Take your battery and get it checked, the behavior with the slow jack would indicate it may be due for a replacement.
If your battery is low, when you connect to the trailer the voltages will be thrown off and the controller may not be able to tell if you have brakes or not. The recognition problem will probably go away if your battery is brought back up to full voltage by charging, but you'll also be sacrificing safety if your battery isn't working properly.
In the event of a break-away your trailer battery is what activates the brakes, so if you don't have a working battery then your trailer will not stop on its own.
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2019 White Hawk 26RK
2018 F150 SuperCrew 3.5 EcoBoost
Blue Ox Sway Pro 1000lb WDH
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