Yeah, sorry..., that's not shown, but is happening down the bottom after the 'day and time' - before the SENT or FAILED outcome.
Those response messages are returned from the OK string.
Basically, everything throws 'OK', all the way down - including +CSMTPSSEND on the first pass...
Which makes me think the 'send' is working, but the modem is sitting on the message - hence the second attempt fails (until a power cycle is completed)
Thanks for looking!