In general WinSCP can do this.

You can start here:
https://winscp.net/eng/docs/guide_automation

Note while WinSCP can resume interrupted file transfers, it cannot resume script at any point (like when the connection gets lost during login). So it may, although rarely happen, that the script does not resume when you loose connection.

Though you can always re-run the script, when it fails. You can detect that by WinSCP exit code:
https://winscp.net/eng/docs/guide_automation#results
https://winscp.net/eng/docs/script_retry

I just came across WinSCP and am looking to see if it will do what I am looking for. The situation is this... I have a fleet of about 30-40 laptops in cars each running several different applications. For one of the applications, I need to update a 2 files daily and for the other applications I need to push out updates much less frequently.

I am looking to set this up so that when a user turns on the computer and logs in, it checks for and downloads/synchronizes the files automatically with little or no user intervention.

The other issue is that these laptops use Verizon wireless 3G/4G modems so bandwidth and latency can be an issue (although the majority of the files are usually no more than a few megs) as well as total loss of connectivity from time to time. If the laptop looses connectivity during a file transfer, I need to manage that somehow to ensure the file gets transferred once connectivity returns. Note that I am not very familiar with scripting; I can handle a simple batch file, but beyond that I'd need assistance.

Thanks in advance for any input.

By the way, we use a Verizon Private Network so all the laptops use a LAN address that gets NAT'ed so they appear to be and pretty much function as if they were on our LAN.

So the big question is... am I looking in the right place? Can WinSCP handle these functions?