If that is the box you had to uncheck to make this work, you likely have some sort of certificate issue on the the tablet. What specifically is harder to tell. If you are using a custom or the auto generated, perhaps the right root is not installed or up to date on that tablet. If you are doing something self signed it would need to be present in the tablets roots.
There could be some other corner case issues, but you'd have to look at the logs on the device.
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