diff --git a/src/specify_cli/workflows/_commands.py b/src/specify_cli/workflows/_commands.py
index c517bc620..691fa8945 100644
--- a/src/specify_cli/workflows/_commands.py
+++ b/src/specify_cli/workflows/_commands.py
@@ -374,7 +374,7 @@ def workflow_run(
 
     if registered_id is not None:
         installed_meta = WorkflowRegistry(project_root).get(registered_id)
-        if isinstance(installed_meta, dict) and installed_meta.get("enabled", True) is False:
+        if isinstance(installed_meta, dict) and not installed_meta.get("enabled", True):
             err.print(
                 f"[red]Error:[/red] Workflow '{_escape_markup(registered_id)}' is disabled. "
                 f"Enable with: specify workflow enable {_escape_markup(registered_id)}"
@@ -983,7 +983,7 @@ def _install_workflow_from_catalog(
     }
     # Preserve a prior disabled state across updates/reinstalls.
     existing = registry.get(workflow_id)
-    if isinstance(existing, dict) and existing.get("enabled", True) is False:
+    if isinstance(existing, dict) and not existing.get("enabled", True):
         entry["enabled"] = False
     registry.add(workflow_id, entry)
     console.print(
@@ -1085,6 +1085,7 @@ def workflow_update(
     console.print("🔄 Checking for updates...\n")
 
     updates_available: list[dict[str, str]] = []
+    checked = 0
     for wf_id in targets:
         safe_id = _escape_markup(str(wf_id))
         metadata = installed.get(wf_id)
@@ -1122,14 +1123,19 @@ def workflow_update(
             )
             continue
         if catalog_version > installed_version:
+            checked += 1
             updates_available.append(
                 {"id": wf_id, "installed": str(installed_version), "available": str(catalog_version)}
             )
         else:
+            checked += 1
             console.print(f"✓ {safe_id}: Up to date (v{installed_version})")
 
     if not updates_available:
-        console.print("\n[green]All workflows are up to date![/green]")
+        if checked:
+            console.print("\n[green]All workflows are up to date![/green]")
+        else:
+            console.print("\n[yellow]No workflows were eligible for update[/yellow]")
         raise typer.Exit(0)
 
     console.print("\n[bold]Updates available:[/bold]\n")
diff --git a/src/specify_cli/workflows/catalog.py b/src/specify_cli/workflows/catalog.py
index d8855a06a..203fb6753 100644
--- a/src/specify_cli/workflows/catalog.py
+++ b/src/specify_cli/workflows/catalog.py
@@ -93,12 +93,22 @@ class WorkflowRegistry:
         from datetime import datetime, timezone
 
         existing = self.data["workflows"].get(workflow_id, {})
+        had_entry = workflow_id in self.data["workflows"]
         metadata["installed_at"] = existing.get(
             "installed_at", datetime.now(timezone.utc).isoformat()
         )
         metadata["updated_at"] = datetime.now(timezone.utc).isoformat()
         self.data["workflows"][workflow_id] = metadata
-        self.save()
+        try:
+            self.save()
+        except OSError:
+            # Roll back the in-memory mutation so a later successful save
+            # cannot persist metadata for a write that failed.
+            if had_entry:
+                self.data["workflows"][workflow_id] = existing
+            else:
+                del self.data["workflows"][workflow_id]
+            raise
 
     def remove(self, workflow_id: str) -> bool:
         """Remove an installed workflow entry. Returns True if found."""
diff --git a/tests/test_workflows.py b/tests/test_workflows.py
index 7554deb0d..083e2638e 100644
--- a/tests/test_workflows.py
+++ b/tests/test_workflows.py
@@ -7533,6 +7533,47 @@ steps:
         result = runner.invoke(app, ["workflow", "update"])
         assert result.exit_code == 0, result.output
         assert "re-add to update" in result.output
+        # Every target was skipped — must not claim everything is up to date.
+        assert "No workflows were eligible for update" in result.output
+        assert "up to date!" not in result.output
+
+    def test_registry_add_rolls_back_memory_on_save_failure(self, project_dir, monkeypatch):
+        from specify_cli.workflows.catalog import WorkflowRegistry
+
+        registry = WorkflowRegistry(project_dir)
+        registry.add("align-wf", {"version": "1.0.0", "source": "catalog"})
+
+        def boom():
+            raise OSError("disk full")
+
+        monkeypatch.setattr(registry, "save", boom)
+        with pytest.raises(OSError):
+            registry.add("align-wf", {"version": "2.0.0", "source": "catalog"})
+        assert registry.get("align-wf")["version"] == "1.0.0"
+
+        with pytest.raises(OSError):
+            registry.add("other-wf", {"version": "1.0.0", "source": "catalog"})
+        assert registry.get("other-wf") is None
+
+    def test_run_refuses_falsy_non_bool_enabled(self, project_dir, monkeypatch):
+        """"enabled": 0 shows as disabled in list — run must agree."""
+        import json as json_mod
+
+        from typer.testing import CliRunner
+        from specify_cli import app
+        from specify_cli.workflows.catalog import WorkflowRegistry
+
+        monkeypatch.chdir(project_dir)
+        runner = CliRunner()
+        self._install_dev(runner, app, project_dir)
+
+        registry = WorkflowRegistry(project_dir)
+        registry.data["workflows"]["align-wf"]["enabled"] = 0
+        registry.registry_path.write_text(json_mod.dumps(registry.data), encoding="utf-8")
+
+        result = runner.invoke(app, ["workflow", "run", "align-wf"])
+        assert result.exit_code != 0
+        assert "disabled" in result.output
 
     def test_update_installs_newer_catalog_version(self, project_dir, monkeypatch):
         from unittest.mock import patch