diff --git a/test/dashbot/services/url_env_service_test.dart b/test/dashbot/services/url_env_service_test.dart
index 7f776eb1..237851b5 100644
--- a/test/dashbot/services/url_env_service_test.dart
+++ b/test/dashbot/services/url_env_service_test.dart
@@ -13,21 +13,46 @@ void main() {
       expect(svc.inferBaseUrl('http://localhost:8080/api'),
           'http://localhost:8080');
     });
+    test('with port 0 (default port)', () {
+      expect(svc.inferBaseUrl('https://api.apidash.dev:0/api'),
+          'https://api.apidash.dev');
+    });
+    test('without port (hasPort false)', () {
+      expect(svc.inferBaseUrl('https://api.apidash.dev/api'),
+          'https://api.apidash.dev');
+    });
+    test('url without scheme', () {
+      expect(svc.inferBaseUrl('api.apidash.dev/path'), '');
+    });
+    test('url without host', () {
+      expect(svc.inferBaseUrl('https:///path'), '');
+    });
+    test('fallback regex match', () {
+      // This will hit the regex fallback path since Uri.parse will fail
+      // to extract proper scheme/host for malformed URLs but regex can still match
+      expect(svc.inferBaseUrl('https://malformed..host/path'),
+          'https://malformed..host');
+    });
     test('invalid returns empty', () {
       expect(svc.inferBaseUrl('not a url'), '');
     });
+    test('regex fallback with valid http url', () {
+      // Create a scenario where Uri.parse succeeds but doesn't have proper host
+      expect(svc.inferBaseUrl('file://localhost/path'), 'file://localhost');
+    });
   });
 
   group('UrlEnvService.ensureBaseUrlEnv & maybeSubstituteBaseUrl', () {
     final svc = UrlEnvService();
-    final envId = 'env1';
-    final envs = <String, EnvironmentModel>{
-      envId: const EnvironmentModel(id: 'env1', name: 'Env1', values: []),
-    };
-    String? activeId = envId;
-    EnvironmentModel? updated;
 
     test('ensure adds variable if missing and returns key', () async {
+      final envId = 'env1';
+      final envs = <String, EnvironmentModel>{
+        envId: const EnvironmentModel(id: 'env1', name: 'Env1', values: []),
+      };
+      String? activeId = envId;
+      EnvironmentModel? updated;
+
       final key = await svc.ensureBaseUrlEnv(
         'https://api.apidash.dev',
         readEnvs: () => envs,
@@ -41,16 +66,114 @@ void main() {
       expect(updated!.values.any((v) => v.key == key), true);
     });
 
-    test('maybeSubstituteBaseUrl replaces prefix with variable', () async {
+    test('empty baseUrl returns BASE_URL', () async {
+      final key = await svc.ensureBaseUrlEnv(
+        '',
+        readEnvs: () => <String, EnvironmentModel>{},
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {},
+      );
+      expect(key, 'BASE_URL');
+    });
+
+    test('uses global environment when activeId is null', () async {
+      final envs = <String, EnvironmentModel>{
+        'global':
+            const EnvironmentModel(id: 'global', name: 'Global', values: []),
+      };
+      EnvironmentModel? updated;
+
       final key = await svc.ensureBaseUrlEnv(
         'https://api.apidash.dev',
         readEnvs: () => envs,
+        readActiveEnvId: () => null, // This should default to global
+        updateEnv: (id, {values}) {
+          updated = envs[id]!.copyWith(values: values ?? const []);
+          envs[id] = updated!;
+        },
+      );
+      expect(key, 'BASE_URL_API_APIDASH_DEV');
+      expect(updated!.values.any((v) => v.key == key), true);
+    });
+
+    test('does not add variable if it already exists', () async {
+      final envId = 'env1';
+      final existingVar = EnvironmentVariableModel(
+        key: 'BASE_URL_API_APIDASH_DEV',
+        value: 'https://existing.com',
+        enabled: true,
+      );
+      final envs = <String, EnvironmentModel>{
+        envId:
+            EnvironmentModel(id: 'env1', name: 'Env1', values: [existingVar]),
+      };
+      String? activeId = envId;
+      bool updateCalled = false;
+
+      final key = await svc.ensureBaseUrlEnv(
+        'https://api.apidash.dev',
+        readEnvs: () => envs,
+        readActiveEnvId: () => activeId,
+        updateEnv: (id, {values}) {
+          updateCalled = true;
+        },
+      );
+      expect(key, 'BASE_URL_API_APIDASH_DEV');
+      expect(
+          updateCalled, false); // Should not call update since variable exists
+    });
+
+    test('handles null envs', () async {
+      final key = await svc.ensureBaseUrlEnv(
+        'https://api.apidash.dev',
+        readEnvs: () => null,
+        readActiveEnvId: () => 'env1',
+        updateEnv: (id, {values}) {},
+      );
+      expect(key, 'BASE_URL_API_APIDASH_DEV');
+    });
+
+    test('handles null envModel', () async {
+      final envs = <String, EnvironmentModel>{};
+      final key = await svc.ensureBaseUrlEnv(
+        'https://api.apidash.dev',
+        readEnvs: () => envs,
+        readActiveEnvId: () => 'nonexistent',
+        updateEnv: (id, {values}) {},
+      );
+      expect(key, 'BASE_URL_API_APIDASH_DEV');
+    });
+
+    test('handles malformed URL in ensureBaseUrlEnv', () async {
+      final envId = 'env1';
+      final envs = <String, EnvironmentModel>{
+        envId: const EnvironmentModel(id: 'env1', name: 'Env1', values: []),
+      };
+      String? activeId = envId;
+      EnvironmentModel? updated;
+
+      final key = await svc.ensureBaseUrlEnv(
+        'not-a-valid-url',
+        readEnvs: () => envs,
         readActiveEnvId: () => activeId,
         updateEnv: (id, {values}) {
           updated = envs[id]!.copyWith(values: values ?? const []);
           envs[id] = updated!;
         },
       );
+      expect(key, 'BASE_URL_API'); // Should fallback to 'API'
+      expect(updated!.values.any((v) => v.key == key), true);
+    });
+
+    test('maybeSubstituteBaseUrl replaces prefix with variable', () async {
+      final key = await svc.ensureBaseUrlEnv(
+        'https://api.apidash.dev',
+        readEnvs: () => <String, EnvironmentModel>{
+          'env1': const EnvironmentModel(id: 'env1', name: 'Env1', values: []),
+        },
+        readActiveEnvId: () => 'env1',
+        updateEnv: (id, {values}) {},
+      );
       final replaced = await svc.maybeSubstituteBaseUrl(
         'https://api.apidash.dev/v1/users',
         'https://api.apidash.dev',
@@ -58,5 +181,399 @@ void main() {
       );
       expect(replaced, '{{$key}}/v1/users');
     });
+
+    test('maybeSubstituteBaseUrl returns original URL when baseUrl is empty',
+        () async {
+      final url = 'https://api.apidash.dev/v1/users';
+      final result = await svc.maybeSubstituteBaseUrl(
+        url,
+        '',
+        ensure: (_) async => 'BASE_URL_API',
+      );
+      expect(result, url);
+    });
+
+    test(
+        'maybeSubstituteBaseUrl returns original URL when URL does not start with baseUrl',
+        () async {
+      final url = 'https://different.com/v1/users';
+      final baseUrl = 'https://api.apidash.dev';
+      final result = await svc.maybeSubstituteBaseUrl(
+        url,
+        baseUrl,
+        ensure: (_) async => 'BASE_URL_API',
+      );
+      expect(result, url);
+    });
+
+    test('maybeSubstituteBaseUrl handles path without leading slash', () async {
+      final result = await svc.maybeSubstituteBaseUrl(
+        'https://api.apidash.devv1/users', // No slash between baseUrl and path
+        'https://api.apidash.dev',
+        ensure: (_) async => 'BASE_URL_API',
+      );
+      expect(result, '{{BASE_URL_API}}/v1/users');
+    });
+
+    test('maybeSubstituteBaseUrl handles exact baseUrl match', () async {
+      final result = await svc.maybeSubstituteBaseUrl(
+        'https://api.apidash.dev',
+        'https://api.apidash.dev',
+        ensure: (_) async => 'BASE_URL_API',
+      );
+      expect(result, '{{BASE_URL_API}}/');
+    });
+  });
+
+  group('UrlEnvService.ensureBaseUrlEnvForOpenApi', () {
+    final svc = UrlEnvService();
+
+    test('handles empty baseUrl with title', () async {
+      final envs = <String, EnvironmentModel>{
+        'global':
+            const EnvironmentModel(id: 'global', name: 'Global', values: []),
+      };
+      EnvironmentModel? updated;
+
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: 'Pet Store API',
+        readEnvs: () => envs,
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {
+          updated = envs[id]!.copyWith(values: values ?? const []);
+          envs[id] = updated!;
+        },
+      );
+
+      expect(key, 'BASE_URL_PET');
+      expect(updated!.values.any((v) => v.key == key), true);
+      final createdVar = updated!.values.firstWhere((v) => v.key == key);
+      expect(
+          createdVar.value, ''); // Empty baseUrl should result in empty value
+    });
+
+    test('handles "/" baseUrl with title', () async {
+      final envs = <String, EnvironmentModel>{
+        'global':
+            const EnvironmentModel(id: 'global', name: 'Global', values: []),
+      };
+      EnvironmentModel? updated;
+
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '/',
+        title: 'Pet Store API',
+        readEnvs: () => envs,
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {
+          updated = envs[id]!.copyWith(values: values ?? const []);
+          envs[id] = updated!;
+        },
+      );
+
+      expect(key, 'BASE_URL_PET');
+      expect(updated!.values.any((v) => v.key == key), true);
+      final createdVar = updated!.values.firstWhere((v) => v.key == key);
+      expect(createdVar.value, ''); // "/" should result in empty value
+    });
+
+    test('handles path-only baseUrl (no scheme) with title', () async {
+      final envs = <String, EnvironmentModel>{
+        'global':
+            const EnvironmentModel(id: 'global', name: 'Global', values: []),
+      };
+      EnvironmentModel? updated;
+
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '/api/v1',
+        title: 'Pet Store API',
+        readEnvs: () => envs,
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {
+          updated = envs[id]!.copyWith(values: values ?? const []);
+          envs[id] = updated!;
+        },
+      );
+
+      expect(key, 'BASE_URL_PET');
+      expect(updated!.values.any((v) => v.key == key), true);
+      final createdVar = updated!.values.firstWhere((v) => v.key == key);
+      expect(createdVar.value, '/api/v1');
+    });
+
+    test('handles variable server URL with title', () async {
+      final envs = <String, EnvironmentModel>{
+        'global':
+            const EnvironmentModel(id: 'global', name: 'Global', values: []),
+      };
+      EnvironmentModel? updated;
+
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '{server}/api',
+        title: 'Pet Store API',
+        readEnvs: () => envs,
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {
+          updated = envs[id]!.copyWith(values: values ?? const []);
+          envs[id] = updated!;
+        },
+      );
+
+      expect(key, 'BASE_URL_PET');
+      expect(updated!.values.any((v) => v.key == key), true);
+      final createdVar = updated!.values.firstWhere((v) => v.key == key);
+      expect(createdVar.value, '{server}/api');
+    });
+
+    test('handles full URL with host extraction', () async {
+      final envs = <String, EnvironmentModel>{
+        'global':
+            const EnvironmentModel(id: 'global', name: 'Global', values: []),
+      };
+      EnvironmentModel? updated;
+
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        'https://petstore.swagger.io/v2',
+        title: 'Pet Store API',
+        readEnvs: () => envs,
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {
+          updated = envs[id]!.copyWith(values: values ?? const []);
+          envs[id] = updated!;
+        },
+      );
+
+      expect(key, 'BASE_URL_PETSTORE_SWAGGER_IO'); // Should use full host
+      expect(updated!.values.any((v) => v.key == key), true);
+      final createdVar = updated!.values.firstWhere((v) => v.key == key);
+      expect(createdVar.value, 'https://petstore.swagger.io/v2');
+    });
+
+    test('handles malformed URL with title fallback', () async {
+      final envs = <String, EnvironmentModel>{
+        'global':
+            const EnvironmentModel(id: 'global', name: 'Global', values: []),
+      };
+      EnvironmentModel? updated;
+
+      // Use a URL that will fail to parse but is not considered trivial
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        'not-http-or-https://invalid',
+        title: 'My Orders Service',
+        readEnvs: () => envs,
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {
+          updated = envs[id]!.copyWith(values: values ?? const []);
+          envs[id] = updated!;
+        },
+      );
+
+      // The URL "not-http-or-https://invalid" will parse and extract "invalid" as host
+      expect(key, 'BASE_URL_INVALID');
+      expect(updated!.values.any((v) => v.key == key), true);
+    });
+
+    test('does not add variable if it already exists (trivial case)', () async {
+      final existingVar = EnvironmentVariableModel(
+        key: 'BASE_URL_PET',
+        value: 'existing value',
+        enabled: true,
+      );
+      final envs = <String, EnvironmentModel>{
+        'global': EnvironmentModel(
+            id: 'global', name: 'Global', values: [existingVar]),
+      };
+      bool updateCalled = false;
+
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: 'Pet Store API',
+        readEnvs: () => envs,
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {
+          updateCalled = true;
+        },
+      );
+
+      expect(key, 'BASE_URL_PET');
+      expect(updateCalled, false); // Should not update since variable exists
+    });
+
+    test('does not add variable if it already exists (full URL case)',
+        () async {
+      final existingVar = EnvironmentVariableModel(
+        key: 'BASE_URL_PETSTORE_SWAGGER_IO',
+        value: 'existing value',
+        enabled: true,
+      );
+      final envs = <String, EnvironmentModel>{
+        'global': EnvironmentModel(
+            id: 'global', name: 'Global', values: [existingVar]),
+      };
+      bool updateCalled = false;
+
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        'https://petstore.swagger.io/v2',
+        title: 'Pet Store API',
+        readEnvs: () => envs,
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {
+          updateCalled = true;
+        },
+      );
+
+      expect(key, 'BASE_URL_PETSTORE_SWAGGER_IO');
+      expect(updateCalled, false);
+    });
+
+    test('handles null envModel (trivial case)', () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: 'Pet Store API',
+        readEnvs: () => <String, EnvironmentModel>{},
+        readActiveEnvId: () => 'nonexistent',
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key, 'BASE_URL_PET');
+    });
+
+    test('handles null envModel (full URL case)', () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        'https://petstore.swagger.io/v2',
+        title: 'Pet Store API',
+        readEnvs: () => <String, EnvironmentModel>{},
+        readActiveEnvId: () => 'nonexistent',
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key, 'BASE_URL_PETSTORE_SWAGGER_IO');
+    });
+
+    test('handles null envs', () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        'https://petstore.swagger.io/v2',
+        title: 'Pet Store API',
+        readEnvs: () => null,
+        readActiveEnvId: () => 'env1',
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key, 'BASE_URL_PETSTORE_SWAGGER_IO');
+    });
+  });
+
+  group('UrlEnvService._slugFromOpenApiTitleFirstWord', () {
+    final svc = UrlEnvService();
+
+    test('extracts first word from simple title', () {
+      // We can't test private method directly, but we can test it through ensureBaseUrlEnvForOpenApi
+      final result = svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: 'Pet Store API',
+        readEnvs: () => <String, EnvironmentModel>{
+          'global':
+              const EnvironmentModel(id: 'global', name: 'Global', values: []),
+        },
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {},
+      );
+
+      result.then((key) => expect(key, 'BASE_URL_PET'));
+    });
+
+    test('handles title with special characters', () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: 'My-Orders Service',
+        readEnvs: () => <String, EnvironmentModel>{
+          'global':
+              const EnvironmentModel(id: 'global', name: 'Global', values: []),
+        },
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key,
+          'BASE_URL_MY_ORDERS'); // First word "My-Orders" -> "MY_ORDERS" (hyphens become underscores)
+    });
+
+    test('handles empty title', () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: '',
+        readEnvs: () => <String, EnvironmentModel>{
+          'global':
+              const EnvironmentModel(id: 'global', name: 'Global', values: []),
+        },
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key, 'BASE_URL_API'); // Should fallback to API
+    });
+
+    test('handles whitespace-only title', () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: '   \t\n  ',
+        readEnvs: () => <String, EnvironmentModel>{
+          'global':
+              const EnvironmentModel(id: 'global', name: 'Global', values: []),
+        },
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key, 'BASE_URL_API');
+    });
+
+    test('handles title with only special characters', () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: '--- ### !!!',
+        readEnvs: () => <String, EnvironmentModel>{
+          'global':
+              const EnvironmentModel(id: 'global', name: 'Global', values: []),
+        },
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key, 'BASE_URL_API');
+    });
+
+    test('handles title with leading/trailing underscores after cleaning',
+        () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: '__Test___API__',
+        readEnvs: () => <String, EnvironmentModel>{
+          'global':
+              const EnvironmentModel(id: 'global', name: 'Global', values: []),
+        },
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key,
+          'BASE_URL_TEST_API'); // First word "__Test___API__" -> "TEST_API" (cleaned)
+    });
+
+    test('handles multiple consecutive underscores', () async {
+      final key = await svc.ensureBaseUrlEnvForOpenApi(
+        '',
+        title: 'Test___Multiple___Underscores',
+        readEnvs: () => <String, EnvironmentModel>{
+          'global':
+              const EnvironmentModel(id: 'global', name: 'Global', values: []),
+        },
+        readActiveEnvId: () => null,
+        updateEnv: (id, {values}) {},
+      );
+
+      expect(key,
+          'BASE_URL_TEST_MULTIPLE_UNDERSCORES'); // First word "Test___Multiple___Underscores" -> "TEST_MULTIPLE_UNDERSCORES"
+    });
   });
 }