diff --git a/integration-tests/context-compress-interactive.test.ts b/integration-tests/context-compress-interactive.test.ts
index 3a626150f8..f8b318c482 100644
--- a/integration-tests/context-compress-interactive.test.ts
+++ b/integration-tests/context-compress-interactive.test.ts
@@ -24,26 +24,7 @@ describe('Interactive Mode', () => {
       await rig.setup('interactive-compress-test');
 
       const { ptyProcess } = rig.runInteractive();
-
-      let fullOutput = '';
-      ptyProcess.onData((data) => (fullOutput += data));
-
-      const authDialogAppeared = await rig.waitForText(
-        'How would you like to authenticate',
-        5000,
-      );
-
-      // select the second option if auth dialog come's up
-      if (authDialogAppeared) {
-        ptyProcess.write('2');
-      }
-
-      // Wait for the app to be ready
-      const isReady = await rig.waitForText('Type your message', 15000);
-      expect(
-        isReady,
-        'CLI did not start up in interactive mode correctly',
-      ).toBe(true);
+      await rig.ensureReadyForInput(ptyProcess);
 
       const longPrompt =
         'Dont do anything except returning a 1000 token long paragragh with the <name of the scientist who discovered theory of relativity> at the end to indicate end of response. This is a moderately long sentence.';
@@ -74,26 +55,7 @@ describe('Interactive Mode', () => {
       await rig.setup('interactive-compress-test');
 
       const { ptyProcess } = rig.runInteractive();
-
-      let fullOutput = '';
-      ptyProcess.onData((data) => (fullOutput += data));
-
-      const authDialogAppeared = await rig.waitForText(
-        'How would you like to authenticate',
-        5000,
-      );
-
-      // select the second option if auth dialog come's up
-      if (authDialogAppeared) {
-        ptyProcess.write('2');
-      }
-
-      // Wait for the app to be ready
-      const isReady = await rig.waitForText('Type your message', 25000);
-      expect(
-        isReady,
-        'CLI did not start up in interactive mode correctly',
-      ).toBe(true);
+      await rig.ensureReadyForInput(ptyProcess);
 
       await type(ptyProcess, '/compress');
       await new Promise((resolve) => setTimeout(resolve, 100));
diff --git a/integration-tests/test-helper.ts b/integration-tests/test-helper.ts
index 7610c27d7c..440286da31 100644
--- a/integration-tests/test-helper.ts
+++ b/integration-tests/test-helper.ts
@@ -855,4 +855,48 @@ export class TestRig {
 
     return { ptyProcess, promise };
   }
+
+  /**
+   * Waits for an interactive session to be fully ready for input.
+   * This is a higher-level utility to be used with `runInteractive`.
+   *
+   * It handles the initial setup boilerplate:
+   * 1. Automatically handles the authentication prompt if it appears.
+   * 2. Waits for the "Type your message" prompt to ensure the CLI is ready for input.
+   *
+   * Throws an error if the session fails to become ready within the timeout.
+   *
+   * @param ptyProcess The process returned from `runInteractive`.
+   */
+  async ensureReadyForInput(ptyProcess: pty.IPty): Promise<void> {
+    const timeout = 25000;
+    const pollingInterval = 200;
+    const startTime = Date.now();
+    let authPromptHandled = false;
+
+    while (Date.now() - startTime < timeout) {
+      const output = stripAnsi(this._interactiveOutput).toLowerCase();
+
+      // If the ready prompt appears, we're done.
+      if (output.includes('type your message')) {
+        return;
+      }
+
+      // If the auth prompt appears and we haven't handled it yet.
+      if (
+        !authPromptHandled &&
+        output.includes('how would you like to authenticate')
+      ) {
+        ptyProcess.write('2');
+        authPromptHandled = true;
+      }
+
+      // Wait for the next poll.
+      await new Promise((resolve) => setTimeout(resolve, pollingInterval));
+    }
+
+    throw new Error(
+      `CLI did not start up in interactive mode correctly. Output: ${this._interactiveOutput}`,
+    );
+  }
 }