diff --git a/apps/server/src/routes/worktree/common.ts b/apps/server/src/routes/worktree/common.ts
index 0b2446fc..c58b8f08 100644
--- a/apps/server/src/routes/worktree/common.ts
+++ b/apps/server/src/routes/worktree/common.ts
@@ -13,6 +13,9 @@ import {
 const logger = createLogger("Worktree");
 const execAsync = promisify(exec);
 
+export const AUTOMAKER_INITIAL_COMMIT_MESSAGE =
+  "chore: automaker initial commit";
+
 /**
  * Normalize path separators to forward slashes for cross-platform consistency.
  * This ensures paths from `path.join()` (backslashes on Windows) match paths
@@ -73,3 +76,30 @@ export function logWorktreeError(
 // Re-export shared utilities
 export { getErrorMessageShared as getErrorMessage };
 export const logError = createLogError(logger);
+
+/**
+ * Ensure the repository has at least one commit so git commands that rely on HEAD work.
+ * Returns true if an empty commit was created, false if the repo already had commits.
+ */
+export async function ensureInitialCommit(repoPath: string): Promise<boolean> {
+  try {
+    await execAsync("git rev-parse --verify HEAD", { cwd: repoPath });
+    return false;
+  } catch {
+    try {
+      await execAsync(
+        `git commit --allow-empty -m "${AUTOMAKER_INITIAL_COMMIT_MESSAGE}"`,
+        { cwd: repoPath }
+      );
+      logger.info(
+        `[Worktree] Created initial empty commit to enable worktrees in ${repoPath}`
+      );
+      return true;
+    } catch (error) {
+      const reason = getErrorMessageShared(error);
+      throw new Error(
+        `Failed to create initial git commit. Please commit manually and retry. ${reason}`
+      );
+    }
+  }
+}
diff --git a/apps/server/src/routes/worktree/routes/create.ts b/apps/server/src/routes/worktree/routes/create.ts
index ab44374b..690afe48 100644
--- a/apps/server/src/routes/worktree/routes/create.ts
+++ b/apps/server/src/routes/worktree/routes/create.ts
@@ -12,7 +12,13 @@ import { exec } from "child_process";
 import { promisify } from "util";
 import path from "path";
 import { mkdir } from "fs/promises";
-import { isGitRepo, getErrorMessage, logError, normalizePath } from "../common.js";
+import {
+  isGitRepo,
+  getErrorMessage,
+  logError,
+  normalizePath,
+  ensureInitialCommit,
+} from "../common.js";
 import { trackBranch } from "./branch-tracking.js";
 
 const execAsync = promisify(exec);
@@ -93,6 +99,9 @@ export function createCreateHandler() {
         return;
       }
 
+      // Ensure the repository has at least one commit so worktree commands referencing HEAD succeed
+      await ensureInitialCommit(projectPath);
+
       // First, check if git already has a worktree for this branch (anywhere)
       const existingWorktree = await findExistingWorktreeForBranch(projectPath, branchName);
       if (existingWorktree) {
diff --git a/apps/server/tests/integration/routes/worktree/create.integration.test.ts b/apps/server/tests/integration/routes/worktree/create.integration.test.ts
new file mode 100644
index 00000000..03b85e7e
--- /dev/null
+++ b/apps/server/tests/integration/routes/worktree/create.integration.test.ts
@@ -0,0 +1,69 @@
+import { describe, it, expect, vi, afterEach } from "vitest";
+import { createCreateHandler } from "@/routes/worktree/routes/create.js";
+import { AUTOMAKER_INITIAL_COMMIT_MESSAGE } from "@/routes/worktree/common.js";
+import { exec } from "child_process";
+import { promisify } from "util";
+import * as fs from "fs/promises";
+import * as os from "os";
+import * as path from "path";
+
+const execAsync = promisify(exec);
+
+describe("worktree create route - repositories without commits", () => {
+  let repoPath: string | null = null;
+
+  async function initRepoWithoutCommit() {
+    repoPath = await fs.mkdtemp(
+      path.join(os.tmpdir(), "automaker-no-commit-")
+    );
+    await execAsync("git init", { cwd: repoPath });
+    await execAsync('git config user.email "test@example.com"', {
+      cwd: repoPath,
+    });
+    await execAsync('git config user.name "Test User"', { cwd: repoPath });
+    // Intentionally skip creating an initial commit
+  }
+
+  afterEach(async () => {
+    if (!repoPath) {
+      return;
+    }
+    await fs.rm(repoPath, { recursive: true, force: true });
+    repoPath = null;
+  });
+
+  it("creates an initial commit before adding a worktree when HEAD is missing", async () => {
+    await initRepoWithoutCommit();
+    const handler = createCreateHandler();
+
+    const json = vi.fn();
+    const status = vi.fn().mockReturnThis();
+    const req = {
+      body: { projectPath: repoPath, branchName: "feature/no-head" },
+    } as any;
+    const res = {
+      json,
+      status,
+    } as any;
+
+    await handler(req, res);
+
+    expect(status).not.toHaveBeenCalled();
+    expect(json).toHaveBeenCalled();
+    const payload = json.mock.calls[0][0];
+    expect(payload.success).toBe(true);
+
+    const { stdout: commitCount } = await execAsync(
+      "git rev-list --count HEAD",
+      { cwd: repoPath! }
+    );
+    expect(Number(commitCount.trim())).toBeGreaterThan(0);
+
+    const { stdout: latestMessage } = await execAsync(
+      "git log -1 --pretty=%B",
+      { cwd: repoPath! }
+    );
+    expect(latestMessage.trim()).toBe(AUTOMAKER_INITIAL_COMMIT_MESSAGE);
+  });
+});
+