You can use PowerShell and Windows Task Scheduler to automate various tasks on a Windows system. From within a PowerShell script, it is also easy to ping Healthchecks.
Here is a simple PowerShell script that pings Healthchecks. When scheduled to run with Task Scheduler, it will essentially just send regular "I'm alive" messages. Of course, you can extend it to do more things.
# inside a PowerShell script:
Invoke-RestMethod https://hc.oceanx.org/ping/your-uuid-here
Save the above to e.g., C:\Scripts\healthchecks.ps1.
Then use the following command in a Scheduled Task to run the script:
powershell.exe -ExecutionPolicy bypass -File C:\Scripts\healthchecks.ps1
In simple cases, you can also pass the script to PowerShell directly, using the "-command" argument:
# Without an underlying script, passing the command to PowerShell directly:
powershell.exe -command &{Invoke-RestMethod https://hc.oceanx.org/ping/your-uuid-here}