Possibly. Once I understand precisely how it works, I'll come back and post... however I doubt you'll need to resend it. Any that I have sent have worked, and always worked their way to the Sent Box in time. Possibly (and this just a guess), "Outbox" means it hasn't been collected. You could test this by checking the status of the PM you sent to me.
"Do not force others, including children, by any means whatsoever, to adopt your views, whether by authority, threat, money, propaganda, or even education." - Ven. Thich Nhat Hanh
"The uprooting of identity is seen by the noble ones as pleasurable; but this contradicts what the whole world sees." (Snp 3.12)
"To argue with a person who has renounced the use of reason is like administering medicine to the dead" - Thomas Paine