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We update via Configuration Manager Software Updates w/o any issues. Can you check if these machines fail to update on auto-update too?
Same here for Chrome updates, we have minimal issues.
One thing I noticed is that if individuals somehow install Chrome from a web site instead of through the controlled installer through Software Center, that it can take a while for the correct version of Chrome we release to install on their PCs. I handle this through collections based on if Chrome is installed on the PC.