Check the device driver for the Kindle, that the AZW3 format is selected as an option.
Are you getting a conversion error as well? Which ends in:
Code:
Traceback (most recent call last):
File "site.py", line 51, in main
File "/home/eschwartz/git/calibre/src/calibre/utils/ipc/worker.py", line 195, in main
result = func(*args, **kwargs)
File "/home/eschwartz/git/calibre/src/calibre/gui2/convert/gui_conversion.py", line 31, in gui_convert_override
override_input_metadata=True)
File "/home/eschwartz/git/calibre/src/calibre/gui2/convert/gui_conversion.py", line 25, in gui_convert
plumber.run()
File "/home/eschwartz/git/calibre/src/calibre/ebooks/conversion/plumber.py", line 1040, in run
accelerators, tdir)
File "/home/eschwartz/git/calibre/src/calibre/customize/conversion.py", line 241, in __call__
log, accelerators)
File "/home/eschwartz/git/calibre/src/calibre/ebooks/conversion/plugins/mobi_input.py", line 43, in convert
opf = os.path.abspath(mr())
File "/home/eschwartz/git/calibre/src/calibre/ebooks/mobi/reader/mobi8.py", line 77, in __call__
self.mobi6_reader.check_for_drm()
File "/home/eschwartz/git/calibre/src/calibre/ebooks/mobi/reader/mobi6.py", line 147, in check_for_drm
raise DRMError(name)
(names of files are using my source code, ignore differences. The general idea is "DRMError".

)
If AZW3 is not selected as compatible with your device (the default is
NOT) calibre cannot send it without converting, and pops up with "WARNING No Suitable Formats".
If the book is DRMed, it will fail to convert with "WARNING Could Not Convert - no suitable formats".
Fix the Kindle Device Driver, and check your tools configuration (or go to the source for help).