diff --git a/packages/core/src/session/runner/to-llm-message.ts b/packages/core/src/session/runner/to-llm-message.ts
index db3ce25fe1a1..e91eef2c28a7 100644
--- a/packages/core/src/session/runner/to-llm-message.ts
+++ b/packages/core/src/session/runner/to-llm-message.ts
@@ -206,7 +206,7 @@ function toLLMMessage(message: SessionMessage.Info, model: ModelV2.Ref, provider
         Message.make({
           id: message.id,
           role: "user",
-          content: `Shell command: ${message.command}\n\n${message.output?.output ?? ""}`,
+          content: `The following shell command was executed by the user:\n\nCommand:\n${message.command}\n\nOutput:\n${message.output?.output ?? ""}`,
           metadata: message.metadata,
         }),
       ]
diff --git a/packages/core/test/session-runner-message.test.ts b/packages/core/test/session-runner-message.test.ts
index 8ddec2fae8e3..fe70ac5943a5 100644
--- a/packages/core/test/session-runner-message.test.ts
+++ b/packages/core/test/session-runner-message.test.ts
@@ -124,7 +124,12 @@ describe("toLLMMessages", () => {
     )
     expect(messages.slice(2).map((message) => message.content)).toEqual([
       [{ type: "text", text: "Synthetic context" }],
-      [{ type: "text", text: "Shell command: pwd\n\n/project" }],
+      [
+        {
+          type: "text",
+          text: "The following shell command was executed by the user:\n\nCommand:\npwd\n\nOutput:\n/project",
+        },
+      ],
       [
         {
           type: "text",