TUMBLEWEED COMMUNICATIONS CORP
S-1/A, EX-5.1, 2000-07-21
BUSINESS SERVICES, NEC
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                                                                     EXHIBIT 5.1

                                          July 20, 2000

Tumbleweed Communications Corp.
700 Saginaw Drive
Redwood City, CA 94063

    RE:       TUMBLEWEED COMMUNICATIONS CORP.
              FORM S-1 REGISTRATION STATEMENT
              --------------------------------

Ladies and Gentlemen:

    We have acted as special counsel to Tumbleweed Communications Corp., a
Delaware corporation (the "Company"), in connection with the public offering by
the Company of up to 1,500,000 shares (the "Primary Shares") and the sale of up
to 1,950,000 shares (including 450,000 shares subject to an over-allotment
option) (the "Secondary Shares") by Selling Stockholders as set forth in the
Registration Statement (as hereinafter defined) of the Company's Common Stock,
par value $0.001 per share (the "Common Stock").

    This opinion is being furnished in accordance with the requirements of Item
601(b)(5) of Regulation S-K under the Securities Act of 1933, as amended (the
"Act").

    In connection with this opinion, we have examined originals or copies,
certified or otherwise identified to our satisfaction, of (i) the Registration
Statement on Form S-1 (File No. 33-41188) as filed with the Securities and
Exchange Commission (the "Commission") on July 11, 2000 under the Act, and
Amendment No. 1 to the Registration Statement as filed with the Commission on
July 20, 2000 under the Act (such Registration Statement, as so amended, being
hereinafter referred to as the "Registration Statement"); (ii) the form of the
Underwriting Agreement (the "Underwriting Agreement") proposed to be entered
into between the Company, as issuer, and Credit Suisse First Boston Corporation,
as representatives of the several underwriters named therein (the
"Underwriters"), filed as an exhibit to the Registration Statement; (iii) a
specimen certificate representing the Common Stock; (iv) the Amended and
Restated Certificate of Incorporation of the Company, as presently in effect;
(v) the Amended and Restated Bylaws of the Company, as presently in effect;
(vi) certain resolutions of the Board of Directors of the Company and drafts of
certain resolutions of the Pricing Committee of the Board of Directors of the
Company (the "Pricing Committee") in each case relating to the issuance and sale
of the Primary Shares; and (vii) certain resolutions of the Board of Directors
of the Company relating to the issuance and sale of the Secondary Shares at the
times issued and sold to the Selling Stockholders. We have also examined
originals or copies, certified or otherwise identified to our satisfaction, of
such records of the Company and such agreements, certificates of public
officials, certificates of officers or other representatives of the Company and
others, and such other documents, certificates and records as we have deemed
necessary or appropriate as a basis for the opinions set forth herein.

    In our examination, we have assumed the legal capacity of all natural
persons, the genuineness of all signatures, the authenticity of all documents
submitted to us as originals, the conformity to original documents of all
documents submitted to us as certified, conformed or photostatic copies and the
authenticity of the originals of such latter documents. In making our
examination of documents executed or to be executed by parties other than the
Company, we have assumed that such parties had or will have the power, corporate
or other, to enter into and perform all obligations thereunder and have also
assumed the due authorization by all requisite action, corporate or other, and
execution and delivery by such parties of such documents and the validity and
binding effect thereof. In rendering the opinion set forth in paragraph 2 below,
we have assumed that the Company has received the entire amount of consideration
contemplated by the resolutions of the Board of Directors of the Company
authorizing the issuance of the Secondary Shares. As to any facts material to
the opinions expressed
<PAGE>
Tumbleweed Communications Corp.
July 20, 2000
Page 2

herein which we have not independently established or verified, we have relied
upon statements and representations of officers and other representatives of the
Company and others.

    Members of our firm are admitted to the bar in the State of Delaware, and we
do not express any opinion as to the laws of any other jurisdiction.

    Based upon and subject to the foregoing, we are of the opinion that:

    1.  When (i) the price at which the Primary Shares are to be sold to the
Underwriters pursuant to the Underwriting Agreement and other matters relating
to the issuance and sale of the Primary Shares have been approved by the Pricing
Committee; (ii) the Underwriting Agreement has been duly executed and delivered;
and (iii) the Primary Shares have been delivered to and paid for by the
Underwriters in accordance with the terms of the Underwriting Agreement, the
issuance and sale of the Primary Shares will have been duly authorized, and the
Primary Shares will be validly issued, fully paid and nonassessable.

    2.  The Secondary Shares have been duly authorized and validly issued and
are fully paid and nonassessable.

    We hereby consent to the filing of this opinion with the Commission as an
exhibit to the Registration Statement. We also consent to the reference to our
firm under the caption "Legal Matters" in the Registration Statement. In giving
this consent, we do not thereby admit that we are included in the category of
persons whose consent is required under Section 7 of the Act or the rules and
regulations of the Commission.

                                    Very truly yours,
                                    /s/ SKADDEN ARPS SLATE MEAGHER & FLOM LLP


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