diff --git a/packages/twenty-sdk/src/cli/utilities/version/__tests__/get-server-version-from-api.test.ts b/packages/twenty-sdk/src/cli/utilities/version/__tests__/get-server-version-from-api.test.ts
new file mode 100644
index 0000000000..ab312d0c37
--- /dev/null
+++ b/packages/twenty-sdk/src/cli/utilities/version/__tests__/get-server-version-from-api.test.ts
@@ -0,0 +1,108 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest';
+
+import { getServerVersionFromApi } from '@/cli/utilities/version/get-server-version-from-api';
+
+const { mockedGetConfig } = vi.hoisted(() => ({
+  mockedGetConfig: vi.fn(),
+}));
+
+vi.mock('@/cli/utilities/config/config-service', () => ({
+  ConfigService: class {
+    getConfig = mockedGetConfig;
+  },
+}));
+
+const mockFetch = (
+  impl: (
+    input: string,
+  ) => Promise<{ ok: boolean; json: () => Promise<unknown> }>,
+) => {
+  global.fetch = vi.fn(impl as unknown as typeof fetch);
+};
+
+describe('getServerVersionFromApi', () => {
+  const originalFetch = global.fetch;
+
+  beforeEach(() => {
+    vi.clearAllMocks();
+    mockedGetConfig.mockResolvedValue({ apiUrl: 'http://localhost:2020' });
+  });
+
+  afterEach(() => {
+    vi.restoreAllMocks();
+    global.fetch = originalFetch;
+  });
+
+  it('returns the version reported by the server card endpoint', async () => {
+    mockFetch(async () => ({
+      ok: true,
+      json: async () => ({ version: '2.16.1' }),
+    }));
+
+    expect(await getServerVersionFromApi()).toBe('2.16.1');
+    expect(global.fetch).toHaveBeenCalledWith(
+      'http://localhost:2020/.well-known/mcp/server-card.json',
+      expect.anything(),
+    );
+  });
+
+  it('uses the provided apiUrl over the config, stripping a trailing slash', async () => {
+    mockFetch(async () => ({
+      ok: true,
+      json: async () => ({ version: 'v2.19.0' }),
+    }));
+
+    expect(await getServerVersionFromApi('http://example.com/')).toBe('2.19.0');
+    expect(mockedGetConfig).not.toHaveBeenCalled();
+    expect(global.fetch).toHaveBeenCalledWith(
+      'http://example.com/.well-known/mcp/server-card.json',
+      expect.anything(),
+    );
+  });
+
+  it('returns null for the 0.0.0 fallback version', async () => {
+    mockFetch(async () => ({
+      ok: true,
+      json: async () => ({ version: '0.0.0' }),
+    }));
+
+    expect(await getServerVersionFromApi()).toBeNull();
+  });
+
+  it('returns null for a non-semver version', async () => {
+    mockFetch(async () => ({
+      ok: true,
+      json: async () => ({ version: 'latest' }),
+    }));
+
+    expect(await getServerVersionFromApi()).toBeNull();
+  });
+
+  it('returns null when the version field is missing', async () => {
+    mockFetch(async () => ({ ok: true, json: async () => ({}) }));
+
+    expect(await getServerVersionFromApi()).toBeNull();
+  });
+
+  it('returns null on a non-ok response', async () => {
+    mockFetch(async () => ({ ok: false, json: async () => ({}) }));
+
+    expect(await getServerVersionFromApi()).toBeNull();
+  });
+
+  it('returns null when the request throws', async () => {
+    global.fetch = vi.fn(async () => {
+      throw new Error('network error');
+    }) as unknown as typeof fetch;
+
+    expect(await getServerVersionFromApi()).toBeNull();
+  });
+
+  it('returns null when no apiUrl is configured', async () => {
+    mockedGetConfig.mockResolvedValue({ apiUrl: '' });
+    global.fetch = vi.fn() as unknown as typeof fetch;
+
+    expect(await getServerVersionFromApi()).toBeNull();
+    expect(global.fetch).not.toHaveBeenCalled();
+  });
+});
diff --git a/packages/twenty-sdk/src/cli/utilities/version/get-server-version-from-api.ts b/packages/twenty-sdk/src/cli/utilities/version/get-server-version-from-api.ts
new file mode 100644
index 0000000000..2e1ef3e41d
--- /dev/null
+++ b/packages/twenty-sdk/src/cli/utilities/version/get-server-version-from-api.ts
@@ -0,0 +1,47 @@
+import { ConfigService } from '@/cli/utilities/config/config-service';
+import { parseSemver } from '@/cli/utilities/version/parse-semver';
+
+const SERVER_CARD_PATH = '/.well-known/mcp/server-card.json';
+const FETCH_TIMEOUT_MS = 3000;
+
+export const getServerVersionFromApi = async (
+  apiUrl?: string,
+): Promise<string | null> => {
+  const baseUrl = apiUrl ?? (await new ConfigService().getConfig()).apiUrl;
+
+  if (!baseUrl) {
+    return null;
+  }
+
+  const controller = new AbortController();
+  const timeoutId = setTimeout(() => controller.abort(), FETCH_TIMEOUT_MS);
+
+  try {
+    const response = await fetch(
+      `${baseUrl.replace(/\/$/, '')}${SERVER_CARD_PATH}`,
+      { signal: controller.signal },
+    );
+
+    if (!response.ok) {
+      return null;
+    }
+
+    const body = (await response.json()) as { version?: unknown };
+
+    if (typeof body.version !== 'string') {
+      return null;
+    }
+
+    const version = body.version.trim().replace(/^v/, '');
+
+    if (version === '0.0.0' || parseSemver(version) === null) {
+      return null;
+    }
+
+    return version;
+  } catch {
+    return null;
+  } finally {
+    clearTimeout(timeoutId);
+  }
+};
diff --git a/packages/twenty-sdk/src/cli/utilities/version/get-version-info.ts b/packages/twenty-sdk/src/cli/utilities/version/get-version-info.ts
index 24d485a737..5a11bc7039 100644
--- a/packages/twenty-sdk/src/cli/utilities/version/get-version-info.ts
+++ b/packages/twenty-sdk/src/cli/utilities/version/get-version-info.ts
@@ -1,11 +1,66 @@
-import { CONTAINER_NAME } from '@/cli/utilities/server/docker-container';
+import { ConfigService } from '@/cli/utilities/config/config-service';
+import {
+  CONTAINER_NAME,
+  getContainerPort,
+  isContainerRunning,
+} from '@/cli/utilities/server/docker-container';
 import { compareSemver } from '@/cli/utilities/version/compare-semver';
 import { getLocalServerVersion } from '@/cli/utilities/version/get-local-server-version';
 import { getPublishedServerVersions } from '@/cli/utilities/version/get-published-server-versions';
+import { getServerVersionFromApi } from '@/cli/utilities/version/get-server-version-from-api';
 import { parseSemver } from '@/cli/utilities/version/parse-semver';
 import { type VersionInfo } from '@/cli/utilities/version/version-info';
 import sdkPackageJson from '../../../../package.json';
 
+const LOCAL_REMOTE_NAME = 'local';
+
+const LOOPBACK_HOSTS = new Set(['localhost', '127.0.0.1', '[::1]', '0.0.0.0']);
+
+const isLoopbackHost = (hostname: string): boolean =>
+  LOOPBACK_HOSTS.has(hostname);
+
+const isContainerServingApiUrl = async (
+  containerName: string,
+): Promise<boolean> => {
+  if (ConfigService.getActiveRemote() !== LOCAL_REMOTE_NAME) {
+    return false;
+  }
+
+  if (!isContainerRunning(containerName)) {
+    return false;
+  }
+
+  try {
+    const { apiUrl } = await new ConfigService().getConfig();
+    const { hostname, port: apiPort } = new URL(apiUrl);
+
+    return (
+      isLoopbackHost(hostname) &&
+      apiPort !== '' &&
+      String(getContainerPort(containerName)) === apiPort
+    );
+  } catch {
+    return false;
+  }
+};
+
+const resolveLocalServerVersion = async (
+  containerName: string,
+): Promise<string | null> => {
+  if (await isContainerServingApiUrl(containerName)) {
+    const dockerVersion = await getLocalServerVersion(containerName);
+
+    if (dockerVersion !== null) {
+      return dockerVersion;
+    }
+  }
+
+  return (
+    (await getServerVersionFromApi()) ??
+    (await getLocalServerVersion(containerName))
+  );
+};
+
 const MS_PER_DAY = 24 * 60 * 60 * 1000;
 
 // Fallback for versions older than the most recent ~100 Docker Hub tags:
@@ -17,8 +72,9 @@ export const getVersionInfo = async (
   containerName: string = CONTAINER_NAME,
 ): Promise<VersionInfo> => {
   const cliVersion = sdkPackageJson.version;
+
   const [localServerVersion, publishedVersions] = await Promise.all([
-    getLocalServerVersion(containerName),
+    resolveLocalServerVersion(containerName),
     getPublishedServerVersions(),
   ]);
   const latestServerVersion = publishedVersions[0]?.name ?? null;