When you update help and specify the verbose switch you see messages similar to the following:
PS> Update-Help -Verbose -Force
VERBOSE: Your connection has been redirected to the following URI:
VERBOSE: Microsoft.PowerShell.Utility: Updated
C:\Windows\System32\WindowsPowerShell\v1.0\en-US\Microsoft.PowerShell.Commands.Utility.dll-help.xml. Culture en-US
Based on these messages I can see that the Utility module file has a new version, 220.127.116.11, and it was updated successfully.
If I run Update-Help again (and again) I get the same messages which doesn't make sense at all. If a file was updated the first time why it appears as updated in subsequent executions?