diff --git a/test/cli/watch/watch-missing-module.test.ts b/test/cli/watch/watch-missing-module.test.ts
new file mode 100644
index 0000000000..23952fa1d1
--- /dev/null
+++ b/test/cli/watch/watch-missing-module.test.ts
@@ -0,0 +1,116 @@
+import { expect, test } from "bun:test";
+import fs from "fs";
+import { bunEnv, bunExe, tempDir } from "harness";
+import { join } from "path";
+
+test("watch mode should poll and reload when a missing required file is created", async () => {
+  using dir = tempDir("watch-missing-module", {
+    "file1.ts": `
+      import { message } from "./file2.ts";
+      console.log("SUCCESS:", message);
+    `,
+  });
+
+  // Start bun in watch mode (file2.ts doesn't exist yet)
+  await using proc = Bun.spawn({
+    cmd: [bunExe(), "--watch", "file1.ts"],
+    cwd: String(dir),
+    env: bunEnv,
+    stdout: "pipe",
+    stderr: "pipe",
+    stdin: "ignore",
+  });
+
+  let stdout = "";
+  let stderr = "";
+
+  const stdoutReader = (async () => {
+    for await (const chunk of proc.stdout) {
+      stdout += new TextDecoder().decode(chunk);
+    }
+  })();
+
+  const stderrReader = (async () => {
+    for await (const chunk of proc.stderr) {
+      stderr += new TextDecoder().decode(chunk);
+    }
+  })();
+
+  // Wait for polling to start and for output to be captured
+  await Bun.sleep(1500);
+
+  const combined1 = stdout + stderr;
+
+  // Should see the polling message
+  expect(combined1).toContain("Module not found");
+  expect(combined1).toContain("Polling every 50ms");
+
+  // Now create the missing file
+  fs.writeFileSync(join(String(dir), "file2.ts"), `export const message = "Hello from file2!";\n`);
+
+  // Wait for polling to detect it and reload
+  await Bun.sleep(300);
+
+  proc.kill();
+  await Promise.race([proc.exited, Bun.sleep(2000)]);
+
+  await Promise.race([Promise.all([stdoutReader, stderrReader]), Bun.sleep(500)]);
+
+  const combined2 = stdout + stderr;
+
+  // Should see the reload message
+  // Note: The actual "SUCCESS" output happens after the process restart,
+  // which creates a new process that we can't capture in this test.
+  // But we can verify that the polling detected the file and triggered reload.
+  expect(combined2).toContain("now exists, reloading");
+}, 10000);
+
+test("watch mode should handle relative path imports that don't exist", async () => {
+  using dir = tempDir("watch-missing-relative", {
+    "index.ts": `
+      import { data } from "./lib/helper.ts";
+      console.log("LOADED:", data);
+    `,
+  });
+
+  await using proc = Bun.spawn({
+    cmd: [bunExe(), "--watch", "index.ts"],
+    cwd: String(dir),
+    env: bunEnv,
+    stdout: "pipe",
+    stderr: "pipe",
+    stdin: "ignore",
+  });
+
+  let output = "";
+
+  const reader = (async () => {
+    for await (const chunk of proc.stdout) {
+      output += new TextDecoder().decode(chunk);
+    }
+  })();
+
+  const errReader = (async () => {
+    for await (const chunk of proc.stderr) {
+      output += new TextDecoder().decode(chunk);
+    }
+  })();
+
+  await Bun.sleep(1500);
+
+  // Should be polling for the missing file
+  expect(output).toContain("Polling every 50ms");
+
+  // Create the directory and file
+  fs.mkdirSync(join(String(dir), "lib"), { recursive: true });
+  fs.writeFileSync(join(String(dir), "lib", "helper.ts"), `export const data = 42;\n`);
+
+  await Bun.sleep(300);
+
+  proc.kill();
+  await Promise.race([proc.exited, Bun.sleep(2000)]);
+  await Promise.race([Promise.all([reader, errReader]), Bun.sleep(500)]);
+
+  // Should see the reload message
+  expect(output).toContain("now exists, reloading");
+}, 10000);