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I’ve been through the depths of the WP and TinyMCE forums on this one and can’t seem to wrap my head around the fixes/patches that closed and resolved the related topics back in the 3.5-3.8 days.
As far as I can tell this is happening within the TinyMCE editors that are inserted using the Advanced Custom Fields plugin (4.4.10). Client is running Chrome 53.0.2785.116. Custom theme based on _underscores.
Selecting text using “Clear Formatting” will work, but unfortunately that also strips out any standard styling within the lists (a not-ideal side effect to an already-not-ideal workaround!)