Thanks and apologies, Chaley. I missed your reply before my followup post.
I was following a how-to based on sending a book to a Device's and then selecting Main Memory. Not copying the book files into a directory, although the interesting thing is Calibre did transfer files in my example. The catch was CC not recognizing what happened.
Your suggestion to use the Copy to Library function is better. Simpler and more logical without dealing with connecting and ejecting a "device". And, Copy to Library gets a previously empty directory recognized by CC.
Still wonder why zero time elapsed in the Calibre Jobs log.
P.S.
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I need to ask: if you are using Send to folder then why not use CC's wireless device connection and send directly to CC?
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Not using wireless on the Calibre's server. I did try the Content Server on a local network, but the Dropbox approach seemed better in my case.