diff --git a/coderd/chatd/chatloop/compaction.go b/coderd/chatd/chatloop/compaction.go
index 0d137eb7ab..696698b5dd 100644
--- a/coderd/chatd/chatloop/compaction.go
+++ b/coderd/chatd/chatloop/compaction.go
@@ -17,13 +17,26 @@ const (
 	minCompactionThresholdPercent     = int32(0)
 	maxCompactionThresholdPercent     = int32(100)
 
-	defaultCompactionSummaryPrompt = "Summarize the current chat so a " +
-		"new assistant can continue seamlessly. Include the user's goals, " +
-		"decisions made, concrete technical details (files, commands, APIs), " +
-		"errors encountered and fixes, and open questions. Be dense and factual. " +
-		"Omit pleasantries and next-step suggestions."
-	defaultCompactionSystemSummaryPrefix = "Summary of earlier chat context:"
-	defaultCompactionTimeout             = 90 * time.Second
+	defaultCompactionSummaryPrompt = "You are performing a context compaction. " +
+		"Summarize the conversation so a new assistant can seamlessly " +
+		"continue the work in progress.\n\n" +
+		"Include:\n" +
+		"- The user's overall goal and current task\n" +
+		"- Key decisions made and their rationale\n" +
+		"- Concrete technical details: file paths, function names, " +
+		"commands, APIs, and configurations\n" +
+		"- Errors encountered and how they were resolved\n" +
+		"- Current state of the work: what is DONE, what is IN PROGRESS, " +
+		"and what REMAINS to be done\n" +
+		"- The specific action the assistant was performing or about to " +
+		"perform when this summary was triggered\n\n" +
+		"Be dense and factual. Every sentence should convey essential " +
+		"context for continuation. Do not include pleasantries or " +
+		"conversational filler."
+	defaultCompactionSystemSummaryPrefix = "The following is a summary of " +
+		"the earlier conversation. The assistant was actively working when " +
+		"the context was compacted. Continue the work described below:"
+	defaultCompactionTimeout = 90 * time.Second
 )
 
 type CompactionOptions struct {