fix: include initial ask in condense summarization (#8293)

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

@@ -283,6 +283,32 @@ describe("summarizeConversation", () => {
 		const mockCallArgs = (maybeRemoveImageBlocks as Mock).mock.calls[0][0] as any[]
 		expect(mockCallArgs[mockCallArgs.length - 1]).toEqual(expectedFinalMessage)
 	})
+	it("should include the original first user message in summarization input", async () => {
+		const messages: ApiMessage[] = [
+			{ role: "user", content: "Initial ask", ts: 1 },
+			{ role: "assistant", content: "Ack", ts: 2 },
+			{ role: "user", content: "Follow-up", ts: 3 },
+			{ role: "assistant", content: "Response", ts: 4 },
+			{ role: "user", content: "More", ts: 5 },
+			{ role: "assistant", content: "Later", ts: 6 },
+			{ role: "user", content: "Newest", ts: 7 },
+		]
+
+		await summarizeConversation(messages, mockApiHandler, defaultSystemPrompt, taskId, DEFAULT_PREV_CONTEXT_TOKENS)
+
+		const mockCallArgs = (maybeRemoveImageBlocks as Mock).mock.calls[0][0] as any[]
+
+		// Expect the original first user message to be present in the messages sent to the summarizer
+		const hasInitialAsk = mockCallArgs.some(
+			(m) =>
+				m.role === "user" &&
+				(typeof m.content === "string"
+					? m.content === "Initial ask"
+					: Array.isArray(m.content) &&
+						m.content.some((b: any) => b.type === "text" && b.text === "Initial ask")),
+		)
+		expect(hasInitialAsk).toBe(true)
+	})
 
 	it("should calculate newContextTokens correctly with systemPrompt", async () => {
 		const messages: ApiMessage[] = [

src/core/condense/index.ts

@@ -17,8 +17,7 @@ This summary should be thorough in capturing technical details, code patterns, a
 
 Your summary should be structured as follows:
 Context: The context to continue the conversation with. If applicable based on the current task, this should include:
-  1. Previous Conversation: High level details about what was discussed throughout the entire conversation with the user. This should be written to allow someone to be able to follow the general overarching conversation flow.
-  2. Current Work: Describe in detail what was being worked on prior to this request to summarize the conversation. Pay special attention to the more recent messages in the conversation.
+  1. Previous Conversation: High level details about what was discussed throughout the entire conversation with the user. This should be written to allow someone to be able to follow the general overarching conversation flow.  2. Current Work: Describe in detail what was being worked on prior to this request to summarize the conversation. Pay special attention to the more recent messages in the conversation.
   3. Key Technical Concepts: List all important technical concepts, technologies, coding conventions, and frameworks discussed, which might be relevant for continuing with this work.
   4. Relevant Files and Code: If applicable, enumerate specific files and code sections examined, modified, or created for the task continuation. Pay special attention to the most recent messages and changes.
   5. Problem Solving: Document problems solved thus far and any ongoing troubleshooting efforts.
@@ -103,8 +102,8 @@ export async function summarizeConversation(
 
 	// Always preserve the first message (which may contain slash command content)
 	const firstMessage = messages[0]
-	// Get messages to summarize, excluding the first message and last N messages
-	const messagesToSummarize = getMessagesSinceLastSummary(messages.slice(1, -N_MESSAGES_TO_KEEP))
+	// Get messages to summarize, including the first message and excluding the last N messages
+	const messagesToSummarize = getMessagesSinceLastSummary(messages.slice(0, -N_MESSAGES_TO_KEEP))
 
 	if (messagesToSummarize.length <= 1) {
 		const error =