File completions work for Import and Get but not with << syntax as you can see:
Is there some way to enable this?
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$\begingroup$ No, there isn't. See the link to the WTC2015 talk by John Fultz I posted on your other question. $\endgroup$ – Szabolcs Sep 26 '16 at 9:01
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No, this isn't possible as of version 11.0.0.
Since version 9.0.1, auto-completion is handled by a separate service kernel process which is for the exclusive use of the front end and is not user-programmable.
At the WTC 2015, John Fultz showed a prototype of user-programmable auto-completion, but this doesn't seem to be present in version 11.0.0 yet.
