diff --git a/src/core/condense/__tests__/index.test.ts b/src/core/condense/__tests__/index.test.ts
index 86575b85ba..e06ea4197d 100644
--- a/src/core/condense/__tests__/index.test.ts
+++ b/src/core/condense/__tests__/index.test.ts
@@ -205,7 +205,6 @@ describe("summarizeConversation", () => {
 		expect(result.messages).toEqual(messages)
 		expect(result.cost).toBe(0.02)
 		expect(result.summary).toBe("")
-		expect(result.newContextTokens).toBe(100) // Only from countTokens since outputTokens is 0
 		expect(mockWarn).toHaveBeenCalledWith("Received empty summary from API")
 
 		// Restore console.warn
diff --git a/src/core/condense/index.ts b/src/core/condense/index.ts
index 48d246907e..5ec839d05c 100644
--- a/src/core/condense/index.ts
+++ b/src/core/condense/index.ts
@@ -70,10 +70,10 @@ export async function summarizeConversation(
 		return response // Not enough messages to warrant a summary
 	}
 	const keepMessages = messages.slice(-N_MESSAGES_TO_KEEP)
-	for (const message of keepMessages) {
-		if (message.isSummary) {
-			return response // We recently summarized these messages; it's too soon to summarize again.
-		}
+	// Check if there's a recent summary in the messages we're keeping
+	const recentSummaryExists = keepMessages.some((message) => message.isSummary)
+	if (recentSummaryExists) {
+		return response // We recently summarized these messages; it's too soon to summarize again.
 	}
 	const finalRequestMessage: Anthropic.MessageParam = {
 		role: "user",