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In cooler weather, the battery does not accept a charge as readily as it will in 70+ degree temps. Therefore, the rate of charge accepted will be less than normal.
That assumes the charging system is okay.
If, by way of example, it takes 1 KW of power to start the bike, and you only ride it a short distance and it only receives say maybe 0.2 KW of recharge, then the battery's charge level is still less than when you first started the engine.
If that cycle is repeated for a few times, the battery will eventually be too low to start the engine.
Using a Battery Tender on the bike while it is parked between trips will go a long way towards preventing you getting stranded away from home.
A longer ride of 50 or more miles, the battery should be well topped off.
I rode my bike to work and back daily. A trip that takes 20-30 minutes depending on traffic. Under that regimen, I never had battery problems until the battery aged enough that it just plain sulphated and died.
Make sure to keep the water level at or very close to the full mark. that helps extend the normal life span of a battery.