diff --git a/WordPress/build.gradle b/WordPress/build.gradle
index bca68ced51e8..739eef69b74a 100644
--- a/WordPress/build.gradle
+++ b/WordPress/build.gradle
@@ -97,6 +97,7 @@ repositories {
             includeGroup "com.automattic"
             includeGroup "com.automattic.tracks"
             includeGroup "com.gravatar"
+            includeGroup "rs.wordpress.api"
         }
     }
     maven {
@@ -521,6 +522,8 @@ dependencies {
     implementation "com.google.dagger:hilt-android:$gradle.ext.daggerVersion"
     ksp "com.google.dagger:hilt-compiler:$gradle.ext.daggerVersion"
 
+    implementation("rs.wordpress.api:android:$wordPressRsVersion")
+
     testImplementation("androidx.arch.core:core-testing:$androidxArchCoreVersion", {
         exclude group: 'com.android.support', module: 'support-compat'
         exclude group: 'com.android.support', module: 'support-annotations'
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/accounts/LoginActivity.java b/WordPress/src/main/java/org/wordpress/android/ui/accounts/LoginActivity.java
index d05569590636..bb4aee4850b8 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/accounts/LoginActivity.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/accounts/LoginActivity.java
@@ -4,6 +4,7 @@
 import android.content.Intent;
 import android.net.Uri;
 import android.os.Bundle;
+import android.util.Log;
 import android.view.MenuItem;
 
 import androidx.annotation.NonNull;
@@ -20,6 +21,7 @@
 
 import org.wordpress.android.R;
 import org.wordpress.android.analytics.AnalyticsTracker;
+import org.wordpress.android.analytics.AnalyticsTracker.Stat;
 import org.wordpress.android.fluxc.model.SiteModel;
 import org.wordpress.android.fluxc.network.MemorizingTrustManager;
 import org.wordpress.android.fluxc.store.AccountStore.AuthEmailPayloadScheme;
@@ -652,6 +654,16 @@ public void gotXmlRpcEndpoint(String inputSiteAddress, String endpointAddress) {
         LoginUsernamePasswordFragment loginUsernamePasswordFragment =
                 LoginUsernamePasswordFragment.newInstance(inputSiteAddress, endpointAddress, null, null, false);
         slideInFragment(loginUsernamePasswordFragment, true, LoginUsernamePasswordFragment.TAG);
+
+        // In the background, run the API discovery test to see if we can add this site for the REST API
+        try {
+            String authorizationUrl = mViewModel.runApiDiscoveryTest(inputSiteAddress);
+            Log.d("WP_RS", "Found authorization URL: " + authorizationUrl);
+            AnalyticsTracker.track(Stat.BACKGROUND_REST_AUTODISCOVERY_SUCCESSFUL);
+        } catch (Exception ex) {
+            Log.e("WP_RS", "Unable to find authorization URL:" + ex.getMessage());
+            AnalyticsTracker.track(Stat.BACKGROUND_REST_AUTODISCOVERY_FAILED);
+        }
     }
 
     @Override
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/accounts/LoginViewModel.kt b/WordPress/src/main/java/org/wordpress/android/ui/accounts/LoginViewModel.kt
index b717efbbaf67..14499636c2dd 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/accounts/LoginViewModel.kt
+++ b/WordPress/src/main/java/org/wordpress/android/ui/accounts/LoginViewModel.kt
@@ -3,12 +3,14 @@ package org.wordpress.android.ui.accounts
 import androidx.lifecycle.LiveData
 import androidx.lifecycle.MediatorLiveData
 import androidx.lifecycle.ViewModel
+import kotlinx.coroutines.runBlocking
 import org.wordpress.android.fluxc.store.AccountStore.AuthEmailPayloadScheme
 import org.wordpress.android.fluxc.store.SiteStore.ConnectSiteInfoPayload
 import org.wordpress.android.ui.accounts.LoginNavigationEvents.ShowNoJetpackSites
 import org.wordpress.android.ui.accounts.LoginNavigationEvents.ShowSiteAddressError
 import org.wordpress.android.util.BuildConfigWrapper
 import org.wordpress.android.viewmodel.Event
+import rs.wordpress.api.kotlin.WpLoginClient
 import javax.inject.Inject
 import kotlin.text.RegexOption.IGNORE_CASE
 
@@ -31,4 +33,9 @@ class LoginViewModel @Inject constructor(private val buildConfigWrapper: BuildCo
     } else {
         AuthEmailPayloadScheme.WORDPRESS
     }
+
+    fun runApiDiscoveryTest(input: String) = runBlocking {
+        val urlDiscovery = WpLoginClient().apiDiscovery(input)
+        urlDiscovery.getOrThrow().apiDetails.findApplicationPasswordsAuthenticationUrl()
+    }
 }
diff --git a/build.gradle b/build.gradle
index 2e1aada224f2..9407e539aaff 100644
--- a/build.gradle
+++ b/build.gradle
@@ -31,6 +31,7 @@ ext {
     wordPressFluxCVersion = 'trunk-94d25d35fb4bf58a2e90741a6a5d56b8c6c3ce42'
     wordPressLoginVersion = '1.16.0'
     wordPressPersistentEditTextVersion = '1.0.2'
+    wordPressRsVersion = 'trunk-50f703a7f677084157d02f05d4d477d7eaf960b1'
     wordPressUtilsVersion = '3.14.0'
     indexosMediaForMobileVersion = '43a9026f0973a2f0a74fa813132f6a16f7499c3a'
     gravatarVersion = '1.0.0'
@@ -43,7 +44,7 @@ ext {
     androidxArchCoreVersion = '2.2.0'
     androidxCameraVersion = '1.3.4'
     androidxComposeBomVersion = '2024.08.00'
-    androidxComposeCompilerVersion = '1.5.9'
+    androidxComposeCompilerVersion = '1.5.14'
     androidxComposeNavigationVersion = '2.7.7'
     androidxCardviewVersion = '1.0.0'
     androidxConstraintlayoutVersion = '2.1.4'
diff --git a/libs/analytics/src/main/java/org/wordpress/android/analytics/AnalyticsTracker.java b/libs/analytics/src/main/java/org/wordpress/android/analytics/AnalyticsTracker.java
index 6c2586b02e5c..9cecd6b3b3da 100644
--- a/libs/analytics/src/main/java/org/wordpress/android/analytics/AnalyticsTracker.java
+++ b/libs/analytics/src/main/java/org/wordpress/android/analytics/AnalyticsTracker.java
@@ -1147,8 +1147,9 @@ public enum Stat {
         VOICE_TO_CONTENT_BUTTON_DONE_TAPPED,
         VOICE_TO_CONTENT_BUTTON_UPGRADE_TAPPED,
         VOICE_TO_CONTENT_BUTTON_CLOSE_TAPPED,
-        VOICE_TO_CONTENT_BUTTON_RECORDING_LIMIT_REACHED;
-
+        VOICE_TO_CONTENT_BUTTON_RECORDING_LIMIT_REACHED,
+        BACKGROUND_REST_AUTODISCOVERY_SUCCESSFUL,
+        BACKGROUND_REST_AUTODISCOVERY_FAILED;
         /*
          * Please set the event name in the enum only if the new Stat's name in lower case does not match it.
          * In that case you also need to add the event in the `AnalyticsTrackerNosaraTest.specialNames` map.
diff --git a/settings.gradle b/settings.gradle
index a525db2b0406..98d3414f0359 100644
--- a/settings.gradle
+++ b/settings.gradle
@@ -1,6 +1,6 @@
 pluginManagement {
-    gradle.ext.kotlinVersion = '1.9.22'
-    gradle.ext.kspVersion = '1.9.22-1.0.17'
+    gradle.ext.kotlinVersion = '1.9.24'
+    gradle.ext.kspVersion = '1.9.24-1.0.20'
     gradle.ext.agpVersion = '8.5.1'
     gradle.ext.googleServicesVersion = '4.3.15'
     gradle.ext.navigationVersion = '2.7.7'