WIll the charger continue to top off the device you are charging or do you need to press the button each time you want to charge the device?

I just experimented and once the device is fully charged the battery pack stops charging - it effectively turns off. There is no trickle charge. Even connected, as the connected device loses charge level the battery charger pack will not automatically start charging the device again until the button on the anker is pressed again.

Using 2nd Gen Astro E4 13000mAh 3A High Capacity Fast Portable Charger

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Varies between battery and device.

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Like @nigelhealy said it varies between device and battery being used. I currently use the 20k powercore updated model and it keeps my phone charged and topped up if I use it while it’s plugged in

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Also discovered that depending on the external battery I use, the behavior is not the same. Some batteries activate themselves when plugging the device, some need a press on their button.