Calibre's wireless device can send many files. A few years ago I sent over 2,000 at once to calibre companion (app no longer supported or available).
The problem could be in koreader; calibre has no control over what it does. Or your network might have hiccupped. Or your device went to sleep. Or you ran out of memory. Or space aliens intervened. Without any error messages it is impossible to get past pure speculation.
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