diff --git a/packages/server/src/utils/checkout-git.test.ts b/packages/server/src/utils/checkout-git.test.ts
index a5a8db146..d8042d29b 100644
--- a/packages/server/src/utils/checkout-git.test.ts
+++ b/packages/server/src/utils/checkout-git.test.ts
@@ -493,6 +493,53 @@ const x = 1;
     expect(status.aheadOfOrigin).toBeNull();
   });
 
+  it("does not report full history as unpushed for fresh no-track Paseo worktrees", async () => {
+    setupRemoteTrackingMain(repoDir, tempDir);
+    commitFile(repoDir, "second.txt", "second\n", "second commit");
+    execFileSync("git", ["push"], { cwd: repoDir });
+
+    const worktree = await createLegacyWorktreeForTest({
+      branchName: "fresh-feature",
+      cwd: repoDir,
+      baseBranch: "main",
+      worktreeSlug: "fresh-feature",
+      paseoHome,
+    });
+
+    const status = await getCheckoutStatus(worktree.worktreePath, { paseoHome });
+    expect(status).toMatchObject({
+      isGit: true,
+      isPaseoOwnedWorktree: true,
+      baseRef: "main",
+      aheadBehind: { ahead: 0, behind: 0 },
+      aheadOfOrigin: 0,
+    });
+  });
+
+  it("reports local-only worktree commits as unpushed relative to base", async () => {
+    setupRemoteTrackingMain(repoDir, tempDir);
+    commitFile(repoDir, "second.txt", "second\n", "second commit");
+    execFileSync("git", ["push"], { cwd: repoDir });
+
+    const worktree = await createLegacyWorktreeForTest({
+      branchName: "fresh-feature",
+      cwd: repoDir,
+      baseBranch: "main",
+      worktreeSlug: "fresh-feature",
+      paseoHome,
+    });
+    commitFile(worktree.worktreePath, "feature.txt", "feature\n", "feature commit");
+
+    const status = await getCheckoutStatus(worktree.worktreePath, { paseoHome });
+    expect(status).toMatchObject({
+      isGit: true,
+      isPaseoOwnedWorktree: true,
+      baseRef: "main",
+      aheadBehind: { ahead: 1, behind: 0 },
+      aheadOfOrigin: 1,
+    });
+  });
+
   it("does not report incoming additions when the base branch is behind its remote", async () => {
     const { cloneDir } = setupRemoteTrackingMain(repoDir, tempDir);
     commitFile(cloneDir, "file.txt", "remote one\nremote two\n", "remote update");
diff --git a/packages/server/src/utils/checkout-git.ts b/packages/server/src/utils/checkout-git.ts
index ba928da3d..4e4dee915 100644
--- a/packages/server/src/utils/checkout-git.ts
+++ b/packages/server/src/utils/checkout-git.ts
@@ -1268,6 +1268,7 @@ async function getAheadBehind(
 async function getAheadOfOrigin(
   cwd: string,
   currentBranch: string,
+  baseRef: string | null,
   context?: CheckoutContext,
 ): Promise<number | null> {
   if (!currentBranch) {
@@ -1286,12 +1287,15 @@ async function getAheadOfOrigin(
     if (trackedOriginBranch) {
       return null;
     }
+    if (!baseRef || normalizeLocalBranchRefName(baseRef) === currentBranch) {
+      return null;
+    }
     try {
-      const { stdout } = await runGitCommand(["rev-list", "--count", currentBranch], {
-        cwd,
-        envOverlay: READ_ONLY_GIT_ENV,
-        logger: context?.logger,
-      });
+      const comparisonBaseRef = await resolveBestComparisonBaseRef(cwd, baseRef, context);
+      const { stdout } = await runGitCommand(
+        ["rev-list", "--count", `${comparisonBaseRef}..${currentBranch}`],
+        { cwd, envOverlay: READ_ONLY_GIT_ENV, logger: context?.logger },
+      );
       const count = Number.parseInt(stdout.trim(), 10);
       return Number.isNaN(count) ? null : count;
     } catch {
@@ -1503,7 +1507,7 @@ export async function getCheckoutStatus(
       ? getAheadBehind(cwd, baseRef, currentBranch, context)
       : Promise.resolve(null),
     hasRemote && currentBranch
-      ? getAheadOfOrigin(cwd, currentBranch, context)
+      ? getAheadOfOrigin(cwd, currentBranch, baseRef, context)
       : Promise.resolve(null),
     hasRemote && currentBranch
       ? getBehindOfOrigin(cwd, currentBranch, context)