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Based upon the record presented, we conclude that petitioners
cannot avail themselves of the timely mailing/timely filing rule set
forth in section 301.7502-1(c)(1)(iii)(b), Proced. & Admin. Regs.
In the first instance, the controlling regulation contemplates that
the timely mailing/timely filing rule may be invoked where the
petition is delivered to the Court in an envelope or wrapper that
contains a timely private postage meter postmark. The envelope
bearing the petition arrived at the Court without any postmark
indicating the date that it was mailed to the Court. Although we
will allow extrinsic evidence to prove the date of mailing where an
envelope lacks a postmark, see Sylvan v. Commissioner, 65 T.C. 548,
553-555 (1975), there is absolutely no indication that any type of
postage was ever affixed to the envelope. See section 7502(a)(2),
regarding mailing requirements, specifically including the
requirement that postage be prepaid. We are not persuaded by
petitioners' circumstantial evidence that a timely private postage
meter label was properly applied to the envelope.
Even assuming for the sake of argument that petitioners have
proven that the envelope bearing the petition was placed in the mail
with a timely private postage meter postmark of February 28, 2000,
section 301.7502-1(c)(1)(iii)(b), Proced. & Admin. Regs., further
requires that the petition be delivered to the Court within the
ordinary mailing time for that class of mail. We accept Ms.
Vaughan's testimony that the ordinary delivery time for an item
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