<Page> EXHIBIT 4.19 FOURTH SUPPLEMENTAL INDENTURE SUPPLEMENTAL INDENTURE (this "Supplemental Indenture"), dated as of September 28, 1998, among Von Hoffmann Press, Inc., a Missouri corporation (the "Company"), Von Hoffmann Corporation, a Delaware corporation, and Marine Midland Bank, as trustee under the indenture referred to below (the "Trustee"). Capitalized terms used herein and not defined herein shall have the meaning ascribed to them in the Indenture (as defined below). W I T N E S S E T H WHEREAS, the Company has heretofore executed and delivered to the Trustee an indenture (the "Indenture"), dated as of May 22, 1997, providing for the issuance of an aggregate principal amount of $100,000,000 of 10 3/8% Senior Subordinated Notes due 2007 (the "Notes"); WHEREAS, Von Hoffmann Corporation, a Missouri corporation ("VHC Missouri"), is a Guarantor under the Indenture; WHEREAS, on September 28, 1998, VHC Missouri merged with and into Von Hoffmann Corporation, a Delaware corporation and, prior to such merger, a wholly-owned subsidiary of VHC Missouri ("VHC Delaware"), with VHC Delaware as the surviving corporation of such merger; WHEREAS, Article 11 of the Indenture provides that under certain circumstances a successor to a Guarantor must execute and deliver to the Trustee a supplemental indenture pursuant to which such successor shall unconditionally guarantee all of the Company's Obligations under the Notes pursuant to a Notes Guarantee on the terms and conditions set forth herein; and WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee is authorized to execute and deliver this Supplemental Indenture. NOW THEREFORE, in consideration of the foregoing and for other good and valuable consideration, the receipt of which is hereby acknowledged, the Company, VHC Delaware and the Trustee mutually covenant and agree for the equal and ratable benefit of the Holders of the Notes as follows: <Page> 1. CAPITALIZED TERMS. Capitalized terms used herein without definition shall have the meanings assigned to them in the Indenture. 2. AGREEMENT TO NOTES GUARANTEE. VHC Delaware hereby agrees to assume all of the Obligations of VHC Missouri as a Guarantor and, as such, agrees, jointly and severally with all other Guarantors, to guarantee the Company's Obligations under the Notes and the Indenture on the terms and subject to the conditions set forth in Article 11 of the Indenture and to be bound by all other applicable provisions of the Indenture. 3. NO RECOURSE AGAINST OTHERS. No past, present or future director, officer, employee, incorporator, shareholder or agent of any Guarantor, as such, shall have any liability for any obligations of the Company or any Guarantor under the Notes, any Notes Guarantees, the Indenture or this Supplemental Indenture or for any claim based on, in respect of, or by reason of, such obligations or their creation. Each Holder by accepting a Note waives and releases all such liability. The waiver and release are part of the consideration for issuance of the Notes. 4. NEW YORK LAW TO GOVERN. THE INTERNAL LAW OF THE STATE OF NEW YORK SHALL GOVERN AND BE USED TO CONSTRUE THIS SUPPLEMENTAL INDENTURE. 5. COUNTERPARTS. The parties may sign any number of copies of this Supplemental Indenture. Each signed copy shall be an original, but all of them together represent the same agreement. 6. EFFECT OF HEADINGS. The Section headings herein are for convenience only and shall not affect the construction hereof. 7. THE TRUSTEE. The Trustee shall not be responsible in any manner whatsoever for or in respect of the validity or sufficiency of this Supplemental Indenture or for or in respect of the correctness of the recitals of fact contained herein, all of which recitals are made solely by the Company and VHC Delaware. 2 <Page> IN WITNESS WHEREOF, the parties hereto have caused this Supplemental Indenture to be duly executed and attested, all as of the date first above written. Dated: September 28, 1998 VON HOFFMANN PRESS, INC. By: /s/ Robert A. Uhlenhop ---------------------------------------- Robert A. Uhlenhop President Dated: September 28, 1998 VON HOFFMANN CORPORATION By: /s/ Robert A. Uhlenhop ---------------------------------------- Robert A. Uhlenhop President Dated: September 28, 1998 MARINE MIDLAND BANK, as Trustee By: /s/ Marcia Markowski ---------------------------------------- Name: Marcia Markowski Title: Assistant Vice President 3