diff --git a/packages/twenty-sdk/src/cli/operations/server-start.ts b/packages/twenty-sdk/src/cli/operations/server-start.ts
index b0c8d505a0..2eb6f034fb 100644
--- a/packages/twenty-sdk/src/cli/operations/server-start.ts
+++ b/packages/twenty-sdk/src/cli/operations/server-start.ts
@@ -9,6 +9,7 @@ import {
   DEFAULT_PORT,
   DEFAULT_TEST_PORT,
   getContainerPort,
+  getDockerNotRunningMessage,
   IMAGE,
   isContainerRunning,
   TEST_CONTAINER_NAME,
@@ -148,11 +149,15 @@ const innerServerStart = async (
   }
 
   if (!checkDockerRunning()) {
+    const retryCommand = isTest
+      ? 'yarn twenty server start --test'
+      : 'yarn twenty server start';
+
     return {
       success: false,
       error: {
         code: SERVER_ERROR_CODES.DOCKER_NOT_RUNNING,
-        message: 'Docker is not running. Please start Docker and try again.',
+        message: getDockerNotRunningMessage(retryCommand),
       },
     };
   }
diff --git a/packages/twenty-sdk/src/cli/operations/server-upgrade.ts b/packages/twenty-sdk/src/cli/operations/server-upgrade.ts
index 55e79e6216..158fdcc29c 100644
--- a/packages/twenty-sdk/src/cli/operations/server-upgrade.ts
+++ b/packages/twenty-sdk/src/cli/operations/server-upgrade.ts
@@ -6,6 +6,7 @@ import {
   containerExists,
   getContainerDigest,
   getContainerPort,
+  getDockerNotRunningMessage,
   getImageDigest,
   getImageForVersion,
   TEST_CONTAINER_NAME,
@@ -30,11 +31,19 @@ const innerServerUpgrade = async (
   const { version = 'latest', test: isTest, onProgress } = options;
 
   if (!checkDockerRunning()) {
+    const retryCommand = [
+      'yarn twenty server upgrade',
+      version !== 'latest' ? version : null,
+      isTest ? '--test' : null,
+    ]
+      .filter(Boolean)
+      .join(' ');
+
     return {
       success: false,
       error: {
         code: SERVER_ERROR_CODES.DOCKER_NOT_RUNNING,
-        message: 'Docker is not running. Please start Docker and try again.',
+        message: getDockerNotRunningMessage(retryCommand),
       },
     };
   }
diff --git a/packages/twenty-sdk/src/cli/utilities/server/docker-container.ts b/packages/twenty-sdk/src/cli/utilities/server/docker-container.ts
index d48decc2d6..397fa1b5e2 100644
--- a/packages/twenty-sdk/src/cli/utilities/server/docker-container.ts
+++ b/packages/twenty-sdk/src/cli/utilities/server/docker-container.ts
@@ -103,3 +103,29 @@ export const checkDockerRunning = (): boolean => {
     return false;
   }
 };
+
+const getDockerStartInstruction = (): string => {
+  switch (process.platform) {
+    case 'darwin':
+      return '  Run: open -a Docker\n  (or launch Docker Desktop from Applications)';
+    case 'linux':
+      return '  Run: sudo systemctl start docker\n  (or launch Docker Desktop if installed)';
+    case 'win32':
+      return '  Launch Docker Desktop from the Start menu';
+    default:
+      return '  See https://docs.docker.com/engine/install/ for installation';
+  }
+};
+
+export const getDockerNotRunningMessage = (retryCommand: string): string =>
+  [
+    'Docker is not running.',
+    '',
+    'Start Docker:',
+    getDockerStartInstruction(),
+    '',
+    'Then retry:',
+    `  ${retryCommand}`,
+    '',
+    "Don't have Docker? Install from https://docs.docker.com/get-docker/",
+  ].join('\n');