gilchrist Parker Chapin LLP SmartServ Online, Inc. October 7, 2002 Page 2 Based upon and subject to the foregoing, we are of the opinion that the Warrant Shares, upon issuance and payment by the Investors to the Company in accordance with the terms of the Non-Callable Warrants, will be validly issued, fully paid and non-assessable. We hereby consent to the filing of this opinion as an exhibit to the Registration Statement and to the reference made to us under the caption "Legal Matters" in the prospectus constituting part of the Registration Statement. In giving this consent, we do not thereby admit that we are within the category of persons whose consent is required under Section 7 of the Act, the rules and regulations of the Commission promulgated under Section 7 of the Act or Item 509 of Regulation S-B promulgated under the Act. Very truly yours, /s/ Jenkens & Gilchrist Parker Chapin LLP JENKENS & GILCHRIST PARKER CHAPIN LLP