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I work on an application that is mainly used in locations that don't have internet access during operation, but every night or so the equipment is brought back to a location where data connection is possible.
If the loupe SaaS platform is used, is it capable of automatically uploading log details when connection is detected without requiring user initiation?
Absolutely! That's an automatic built-in behavior. Basically, Loupe always records data to local session fragments and then uploads that when a connection is available and it is allowed to upload (so you can control when that is, as well as just leave it on automatic and it'll probe for a valid connection in the background).
In your case what you might want to do is use the Packager utility when you are doing your maintenance operation to force data to be pushed at that exact moment. The Packager utility can be run standalone from the command line or it can be configured to provide a GUI for a user.