diff --git a/src/core/assistant-message/presentAssistantMessage.ts b/src/core/assistant-message/presentAssistantMessage.ts
index 344af8bfcc..ca922df543 100644
--- a/src/core/assistant-message/presentAssistantMessage.ts
+++ b/src/core/assistant-message/presentAssistantMessage.ts
@@ -82,7 +82,7 @@ export async function presentAssistantMessage(cline: Task) {
 
 	switch (block.type) {
 		case "text": {
-			if (cline.didRejectTool || cline.didAlreadyUseTool) {
+			if (cline.didRejectTool) {
 				break
 			}
 
@@ -235,8 +235,9 @@ export async function presentAssistantMessage(cline: Task) {
 				break
 			}
 
-			if (cline.didAlreadyUseTool) {
+			if (cline.didAlreadyUseTool && block.name !== "update_todo_list") {
 				// Ignore any content after a tool has already been used.
+				// Exception: update_todo_list can be used multiple times
 				cline.userMessageContent.push({
 					type: "text",
 					text: `Tool [${block.name}] was not executed because a tool has already been used in this message. Only one tool may be used per message. You must assess the first tool's result before proceeding to use the next tool.`,
@@ -256,8 +257,7 @@ export async function presentAssistantMessage(cline: Task) {
 
 				// Once a tool result has been collected, ignore all other tool
 				// uses since we should only ever present one tool result per
-				// message. Exception: update_todo_list is allowed to be followed
-				// by text content.
+				// message. Exception: update_todo_list can be used multiple times.
 				if (block.name !== "update_todo_list") {
 					cline.didAlreadyUseTool = true
 				}
@@ -554,7 +554,12 @@ export async function presentAssistantMessage(cline: Task) {
 	// skip execution since `didRejectTool` and iterate until `contentIndex` is
 	// set to message length and it sets userMessageContentReady to true itself
 	// (instead of preemptively doing it in iterator).
-	if (!block.partial || cline.didRejectTool || cline.didAlreadyUseTool) {
+	if (
+		!block.partial ||
+		cline.didRejectTool ||
+		(cline.didAlreadyUseTool && block.type !== "tool_use") ||
+		(cline.didAlreadyUseTool && block.type === "tool_use" && block.name !== "update_todo_list")
+	) {
 		// Block is finished streaming and executing.
 		if (cline.currentStreamingContentIndex === cline.assistantMessageContent.length - 1) {
 			// It's okay that we increment if !didCompleteReadingStream, it'll
diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 53b8ef5b87..112b711629 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -1427,7 +1427,13 @@ export class Task extends EventEmitter<ClineEvents> {
 					// get generation details.
 					// UPDATE: It's better UX to interrupt the request at the
 					// cost of the API cost not being retrieved.
-					if (this.didAlreadyUseTool) {
+					// Exception: update_todo_list can be used multiple times
+					// Check if any update_todo_list is being processed (partial or complete)
+					const hasUpdateTodoList = this.assistantMessageContent.some(
+						(block) => block.type === "tool_use" && block.name === "update_todo_list",
+					)
+
+					if (this.didAlreadyUseTool && !hasUpdateTodoList) {
 						assistantMessage +=
 							"\n\n[Response interrupted by a tool use result. Only one tool may be used at a time and should be placed at the end of the message.]"
 						break