diff --git a/src/core/assistant-message/presentAssistantMessage.ts b/src/core/assistant-message/presentAssistantMessage.ts
index 2e4b3ac4da..65d96a9513 100644
--- a/src/core/assistant-message/presentAssistantMessage.ts
+++ b/src/core/assistant-message/presentAssistantMessage.ts
@@ -852,6 +852,8 @@ export async function presentAssistantMessage(cline: Task) {
 							toolProtocol,
 						})
 					}
+					// Save checkpoint after reading files to preserve context
+					await checkpointSaveAndMark(cline)
 					break
 				case "fetch_instructions":
 					await fetchInstructionsTool.handle(cline, block as ToolUse<"fetch_instructions">, {