fix: prevent nested condensing from including previously-condensed content

src/core/condense/__tests__/condense.spec.ts

@@ -250,7 +250,7 @@ Line 2
 		it("should not summarize messages that already contain a recent summary with no new messages", async () => {
 			const messages: ApiMessage[] = [
 				{ role: "user", content: "First message with /command" },
-				{ role: "assistant", content: "Previous summary", isSummary: true },
+				{ role: "user", content: "Previous summary", isSummary: true },
 			]
 
 			const result = await summarizeConversation(messages, mockApiHandler, "System prompt", taskId, false)
@@ -413,20 +413,5 @@ Line 2
 			expect(result[1]).toEqual(messages[4])
 			expect(result[2]).toEqual(messages[5])
 		})
-
-		it("should prepend first user message when summary starts with assistant", () => {
-			const messages: ApiMessage[] = [
-				{ role: "user", content: "Original first message" },
-				{ role: "assistant", content: "Summary content", isSummary: true },
-				{ role: "user", content: "After summary" },
-			]
-
-			const result = getMessagesSinceLastSummary(messages)
-
-			// Should prepend original first message for Bedrock compatibility
-			expect(result[0]).toEqual(messages[0]) // Original first user message
-			expect(result[1]).toEqual(messages[1]) // The summary
-			expect(result[2]).toEqual(messages[2])
-		})
 	})
 })

src/core/condense/__tests__/index.spec.ts

@@ -252,38 +252,36 @@ describe("getMessagesSinceLastSummary", () => {
 		expect(result).toEqual(messages)
 	})
 
-	it("should return messages since the last summary (preserves original first user message when needed)", () => {
+	it("should return messages since the last summary", () => {
 		const messages: ApiMessage[] = [
 			{ role: "user", content: "Hello", ts: 1 },
 			{ role: "assistant", content: "Hi there", ts: 2 },
-			{ role: "assistant", content: "Summary of conversation", ts: 3, isSummary: true },
-			{ role: "user", content: "How are you?", ts: 4 },
-			{ role: "assistant", content: "I'm good", ts: 5 },
+			{ role: "user", content: "Summary of conversation", ts: 3, isSummary: true },
+			{ role: "assistant", content: "How are you?", ts: 4 },
+			{ role: "user", content: "I'm good", ts: 5 },
 		]
 
 		const result = getMessagesSinceLastSummary(messages)
 		expect(result).toEqual([
-			{ role: "user", content: "Hello", ts: 1 },
-			{ role: "assistant", content: "Summary of conversation", ts: 3, isSummary: true },
-			{ role: "user", content: "How are you?", ts: 4 },
-			{ role: "assistant", content: "I'm good", ts: 5 },
+			{ role: "user", content: "Summary of conversation", ts: 3, isSummary: true },
+			{ role: "assistant", content: "How are you?", ts: 4 },
+			{ role: "user", content: "I'm good", ts: 5 },
 		])
 	})
 
 	it("should handle multiple summary messages and return since the last one", () => {
 		const messages: ApiMessage[] = [
 			{ role: "user", content: "Hello", ts: 1 },
-			{ role: "assistant", content: "First summary", ts: 2, isSummary: true },
-			{ role: "user", content: "How are you?", ts: 3 },
-			{ role: "assistant", content: "Second summary", ts: 4, isSummary: true },
-			{ role: "user", content: "What's new?", ts: 5 },
+			{ role: "user", content: "First summary", ts: 2, isSummary: true },
+			{ role: "assistant", content: "How are you?", ts: 3 },
+			{ role: "user", content: "Second summary", ts: 4, isSummary: true },
+			{ role: "assistant", content: "What's new?", ts: 5 },
 		]
 
 		const result = getMessagesSinceLastSummary(messages)
 		expect(result).toEqual([
-			{ role: "user", content: "Hello", ts: 1 },
-			{ role: "assistant", content: "Second summary", ts: 4, isSummary: true },
-			{ role: "user", content: "What's new?", ts: 5 },
+			{ role: "user", content: "Second summary", ts: 4, isSummary: true },
+			{ role: "assistant", content: "What's new?", ts: 5 },
 		])
 	})
 

src/core/condense/__tests__/nested-condense.spec.ts

@@ -0,0 +1,211 @@
+import { describe, it, expect } from "vitest"
+import { ApiMessage } from "../../task-persistence/apiMessages"
+import { getEffectiveApiHistory, getMessagesSinceLastSummary } from "../index"
+
+describe("nested condensing scenarios", () => {
+	describe("fresh-start model (user-role summaries)", () => {
+		it("should return only the latest summary and messages after it", () => {
+			const condenseId1 = "condense-1"
+			const condenseId2 = "condense-2"
+
+			// Simulate history after two nested condenses with user-role summaries
+			const history: ApiMessage[] = [
+				// Original task - condensed in first condense
+				{ role: "user", content: "Build an app", ts: 100, condenseParent: condenseId1 },
+				// Messages from first condense
+				{ role: "assistant", content: "Starting...", ts: 200, condenseParent: condenseId1 },
+				{ role: "user", content: "Add auth", ts: 300, condenseParent: condenseId1 },
+				// First summary (user role, fresh-start model) - then condensed in second condense
+				{
+					role: "user",
+					content: [{ type: "text", text: "## Summary 1" }],
+					ts: 399,
+					isSummary: true,
+					condenseId: condenseId1,
+					condenseParent: condenseId2, // Tagged during second condense
+				},
+				// Messages after first condense but before second
+				{ role: "assistant", content: "Auth added", ts: 400, condenseParent: condenseId2 },
+				{ role: "user", content: "Add database", ts: 500, condenseParent: condenseId2 },
+				// Second summary (user role, fresh-start model)
+				{
+					role: "user",
+					content: [{ type: "text", text: "## Summary 2" }],
+					ts: 599,
+					isSummary: true,
+					condenseId: condenseId2,
+				},
+				// Messages after second condense (kept messages)
+				{ role: "assistant", content: "Database added", ts: 600 },
+				{ role: "user", content: "Now test it", ts: 700 },
+			]
+
+			// Step 1: Get effective history
+			const effectiveHistory = getEffectiveApiHistory(history)
+
+			// Should only contain: Summary2, and messages after it
+			expect(effectiveHistory.length).toBe(3)
+			expect(effectiveHistory[0].isSummary).toBe(true)
+			expect(effectiveHistory[0].condenseId).toBe(condenseId2) // Latest summary
+			expect(effectiveHistory[1].content).toBe("Database added")
+			expect(effectiveHistory[2].content).toBe("Now test it")
+
+			// Verify NO condensed messages are included
+			const hasCondensedMessages = effectiveHistory.some(
+				(msg) => msg.condenseParent && history.some((m) => m.isSummary && m.condenseId === msg.condenseParent),
+			)
+			expect(hasCondensedMessages).toBe(false)
+
+			// Step 2: Get messages since last summary (on effective history)
+			const messagesSinceLastSummary = getMessagesSinceLastSummary(effectiveHistory)
+
+			// Should be the same as effective history since Summary2 is already at the start
+			expect(messagesSinceLastSummary.length).toBe(3)
+			expect(messagesSinceLastSummary[0].isSummary).toBe(true)
+			expect(messagesSinceLastSummary[0].condenseId).toBe(condenseId2)
+
+			// CRITICAL: No previous history (Summary1 or original task) should be included
+			const hasSummary1 = messagesSinceLastSummary.some((m) => m.condenseId === condenseId1)
+			expect(hasSummary1).toBe(false)
+
+			const hasOriginalTask = messagesSinceLastSummary.some((m) => m.content === "Build an app")
+			expect(hasOriginalTask).toBe(false)
+		})
+
+		it("should handle triple nested condense correctly", () => {
+			const condenseId1 = "condense-1"
+			const condenseId2 = "condense-2"
+			const condenseId3 = "condense-3"
+
+			const history: ApiMessage[] = [
+				// First condense content
+				{ role: "user", content: "Task", ts: 100, condenseParent: condenseId1 },
+				{
+					role: "user",
+					content: [{ type: "text", text: "## Summary 1" }],
+					ts: 199,
+					isSummary: true,
+					condenseId: condenseId1,
+					condenseParent: condenseId2,
+				},
+				// Second condense content
+				{ role: "assistant", content: "After S1", ts: 200, condenseParent: condenseId2 },
+				{
+					role: "user",
+					content: [{ type: "text", text: "## Summary 2" }],
+					ts: 299,
+					isSummary: true,
+					condenseId: condenseId2,
+					condenseParent: condenseId3,
+				},
+				// Third condense content
+				{ role: "assistant", content: "After S2", ts: 300, condenseParent: condenseId3 },
+				{
+					role: "user",
+					content: [{ type: "text", text: "## Summary 3" }],
+					ts: 399,
+					isSummary: true,
+					condenseId: condenseId3,
+				},
+				// Current messages
+				{ role: "assistant", content: "Current work", ts: 400 },
+			]
+
+			const effectiveHistory = getEffectiveApiHistory(history)
+
+			// Should only contain Summary3 and current work
+			expect(effectiveHistory.length).toBe(2)
+			expect(effectiveHistory[0].condenseId).toBe(condenseId3)
+			expect(effectiveHistory[1].content).toBe("Current work")
+
+			const messagesSinceLastSummary = getMessagesSinceLastSummary(effectiveHistory)
+			expect(messagesSinceLastSummary.length).toBe(2)
+
+			// No previous summaries should be included
+			const hasPreviousSummaries = messagesSinceLastSummary.some(
+				(m) => m.condenseId === condenseId1 || m.condenseId === condenseId2,
+			)
+			expect(hasPreviousSummaries).toBe(false)
+		})
+	})
+
+	describe("getMessagesSinceLastSummary behavior with full vs effective history", () => {
+		it("should return consistent results when called with full history vs effective history", () => {
+			const condenseId = "condense-1"
+
+			const fullHistory: ApiMessage[] = [
+				{ role: "user", content: "Original task", ts: 100, condenseParent: condenseId },
+				{ role: "assistant", content: "Response", ts: 200, condenseParent: condenseId },
+				{
+					role: "user",
+					content: [{ type: "text", text: "Summary" }],
+					ts: 299,
+					isSummary: true,
+					condenseId,
+				},
+				{ role: "assistant", content: "After summary", ts: 300 },
+			]
+
+			// Called with FULL history (as in summarizeConversation)
+			const fromFullHistory = getMessagesSinceLastSummary(fullHistory)
+
+			// Called with EFFECTIVE history (as in attemptApiRequest)
+			const effectiveHistory = getEffectiveApiHistory(fullHistory)
+			const fromEffectiveHistory = getMessagesSinceLastSummary(effectiveHistory)
+
+			// Both should return the same messages when summary is user role
+			expect(fromFullHistory.length).toBe(fromEffectiveHistory.length)
+
+			// Both should start with the summary
+			expect(fromFullHistory[0].isSummary).toBe(true)
+			expect(fromEffectiveHistory[0].isSummary).toBe(true)
+		})
+
+		it("should not include condensed original task in effective history", () => {
+			const condenseId1 = "condense-1"
+			const condenseId2 = "condense-2"
+
+			// Scenario: Two nested condenses with user-role summaries
+			const fullHistory: ApiMessage[] = [
+				{ role: "user", content: "Original task - should NOT appear", ts: 100, condenseParent: condenseId1 },
+				{ role: "assistant", content: "Old response", ts: 200, condenseParent: condenseId1 },
+				// First summary (user role, fresh-start model), then condensed again
+				{
+					role: "user",
+					content: [{ type: "text", text: "Summary 1" }],
+					ts: 299,
+					isSummary: true,
+					condenseId: condenseId1,
+					condenseParent: condenseId2,
+				},
+				{ role: "assistant", content: "After S1", ts: 300, condenseParent: condenseId2 },
+				// Second summary (user role, fresh-start model)
+				{
+					role: "user",
+					content: [{ type: "text", text: "Summary 2" }],
+					ts: 399,
+					isSummary: true,
+					condenseId: condenseId2,
+				},
+				{ role: "assistant", content: "Current message", ts: 400 },
+			]
+
+			const effectiveHistory = getEffectiveApiHistory(fullHistory)
+			expect(effectiveHistory.length).toBe(2) // Summary2 + Current message
+
+			const messagesSinceLastSummary = getMessagesSinceLastSummary(effectiveHistory)
+
+			// The original task should NOT be included
+			const hasOriginalTask = messagesSinceLastSummary.some((m) =>
+				typeof m.content === "string"
+					? m.content.includes("Original task")
+					: JSON.stringify(m.content).includes("Original task"),
+			)
+			expect(hasOriginalTask).toBe(false)
+
+			// Summary1 should not be included (it was condensed)
+			const hasSummary1 = messagesSinceLastSummary.some((m) => m.condenseId === condenseId1)
+			expect(hasSummary1).toBe(false)
+		})
+	})
+})