Greg:

I did not have this issue with the above code saved as a FreeCDF file using CDFPreview. At each opening of the CDF file the data was updated.

The following is tangential to your immediate issue you wish solved.

DynamicModule[{t = None}, 
 Column[{Dynamic[
    ActionMenu[
     "Update Time:", {"On" :> (t = (UpdateInterval -> 1);), 
      "Off" :> (t = None;)}, Method -> "Queued"]], 
   Dynamic[Refresh[
     Row[{ClockGauge[AbsoluteTime[TimeZone -> 0], 
        PlotLabel -> Style["Student", Large, Bold]], 
       ClockGauge[
        AbsoluteTime[
         DateList[
          Lookup[Association[
            Values[URLRead[
               HTTPRequest["http://www.google.com"]][{"Headers"}]]], 
           "date"]]], PlotLabel -> Style["Server", Large, Bold]]}], 
     t]]}, Alignment -> Center]]

Now this worked each time I open the cdf file. It is a bit slow upon opening the first time. But it updates. The external URL is different from the above. But HTTPRequest seems to work in a CDF file. I am not using CDF Player. Other ideas are DockedCells, Using CloudDeploy or APIFunction to deploy an API call that returns a current timestamp. There are examples in the documentation.

Perhaps something along the lines of

TrueQ[PacletManager`$AllowInternet] &&
FreeQ[PingTime["www.wolfram.com"], $TimedOut | $Failed]

can be used to check for connectivity.

Hey Hans, Sorry for the late reply. Thanks for this. It's clever. In tinkering with it, however, I've found that the initialization doesn't pick up the current date and time. It works one time, but not when I relaunch the CDF. Could it be that CDFs are not "allowed" to import from URLs? Greg