It’s going to be a timing race issue, I’m sure. Subtle changes in the events processing requested will affect who wins each “race”.
Not directly connected, but I can report that us Window users do throw up a bunch of timing problems that most openHAB (Pi based) users never see, purely because of power of the host.
As @Kim_Andersen says, these are “ordinary enough” warnings and not connected to the ‘falling silent’ stoppage issue at hand.
The retry always seems to work, so it’s not serious. Most likely due to hammering the target with TCP disconnect/reconnect cycles. If you want to address this see -
I would recommend read the whole thing anyway if you expect to use a 250mS poll cycle ordinarily.