Here's a case involving the SBA's Office of Hearings and Appeals (OHA) but it has relevance beyond that particular venue. It involves a size protest to the contracting officer and subsequent appeal to OHA.
A size appeal must be filed at OHA within fifteen days of receipt of the size determination. An appellant received the size determination on February 3, 2015 but the appeal petition was not received by OHA until April 9, 2015 and therefore "plainly untimely". Under the relevant regulations, OHA has no discretion to extend or waive the deadline for filing an appeal.
The appellant maintained that it attempted to transmit its appeal by e-mail on February 18, 2015, which would have met the 15 day deadline. It produced an acknowledgement from its e-mail system entitled "Certificate of service." It also contained the phrase "Delivery to these recipients or groups is complete, but no delivery notification was sent by the destination server". There was a problem however in that OHA never received the appeal (or so it maintains).
By regulation, a document must be received at OHA in order to be considered filed. The regulations are clear that an appeal petition is not filed until it is actually received at OHA. SBA regulations provide that although e-mail is a permissible method of delivery, the sender is responsible for ensuring a successful, virus-free transmission, and the sender is encouraged to contact OHA by telephone to verify receipt. Accordingly, having chosen to submit its appeal by e-mail, the appellant was responsible for ensuring that the email successfully reached OHA. The appellant could not reasonably rely solely upon the acknowledgement from its e-mail system, particularly given that the appellant received no response, over a period of several weeks, from OHA.
It is critical to followup e-mail transmissions of important documents with a phone call or some other form of positive assurance, especially on time-critical matters. Do not assume that your and the Government's email systems are infallible.