As a GUI fetishist, I sometimes think the command prompt's only right to exist is the ping command. It is not that there are no GUI tools for ping. I already reviewed two in the past (eToolz, FREEping). But somehow after working with such a tool for a while, I come back to the command prompt. Perhaps it is not that easy to change a decade-old habit. From a rational point of view, it certainly makes sense to use a GUI-based ping tool.
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For one thing, you don't have to remember the ping syntax if you need a special parameter. For instance, if you want ping a host until you stop the command (parameter -t), you can just click on the corresponding option. Moreover, the output looks nicer and most important you don't have to type "ping". Considering how often you will have to type these four letters in your IT career without a GUI tool, this could mount up to a whole novel which you could have typed instead. 😉
WinPing has a few other nice features: Multiple-hosts ping, export ping results, real-time graphical chart, average response time, and country codes. The Help Desk Geek has a more detailed review of WinPing.