Live update stuck pending if initiated too soon after boot

Over the past few years I've cultivated a habit of manually initiating Live Update immediately upon booting my PC.  For some time now I've noticed that if I do this too soon, the Live Update window pops up and shows Check for Updates in a pending state.  Live Update will stall on me at that point and not complete until I cancel it and try again (sometimes if I'm in too big of a hurry it may take more than one retry).  Currently this occurs under Win10 but I had it happen rather regularly under Win7 before I upgraded.  This isn't a big problem but is enough of an annoyance that I wish someone in Support would look to see why this becomes an unending stall.