Based on your description, this is not a Windows problem — it’s almost certainly a power / battery hardware issue on your Surface device.
Replace the battery to fix the problem.
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I need to press the power button very long or multiple times before it shows the windows logo and starts. The behavior is tied to a clear battery charge threshold (~80%):
When the AC adapter is connected, the device always powers on correctly on the first press.
Answer accepted by question author
Based on your description, this is not a Windows problem — it’s almost certainly a power / battery hardware issue on your Surface device.
Replace the battery to fix the problem.