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Vanguard Windsor/(TM)/ Fund



Supplement to the Prospectus Dated February 27, 2009

In the Investment Advisors section, the text is restated as follows:

The Fund uses a multimanager approach. Each advisor independently manages its
assigned portion of the Fund's assets, subject to the supervision and oversight
of Vanguard and the Fund's board of trustees. The board of trustees designates
the proportion of Fund assets to be managed by each advisor and may change these
proportions at any time.

.. Wellington Management Company, LLP, 75 State Street, Boston, MA 02109, is a
Massachusetts limited liability partnership and an investment counseling firm
that provides investment services to investment companies, employee benefits
plans, endowments, foundations, and other institutions. Wellington Management
and its predecessor organizations have provided investment advisory services for
over 70 years. As of October 31, 2008, Wellington Management had investment
management authority with respect to approximately $427 billion in assets.

.. AllianceBernstein L.P., 1345 Avenue of the Americas, New York, NY 10105, is an
investment advisory firm founded in 1971. As of October 31, 2008,
AllianceBernstein managed approximately $482 billion in assets.

The Fund pays Wellington Management and AllianceBernstein on a quarterly basis.
Each advisor receives a base fee that is based on certain annual percentage
rates applied to average daily net assets managed by the advisor during the most
recent fiscal quarter. The fee paid to each advisor may be increased or
decreased based on the advisor's performance compared with that of a benchmark
index. For these purposes, the cumulative total return of each advisor's portion
of the Fund is compared with that of the S&P 500 Index (for Wellington
Management) or the Russell 1000 Value Index (for AllianceBernstein) over a
trailing 36-month period. Please note that over time, changes in an advisor's
relative performance may result in changes in the performance-based fees paid by
the Fund, which in turn would result in an increase or decrease in the expenses
borne by Fund shareholders.






For the fiscal year ended October 31, 2008, the aggregate advisory fee
represented an effective annual rate of 0.12% of the Fund's average net assets
before a performance-based decrease of 0.03%.

Under the terms of an SEC exemption, the Fund's board of trustees may, without
prior approval from shareholders, change the terms of an advisory agreement or
hire a new investment advisor--either as a replacement for an existing advisor
or as an additional advisor. Any significant change in the Fund's advisory
arrangements will be communicated to shareholders in writing. In addition, as
the Fund's sponsor and overall manager, The Vanguard Group may provide
investment advisory services to the Fund, on an at-cost basis, at any time.
Vanguard may also recommend to the board of trustees that an advisor be hired,
terminated, or replaced, or that the terms of an existing advisory agreement be
revised.

For a discussion of why the board of trustees approved the Fund's investment
advisory agreements, see the most recent semiannual report to shareholders
covering the fiscal period ended April 30.

The managers primarily responsible for the day-to-day management of the
Fund are:

James N. Mordy, Senior Vice President and Equity Portfolio Manager of Wellington
Management. He has worked on the Windsor Fund investment team since 1985; has
managed investment portfolios for Wellington Management since 1997; and has
managed a portion of the Fund since 2008. Education: B.A., Stanford University;
M.B.A., The Wharton School of the University of Pennsylvania.

Joseph G. Paul, Chief Investment Officer of North American Value Equities and
Co-Chief Investment Officer of US Large-Cap Value Equities at AllianceBernstein.
He has worked in investment management since 1987; has managed investment
portfolios for AllianceBernstein since 1999; and has co-managed a portion of the
Fund since September 2009. Education: B.S., University of Arizona; M.S.,
Massachusetts Institute of Technology.

David Yuen, Co-Chief Investment Officer of US Large-Cap Value Equities and
Director of Research--US Value Equities at AllianceBernstein. He has worked in
investment management since 1998; has managed investment portfolios for
AllianceBernstein since 2002; and has co-managed a portion of the Fund since
September 2009. Education: B.S., Columbia University.

The Statement of Additional Information provides information about each
portfolio manager's compensation, other accounts under management, and ownership
of securities in the Fund.


(C) 2009 The Vanguard Group, Inc. All rights reserved.

Vanguard Marketing Corporation, Distributor.                        PS22 092009