diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index a50f33273..024a3e912 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -2632,7 +2632,12 @@ def _restore_stashed_changes(
             print("Resolve conflicts manually, then run: git stash drop")
 
         print(f"Restore your changes with: git stash apply {stash_ref}")
-        sys.exit(1)
+        # In non-interactive mode (gateway /update), don't abort — the code
+        # update itself succeeded, only the stash restore had conflicts.
+        # Aborting would report the entire update as failed.
+        if prompt_user:
+            sys.exit(1)
+        return False
 
     stash_selector = _resolve_stash_selector(git_cmd, cwd, stash_ref)
     if stash_selector is None:
@@ -2706,30 +2711,60 @@ def cmd_update(args):
 
     # Fetch and pull
     try:
-        print("→ Fetching updates...")
         git_cmd = ["git"]
         if sys.platform == "win32":
             git_cmd = ["git", "-c", "windows.appendAtomically=false"]
-        
-        subprocess.run(git_cmd + ["fetch", "origin"], cwd=PROJECT_ROOT, check=True)
-        
-        # Get current branch
+
+        print("→ Fetching updates...")
+        fetch_result = subprocess.run(
+            git_cmd + ["fetch", "origin"],
+            cwd=PROJECT_ROOT,
+            capture_output=True,
+            text=True,
+        )
+        if fetch_result.returncode != 0:
+            stderr = fetch_result.stderr.strip()
+            if "Could not resolve host" in stderr or "unable to access" in stderr:
+                print("✗ Network error — cannot reach the remote repository.")
+                print(f"  {stderr.splitlines()[0]}" if stderr else "")
+            elif "Authentication failed" in stderr or "could not read Username" in stderr:
+                print("✗ Authentication failed — check your git credentials or SSH key.")
+            else:
+                print(f"✗ Failed to fetch updates from origin.")
+                if stderr:
+                    print(f"  {stderr.splitlines()[0]}")
+            sys.exit(1)
+
+        # Get current branch (returns literal "HEAD" when detached)
         result = subprocess.run(
             git_cmd + ["rev-parse", "--abbrev-ref", "HEAD"],
             cwd=PROJECT_ROOT,
             capture_output=True,
             text=True,
-            check=True
+            check=True,
         )
-        branch = result.stdout.strip()
+        current_branch = result.stdout.strip()
 
-        # Fall back to main if the current branch doesn't exist on the remote
-        verify = subprocess.run(
-            git_cmd + ["rev-parse", "--verify", f"origin/{branch}"],
-            cwd=PROJECT_ROOT, capture_output=True, text=True,
-        )
-        if verify.returncode != 0:
-            branch = "main"
+        # Always update against main
+        branch = "main"
+
+        # If user is on a non-main branch or detached HEAD, switch to main
+        if current_branch != "main":
+            label = "detached HEAD" if current_branch == "HEAD" else f"branch '{current_branch}'"
+            print(f"  ⚠ Currently on {label} — switching to main for update...")
+            # Stash before checkout so uncommitted work isn't lost
+            auto_stash_ref = _stash_local_changes_if_needed(git_cmd, PROJECT_ROOT)
+            subprocess.run(
+                git_cmd + ["checkout", "main"],
+                cwd=PROJECT_ROOT,
+                capture_output=True,
+                text=True,
+                check=True,
+            )
+        else:
+            auto_stash_ref = _stash_local_changes_if_needed(git_cmd, PROJECT_ROOT)
+
+        prompt_for_restore = auto_stash_ref is not None and sys.stdin.isatty() and sys.stdout.isatty()
 
         # Check if there are updates
         result = subprocess.run(
@@ -2737,31 +2772,69 @@ def cmd_update(args):
             cwd=PROJECT_ROOT,
             capture_output=True,
             text=True,
-            check=True
+            check=True,
         )
         commit_count = int(result.stdout.strip())
-        
+
         if commit_count == 0:
             _invalidate_update_cache()
-            print("✓ Already up to date!")
-            return
-        
-        print(f"→ Found {commit_count} new commit(s)")
-
-        auto_stash_ref = _stash_local_changes_if_needed(git_cmd, PROJECT_ROOT)
-        prompt_for_restore = auto_stash_ref is not None and sys.stdin.isatty() and sys.stdout.isatty()
-
-        print("→ Pulling updates...")
-        try:
-            subprocess.run(git_cmd + ["pull", "--ff-only", "origin", branch], cwd=PROJECT_ROOT, check=True)
-        finally:
+            # Restore stash and switch back to original branch if we moved
             if auto_stash_ref is not None:
                 _restore_stashed_changes(
-                    git_cmd,
-                    PROJECT_ROOT,
-                    auto_stash_ref,
+                    git_cmd, PROJECT_ROOT, auto_stash_ref,
                     prompt_user=prompt_for_restore,
                 )
+            if current_branch not in ("main", "HEAD"):
+                subprocess.run(
+                    git_cmd + ["checkout", current_branch],
+                    cwd=PROJECT_ROOT, capture_output=True, text=True, check=False,
+                )
+            print("✓ Already up to date!")
+            return
+
+        print(f"→ Found {commit_count} new commit(s)")
+
+        print("→ Pulling updates...")
+        update_succeeded = False
+        try:
+            pull_result = subprocess.run(
+                git_cmd + ["pull", "--ff-only", "origin", branch],
+                cwd=PROJECT_ROOT,
+                capture_output=True,
+                text=True,
+            )
+            if pull_result.returncode != 0:
+                # ff-only failed — local and remote have diverged (e.g. upstream
+                # force-pushed or rebase).  Since local changes are already
+                # stashed, reset to match the remote exactly.
+                print("  ⚠ Fast-forward not possible (history diverged), resetting to match remote...")
+                reset_result = subprocess.run(
+                    git_cmd + ["reset", "--hard", f"origin/{branch}"],
+                    cwd=PROJECT_ROOT,
+                    capture_output=True,
+                    text=True,
+                )
+                if reset_result.returncode != 0:
+                    print(f"✗ Failed to reset to origin/{branch}.")
+                    if reset_result.stderr.strip():
+                        print(f"  {reset_result.stderr.strip()}")
+                    print("  Try manually: git fetch origin && git reset --hard origin/main")
+                    sys.exit(1)
+            update_succeeded = True
+        finally:
+            if auto_stash_ref is not None:
+                # Don't attempt stash restore if the code update itself failed —
+                # working tree is in an unknown state.
+                if not update_succeeded:
+                    print(f"  ℹ️  Local changes preserved in stash (ref: {auto_stash_ref})")
+                    print(f"  Restore manually with: git stash apply")
+                else:
+                    _restore_stashed_changes(
+                        git_cmd,
+                        PROJECT_ROOT,
+                        auto_stash_ref,
+                        prompt_user=prompt_for_restore,
+                    )
         
         _invalidate_update_cache()
         
diff --git a/tests/hermes_cli/test_update_autostash.py b/tests/hermes_cli/test_update_autostash.py
index 9b8b6d79a..042b4fd47 100644
--- a/tests/hermes_cli/test_update_autostash.py
+++ b/tests/hermes_cli/test_update_autostash.py
@@ -267,7 +267,8 @@ def test_restore_stashed_changes_user_declines_reset(monkeypatch, tmp_path, caps
 
 
 def test_restore_stashed_changes_auto_resets_non_interactive(monkeypatch, tmp_path, capsys):
-    """Non-interactive mode auto-resets without prompting."""
+    """Non-interactive mode auto-resets without prompting and returns False
+    instead of sys.exit(1) so the update can continue (gateway /update path)."""
     calls = []
 
     def fake_run(cmd, **kwargs):
@@ -282,9 +283,9 @@ def test_restore_stashed_changes_auto_resets_non_interactive(monkeypatch, tmp_pa
 
     monkeypatch.setattr(hermes_main.subprocess, "run", fake_run)
 
-    with pytest.raises(SystemExit, match="1"):
-        hermes_main._restore_stashed_changes(["git"], tmp_path, "abc123", prompt_user=False)
+    result = hermes_main._restore_stashed_changes(["git"], tmp_path, "abc123", prompt_user=False)
 
+    assert result is False
     out = capsys.readouterr().out
     assert "Working tree reset to clean state" in out
     reset_calls = [c for c, _ in calls if c[1:3] == ["reset", "--hard"]]
@@ -384,3 +385,236 @@ def test_cmd_update_succeeds_with_extras(monkeypatch, tmp_path):
     install_cmds = [c for c in recorded if "pip" in c and "install" in c]
     assert len(install_cmds) == 1
     assert ".[all]" in install_cmds[0]
+
+
+# ---------------------------------------------------------------------------
+# ff-only fallback to reset --hard on diverged history
+# ---------------------------------------------------------------------------
+
+def _make_update_side_effect(
+    current_branch="main",
+    commit_count="3",
+    ff_only_fails=False,
+    reset_fails=False,
+    fetch_fails=False,
+    fetch_stderr="",
+):
+    """Build a subprocess.run side_effect for cmd_update tests."""
+    recorded = []
+
+    def side_effect(cmd, **kwargs):
+        recorded.append(cmd)
+        joined = " ".join(str(c) for c in cmd)
+        if "fetch" in joined and "origin" in joined:
+            if fetch_fails:
+                return SimpleNamespace(stdout="", stderr=fetch_stderr, returncode=128)
+            return SimpleNamespace(stdout="", stderr="", returncode=0)
+        if "rev-parse" in joined and "--abbrev-ref" in joined:
+            return SimpleNamespace(stdout=f"{current_branch}\n", stderr="", returncode=0)
+        if "checkout" in joined and "main" in joined:
+            return SimpleNamespace(stdout="", stderr="", returncode=0)
+        if "rev-list" in joined:
+            return SimpleNamespace(stdout=f"{commit_count}\n", stderr="", returncode=0)
+        if "--ff-only" in joined:
+            if ff_only_fails:
+                return SimpleNamespace(
+                    stdout="",
+                    stderr="fatal: Not possible to fast-forward, aborting.\n",
+                    returncode=128,
+                )
+            return SimpleNamespace(stdout="Updating abc..def\n", stderr="", returncode=0)
+        if "reset" in joined and "--hard" in joined:
+            if reset_fails:
+                return SimpleNamespace(stdout="", stderr="error: unable to write\n", returncode=1)
+            return SimpleNamespace(stdout="HEAD is now at abc123\n", stderr="", returncode=0)
+        return SimpleNamespace(returncode=0, stdout="", stderr="")
+
+    return side_effect, recorded
+
+
+def test_cmd_update_falls_back_to_reset_when_ff_only_fails(monkeypatch, tmp_path, capsys):
+    """When --ff-only fails (diverged history), update resets to origin/{branch}."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+    monkeypatch.setattr("shutil.which", lambda name: "/usr/bin/uv" if name == "uv" else None)
+
+    side_effect, recorded = _make_update_side_effect(ff_only_fails=True)
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    hermes_main.cmd_update(SimpleNamespace())
+
+    reset_calls = [c for c in recorded if "reset" in c and "--hard" in c]
+    assert len(reset_calls) == 1
+    assert reset_calls[0] == ["git", "reset", "--hard", "origin/main"]
+
+    out = capsys.readouterr().out
+    assert "Fast-forward not possible" in out
+
+
+def test_cmd_update_no_reset_when_ff_only_succeeds(monkeypatch, tmp_path):
+    """When --ff-only succeeds, no reset is attempted."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+    monkeypatch.setattr("shutil.which", lambda name: "/usr/bin/uv" if name == "uv" else None)
+
+    side_effect, recorded = _make_update_side_effect()
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    hermes_main.cmd_update(SimpleNamespace())
+
+    reset_calls = [c for c in recorded if "reset" in c and "--hard" in c]
+    assert len(reset_calls) == 0
+
+
+# ---------------------------------------------------------------------------
+# Non-main branch → auto-checkout main
+# ---------------------------------------------------------------------------
+
+def test_cmd_update_switches_to_main_from_feature_branch(monkeypatch, tmp_path, capsys):
+    """When on a feature branch, update checks out main before pulling."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+    monkeypatch.setattr("shutil.which", lambda name: "/usr/bin/uv" if name == "uv" else None)
+
+    side_effect, recorded = _make_update_side_effect(current_branch="fix/something")
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    hermes_main.cmd_update(SimpleNamespace())
+
+    checkout_calls = [c for c in recorded if "checkout" in c and "main" in c]
+    assert len(checkout_calls) == 1
+
+    out = capsys.readouterr().out
+    assert "fix/something" in out
+    assert "switching to main" in out
+
+
+def test_cmd_update_switches_to_main_from_detached_head(monkeypatch, tmp_path, capsys):
+    """When in detached HEAD state, update checks out main before pulling."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+    monkeypatch.setattr("shutil.which", lambda name: "/usr/bin/uv" if name == "uv" else None)
+
+    side_effect, recorded = _make_update_side_effect(current_branch="HEAD")
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    hermes_main.cmd_update(SimpleNamespace())
+
+    checkout_calls = [c for c in recorded if "checkout" in c and "main" in c]
+    assert len(checkout_calls) == 1
+
+    out = capsys.readouterr().out
+    assert "detached HEAD" in out
+
+
+def test_cmd_update_restores_stash_and_branch_when_already_up_to_date(monkeypatch, tmp_path, capsys):
+    """When on a feature branch with no updates, stash is restored and branch switched back."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+    monkeypatch.setattr("shutil.which", lambda name: "/usr/bin/uv" if name == "uv" else None)
+
+    # Enable stash so it returns a ref
+    monkeypatch.setattr(
+        hermes_main, "_stash_local_changes_if_needed",
+        lambda *a, **kw: "abc123deadbeef",
+    )
+    restore_calls = []
+    monkeypatch.setattr(
+        hermes_main, "_restore_stashed_changes",
+        lambda *a, **kw: restore_calls.append(1) or True,
+    )
+
+    side_effect, recorded = _make_update_side_effect(
+        current_branch="fix/something", commit_count="0",
+    )
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    hermes_main.cmd_update(SimpleNamespace())
+
+    # Stash should have been restored
+    assert len(restore_calls) == 1
+
+    # Should have checked out back to the original branch
+    checkout_back = [c for c in recorded if "checkout" in c and "fix/something" in c]
+    assert len(checkout_back) == 1
+
+    out = capsys.readouterr().out
+    assert "Already up to date" in out
+
+
+def test_cmd_update_no_checkout_when_already_on_main(monkeypatch, tmp_path):
+    """When already on main, no checkout is needed."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+    monkeypatch.setattr("shutil.which", lambda name: "/usr/bin/uv" if name == "uv" else None)
+
+    side_effect, recorded = _make_update_side_effect()
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    hermes_main.cmd_update(SimpleNamespace())
+
+    checkout_calls = [c for c in recorded if "checkout" in c]
+    assert len(checkout_calls) == 0
+
+
+# ---------------------------------------------------------------------------
+# Fetch failure — friendly error messages
+# ---------------------------------------------------------------------------
+
+def test_cmd_update_network_error_shows_friendly_message(monkeypatch, tmp_path, capsys):
+    """Network failures during fetch show a user-friendly message."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+
+    side_effect, _ = _make_update_side_effect(
+        fetch_fails=True,
+        fetch_stderr="fatal: unable to access 'https://...': Could not resolve host: github.com",
+    )
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    with pytest.raises(SystemExit, match="1"):
+        hermes_main.cmd_update(SimpleNamespace())
+
+    out = capsys.readouterr().out
+    assert "Network error" in out
+
+
+def test_cmd_update_auth_error_shows_friendly_message(monkeypatch, tmp_path, capsys):
+    """Auth failures during fetch show a user-friendly message."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+
+    side_effect, _ = _make_update_side_effect(
+        fetch_fails=True,
+        fetch_stderr="fatal: Authentication failed for 'https://...'",
+    )
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    with pytest.raises(SystemExit, match="1"):
+        hermes_main.cmd_update(SimpleNamespace())
+
+    out = capsys.readouterr().out
+    assert "Authentication failed" in out
+
+
+# ---------------------------------------------------------------------------
+# reset --hard failure — don't attempt stash restore
+# ---------------------------------------------------------------------------
+
+def test_cmd_update_skips_stash_restore_when_reset_fails(monkeypatch, tmp_path, capsys):
+    """When reset --hard fails, stash restore is skipped with a helpful message."""
+    _setup_update_mocks(monkeypatch, tmp_path)
+    # Re-enable stash so it actually returns a ref
+    monkeypatch.setattr(
+        hermes_main, "_stash_local_changes_if_needed",
+        lambda *a, **kw: "abc123deadbeef",
+    )
+    restore_calls = []
+    monkeypatch.setattr(
+        hermes_main, "_restore_stashed_changes",
+        lambda *a, **kw: restore_calls.append(1) or True,
+    )
+
+    side_effect, _ = _make_update_side_effect(ff_only_fails=True, reset_fails=True)
+    monkeypatch.setattr(hermes_main.subprocess, "run", side_effect)
+
+    with pytest.raises(SystemExit, match="1"):
+        hermes_main.cmd_update(SimpleNamespace())
+
+    # Stash restore should NOT have been called
+    assert len(restore_calls) == 0
+
+    out = capsys.readouterr().out
+    assert "preserved in stash" in out