[snippy_about_it]

'I have all the plans of the rebels...'

-- General George McClellan
in a telegram to Lincoln, September 13, 1862

'That omission to deliver in his [the courier's] case so important an order [would] have been recollected as entailing the duty to advise its loss, to guard against consequences, and to act as required... But I could not of course say positively that I had sent any particular courier to him [D.H. Hill] after such a lapse of time.'

-- Robert Hall Chilton
December 8, 1874
(Lee's Adjutant General who signed the lost copy of Special Orders 191)

[snippy_about_it]

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[PhilDragoo]

The Ryans point especially to the Battle of Antietam on 16th-18th September 1862 as the "most catastrophic" (and in the end pivotal) example of Confederate cryptological negligence. This was a supremely violent battle in which the Union General George B. McClellan had to blunt a multi-column advance by Confederate General Robert E. Lee, and by the time it was all over there had been twice as many casualties as in the 1812, Mexican, and Spanish-American Wars put together, and four times as many as were suffered during the D-Day landings 82 years later. The intercept on this occasion was very low tech - nothing more complex than the loss from an unknown Confederate staff officer's pocket of an en clair copy of General Lee's special order #191 for the invasion of Maryland.

ASIDE: The Confederates were in fact thrice negligent at Antietam, (a) for not enciphering the order in the first place, (b) for simply losing it, and (c) for not monitoring their enemy's newspapers (specifically, for failing to abort their attack after the New York Herald had stupidly reported the intercept on 15th September); in fact, Robert E. Lee subsequently claimed that he only learned of the loss early the following year (Fishel, 1996).

From Codes and Ciphers in History, Part 2 - 1853 to 1917