It has the smell of a permissions or corruption issue.

I'd monitor the DTM of stuff in ~/Library while I change some shortcuts, to see 
in which file they get stored.  Then I'd wipe that file completely and start 
over.

> On Apr 5, 2017, at 9:35 AM, Jean-Christophe Helary 
> <[email protected]> wrote:
> 
> Since installing Sierra, I've found that at *each* reboot, the text shortcuts 
> defined in System Preferences > Keyboard > Text are "disabled". They are 
> still there but simply don't work. The only way I've found to "fix" that was 
> to recreate them from scratch (remove them one by one and recreate them one 
> by one). Just "overwriting" them in the Text UI won't do it.
> 
> Do you have any idea why that is?
> 
> Jean-Christophe
> 
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