diff --git a/cli/src/services/session.service.ts b/cli/src/services/session.service.ts
index c9eae671fd..0235b30a4c 100644
--- a/cli/src/services/session.service.ts
+++ b/cli/src/services/session.service.ts
@@ -3,6 +3,7 @@ import { access, constants, mkdir, readFile, unlink, writeFile } from 'node:fs/p
 import path from 'node:path';
 import yaml from 'yaml';
 import { ImmichApi } from './api.service';
+
 class LoginError extends Error {
   constructor(message: string) {
     super(message);
@@ -14,14 +15,12 @@ class LoginError extends Error {
 }
 
 export class SessionService {
-  readonly configDirectory!: string;
-  readonly authPath!: string;
-
-  constructor(configDirectory: string) {
-    this.configDirectory = configDirectory;
-    this.authPath = path.join(configDirectory, '/auth.yml');
+  private get authPath() {
+    return path.join(this.configDirectory, '/auth.yml');
   }
 
+  constructor(private configDirectory: string) {}
+
   async connect(): Promise<ImmichApi> {
     let instanceUrl = process.env.IMMICH_INSTANCE_URL;
     let apiKey = process.env.IMMICH_API_KEY;
@@ -48,6 +47,8 @@ export class SessionService {
       }
     }
 
+    instanceUrl = await this.resolveApiEndpoint(instanceUrl);
+
     const api = new ImmichApi(instanceUrl, apiKey);
 
     const pingResponse = await api.pingServer().catch((error) => {
@@ -62,7 +63,9 @@ export class SessionService {
   }
 
   async login(instanceUrl: string, apiKey: string): Promise<ImmichApi> {
-    console.log('Logging in...');
+    console.log(`Logging in to ${instanceUrl}`);
+
+    instanceUrl = await this.resolveApiEndpoint(instanceUrl);
 
     const api = new ImmichApi(instanceUrl, apiKey);
 
@@ -83,7 +86,7 @@ export class SessionService {
 
     await writeFile(this.authPath, yaml.stringify({ instanceUrl, apiKey }), { mode: 0o600 });
 
-    console.log('Wrote auth info to ' + this.authPath);
+    console.log(`Wrote auth info to ${this.authPath}`);
 
     return api;
   }
@@ -98,4 +101,18 @@ export class SessionService {
 
     console.log('Successfully logged out');
   }
+
+  private async resolveApiEndpoint(instanceUrl: string): Promise<string> {
+    const wellKnownUrl = new URL('.well-known/immich', instanceUrl);
+    try {
+      const wellKnown = await fetch(wellKnownUrl).then((response) => response.json());
+      const endpoint = new URL(wellKnown.api.endpoint, instanceUrl).toString();
+      if (endpoint !== instanceUrl) {
+        console.debug(`Discovered API at ${endpoint}`);
+      }
+      return endpoint;
+    } catch {
+      return instanceUrl;
+    }
+  }
 }
diff --git a/e2e/src/cli/specs/login.e2e-spec.ts b/e2e/src/cli/specs/login.e2e-spec.ts
index e3140ecea9..aa27bec63e 100644
--- a/e2e/src/cli/specs/login.e2e-spec.ts
+++ b/e2e/src/cli/specs/login.e2e-spec.ts
@@ -29,12 +29,12 @@ describe(`immich login-key`, () => {
     expect(exitCode).toBe(1);
   });
 
-  it('should login', async () => {
+  it('should login and save auth.yml with 600', async () => {
     const admin = await apiUtils.adminSetup();
     const key = await apiUtils.createApiKey(admin.accessToken);
     const { stdout, stderr, exitCode } = await immichCli(['login-key', app, `${key.secret}`]);
     expect(stdout.split('\n')).toEqual([
-      'Logging in...',
+      'Logging in to http://127.0.0.1:2283/api',
       'Logged in as admin@immich.cloud',
       'Wrote auth info to /tmp/immich/auth.yml',
     ]);
@@ -45,4 +45,18 @@ describe(`immich login-key`, () => {
     const mode = (stats.mode & 0o777).toString(8);
     expect(mode).toEqual('600');
   });
+
+  it('should login without /api in the url', async () => {
+    const admin = await apiUtils.adminSetup();
+    const key = await apiUtils.createApiKey(admin.accessToken);
+    const { stdout, stderr, exitCode } = await immichCli(['login-key', app.replaceAll('/api', ''), `${key.secret}`]);
+    expect(stdout.split('\n')).toEqual([
+      'Logging in to http://127.0.0.1:2283',
+      'Discovered API at http://127.0.0.1:2283/api',
+      'Logged in as admin@immich.cloud',
+      'Wrote auth info to /tmp/immich/auth.yml',
+    ]);
+    expect(stderr).toBe('');
+    expect(exitCode).toBe(0);
+  });
 });