diff --git a/cli/src/configuration.ts b/cli/src/configuration.ts
index dc3813cb..691b2839 100644
--- a/cli/src/configuration.ts
+++ b/cli/src/configuration.ts
@@ -12,7 +12,7 @@ import packageJson from '../package.json'
 import { getCliArgs } from '@/utils/cliArgs'
 
 class Configuration {
-    public readonly serverUrl: string
+    private _serverUrl: string
     private _cliApiToken: string
     public readonly isDaemonProcess: boolean
 
@@ -29,7 +29,7 @@ class Configuration {
 
     constructor() {
         // Server configuration
-        this.serverUrl = process.env.HAPI_SERVER_URL || 'http://localhost:3006'
+        this._serverUrl = process.env.HAPI_SERVER_URL || 'http://localhost:3006'
         this._cliApiToken = process.env.CLI_API_TOKEN || ''
 
         // Check if we're running as daemon based on process args
@@ -64,6 +64,14 @@ class Configuration {
         }
     }
 
+    get serverUrl(): string {
+        return this._serverUrl
+    }
+
+    _setServerUrl(url: string): void {
+        this._serverUrl = url
+    }
+
     get cliApiToken(): string {
         return this._cliApiToken
     }
diff --git a/cli/src/persistence.ts b/cli/src/persistence.ts
index 9be53326..5942db54 100644
--- a/cli/src/persistence.ts
+++ b/cli/src/persistence.ts
@@ -17,6 +17,8 @@ interface Settings {
   machineIdConfirmedByServer?: boolean
   daemonAutoStartWhenRunningHappy?: boolean
   cliApiToken?: string
+  // Server URL for API connections (priority: env HAPI_SERVER_URL > this > default)
+  serverUrl?: string
 }
 
 const defaultSettings: Settings = {}
diff --git a/cli/src/ui/serverUrlInit.ts b/cli/src/ui/serverUrlInit.ts
new file mode 100644
index 00000000..cc65d5cb
--- /dev/null
+++ b/cli/src/ui/serverUrlInit.ts
@@ -0,0 +1,31 @@
+/**
+ * Server URL initialization module
+ *
+ * Handles HAPI_SERVER_URL initialization with priority:
+ * 1. Environment variable (highest - allows temporary override)
+ * 2. Settings file (~/.hapi/settings.json)
+ * 3. Default value (http://localhost:3006)
+ */
+
+import { configuration } from '@/configuration'
+import { readSettings } from '@/persistence'
+
+/**
+ * Initialize server URL
+ * Must be called before any API operations
+ */
+export async function initializeServerUrl(): Promise<void> {
+    // 1. Environment variable has highest priority (allows temporary override)
+    if (process.env.HAPI_SERVER_URL) {
+        return
+    }
+
+    // 2. Read from settings file
+    const settings = await readSettings()
+    if (settings.serverUrl) {
+        configuration._setServerUrl(settings.serverUrl)
+        return
+    }
+
+    // 3. Default value already set in configuration constructor
+}
diff --git a/cli/src/ui/tokenInit.ts b/cli/src/ui/tokenInit.ts
index bd0daf90..337f7b9b 100644
--- a/cli/src/ui/tokenInit.ts
+++ b/cli/src/ui/tokenInit.ts
@@ -12,12 +12,16 @@ import { stdin as input, stdout as output } from 'node:process'
 import chalk from 'chalk'
 import { configuration } from '@/configuration'
 import { readSettings, updateSettings } from '@/persistence'
+import { initializeServerUrl } from '@/ui/serverUrlInit'
 
 /**
  * Initialize CLI API token
  * Must be called before any API operations
  */
 export async function initializeToken(): Promise<void> {
+    // Initialize server URL first (env > settings.json > default)
+    await initializeServerUrl()
+
     // 1. Environment variable has highest priority (allows temporary override)
     if (configuration.cliApiToken) {
         return
diff --git a/cli/src/utils/autoStartServer.ts b/cli/src/utils/autoStartServer.ts
index 1501df6a..c584c708 100644
--- a/cli/src/utils/autoStartServer.ts
+++ b/cli/src/utils/autoStartServer.ts
@@ -96,8 +96,16 @@ async function shouldAutoStartServer(): Promise<boolean> {
         return false
     }
 
-    // Condition 2: cliApiToken exists in settings.json (server was previously started)
+    // Condition 2: Check settings.json
     const settings = await readSettings()
+
+    // 2a: serverUrl is set in settings.json (user configured a specific server)
+    if (settings.serverUrl) {
+        logger.debug('[AUTO-START] serverUrl is set in settings.json, skipping auto-start')
+        return false
+    }
+
+    // 2b: cliApiToken exists in settings.json (server was previously started)
     if (!settings.cliApiToken) {
         logger.debug('[AUTO-START] No cliApiToken in settings, skipping auto-start')
         return false