Merchants can't see very far. Escorts can see farther then merchants. Capital warships and cruisers, can see father still.
During daylight hours, if your not far enough way, the escorts will see you. Your lookouts can see farther then the escorts can. So you should be able to keep in contact by running a bit farther out.
During nightime, all AI units can see about 60% of the distance they normally could. Presenting a large profile, and runnning at high speeds are ways to get yourself detected. Always try to approach, presenting only your bow, and keep your speed down to say, 10 kts or less.
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