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Message: <blockquote data-quote="Guest 7037866" data-source="post: 9578136">IME this depends on the nature of the ambush. In most of my groups, the Point-Man has good enough stealth that if he is in advance of the main party, the ambushers might not even detect him--so he could be ahead of the party when the ambush begins.Single-file in any area over 5-feet wide is rare IMO. Two lines, sometimes even, sometimes staggered, is more natural.Otherwise, who they attack and when also does depend on how much observation they've had. In my example with the hags, they have seen the PCs fight three battles so far:1. Encountering and defeating the werebear--who then asked for their assistance. (Easy victory for PCs)2. The darkling band at the edge of the ruined town. (Easy victory for PCs)3. The quickling patrol inside the town. (Difficult victory, one PC died as was revivified after--PCs needed a short rest).There are still 4-5 more encounters before the PCs encounter the Hags--who will see probably 2 of those battles or receive reports from their spies.As such, the Hags are relatively well-informed of the party's strengths.I don't know about "teachable moments" but I certainly hope my players learn from their mistakes.They try to avoid combat when possible, but often times it simply isn't. What I regret more than anything is their lack of insight sometimes in taking prisoners. The newer players haven't learned that prisoners can lead to intelligence into the enemy camp (so to say) which can be very beneficial.</blockquote>

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