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I'm looking for a gratis piece of Windows and/or Android software that will ping a list pre-defined (or configurable) sites in order to determine average latency.

By repeating the process numerous times, and taking the median of the averages, I'm hoping to determine a reasonable average latency value. I can do that part by hand, if the software cannot.

The software can by CLI (command line interface) or GUI (graphical user interface).

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How can I ping a list of sites in order to determine average latency?

On Windows you can use PingInfoView (free) by Nirsoft:

PingInfoView is a small utility that allows you to easily ping multiple host names and IP addresses, and watch the result in one table.

It automatically ping to all hosts every number of seconds that you specify, and displays the number of succeed and failed pings, as well as the average ping time.

You can also save the ping result into text/html/xml file, or copy it to the clipboard.

It even works out the average ping time (latency) for you (per site).

Example output:

enter image description here

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Disclaimer

I am not affiliated with Nirsoft in any way, I am just an end user of their software.

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You can do it with PowerShell using the .NET System.Net.NetworkInformation.Ping class.

$PingObj = New-Object System.Net.NetworkInformation.Ping
$PingObj.Send("www.somewebsite.local")

Status        : Success
Address       : 1.1.1.1
RoundtripTime : 70
Options       : System.Net.NetworkInformation.PingOptions
Buffer        : {97, 98, 99, 100...}

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