Document:

<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<Page>

                                                                    EXHIBIT 4.20

                          FIFTH SUPPLEMENTAL INDENTURE

     SUPPLEMENTAL INDENTURE (this "Supplemental Indenture"), dated as of
September 29, 1998, among Von Hoffmann Press, Inc., a Delaware corporation, Von
Hoffmann Corporation, a Delaware corporation, Mid-Missouri Graphics, Inc., a
Missouri corporation, One Thousand Realty & Investment Company, a Missouri
corporation, Bawden Printing, Inc., an Iowa corporation, H&S Graphics, Inc., a
Delaware corporation, Preface, Inc., a Delaware corporation, Custom Printing
Company, a Missouri 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, Von Hoffmann Press, Inc., a Missouri corporation ("VHP Missouri")
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, each of Von Hoffmann Corporation, a Delaware corporation,
Mid-Missouri Graphics, Inc., a Missouri corporation, One Thousand Realty &
Investment Company, a Missouri corporation, Bawden Printing, Inc., an Iowa
corporation, H&S Graphics, Inc., a Delaware corporation, Preface, Inc., a
Delaware corporation, and Custom Printing Company, a Missouri corporation, is a
Guarantor under the Indenture;

     WHEREAS, on September 29, 1998, VHP Missouri merged with and into Von
Hoffmann Press, Inc., a Delaware corporation and, prior to such merger, a
wholly-owned subsidiary of VHP Missouri ("VHP Delaware"), with VHP Delaware as
the surviving corporation of such merger;

     WHEREAS, Article 5 of the Indenture provides that under certain
circumstances a successor to VHP Missouri must execute and deliver to the
Trustee a supplemental indenture pursuant to which such successor shall
unconditionally assume all of VHP Missouri's Obligations under the Notes and the
Indenture; and

<Page>

     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, VHP
Delaware, the Guarantors and the Trustee mutually covenant and agree for the
equal and ratable benefit of the Holders of the Notes as follows:

     1.   CAPITALIZED TERMS. Capitalized terms used herein without definition
shall have the meanings assigned to them in the Indenture.

     2.   AGREEMENT OF VHP DELAWARE. VHP Delaware hereby agrees to assume all of
the Obligations of VHP Missouri under the Notes and the Indenture and to be
bound by all other applicable provisions of the Indenture.

     3.   AGREEMENT TO NOTES GUARANTEES. Each Guarantor hereby confirms that its
respective Notes Guarantee shall apply to VHP Delaware's Obligations under the
Indenture and the Notes.

     4.   NO RECOURSE AGAINST OTHERS. No past, present or future director,
officer, employee, incorporator, shareholder or agent of VHP Delaware or of any
Guarantor, as such, shall have any liability for any obligations of VHP Delaware
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.

     5.   NEW YORK LAW TO GOVERN. THE INTERNAL LAW OF THE STATE OF NEW YORK
SHALL GOVERN AND BE USED TO CONSTRUE THIS SUPPLEMENTAL INDENTURE.

     6.   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.

     7.   EFFECT OF HEADINGS. The Section headings herein are for convenience
only and shall not affect the construction hereof.

                                        2
<Page>

     8.   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 VHP Delaware.

     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 29, 1998            VON HOFFMANN PRESS, INC.

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        President

Dated: September 29, 1998            VON HOFFMANN CORPORATION

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        President

Dated: September 29, 1998            MID-MISSOURI GRAPHICS, INC.

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        President

Dated: September 29, 1998            ONE THOUSAND REALTY &
                                     INVESTMENT COMPANY

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        President

                                        3
<Page>

Dated: September 29, 1998            BAWDEN PRINTING, INC

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        Chief Executive Officer

Dated: September 29,  1998           H&S GRAPHICS, INC.

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        Chief Executive Officer

Dated: September 29,  1998           PREFACE, INC.

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        Chief Executive Officer

Dated: September 29,  1998           CUSTOM PRINTING COMPANY

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        Chief Executive Officer

Dated: September 29,  1998           MARINE MIDLAND BANK,
                                        as Trustee

                                     By: /s/ Marcia Markowski
                                        ----------------------------------------
                                        Name:  Marcia Markowski
                                        Title: Assistant Vice President

[Signature page to Fifth Supplemental Indenture, dated September ___, 1998,
among Von Hoffmann Press, Inc., ET. AL., and Marine Midland Bank, as Trustee.]

                                        4

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00041-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00041-of-00352.parquet"}]]