diff --git a/.configure b/.configure
index 88cf56cf5997..18d6c18827f9 100644
--- a/.configure
+++ b/.configure
@@ -15,7 +15,7 @@
     },
     {
       "file": "android/debug.keystore",
-      "destination": "~/.configure/wordpress-android/secrets/debug_a8c.keystore",
+      "destination": "~/.configure/wordpress-android/secrets/debug.keystore",
       "encrypt": true
     },
     {
@@ -25,7 +25,7 @@
     },
     {
       "file": "android/automattic_upload.jks",
-      "destination": "WordPress/upload.jks",
+      "destination": "~/.configure/wordpress-android/secrets/upload.jks",
       "encrypt": true
     },
     {
diff --git a/WordPress/build.gradle b/WordPress/build.gradle
index 417b05ec667f..3ac8a6c85d2c 100644
--- a/WordPress/build.gradle
+++ b/WordPress/build.gradle
@@ -280,10 +280,12 @@ android {
     }
 
     signingConfigs {
-        if (["uploadStoreFile", "uploadStorePassword", "uploadKeyAlias", "uploadKeyPassword"].count { !gradle.ext.secretProperties.containsKey(it) } == 0) {
-            logger.info("App signing properties found in secrets.properties, configuring signing for release builds.")
+        def uploadKeystore = new File(gradle.ext.decryptedSecretsDir, "upload.jks")
+        def uploadCredentials = ["uploadStorePassword", "uploadKeyAlias", "uploadKeyPassword"]
+        if (uploadKeystore.exists() && uploadCredentials.every { gradle.ext.secretProperties.containsKey(it) }) {
+            logger.info("Upload keystore found, configuring signing for release builds.")
             release {
-                storeFile = rootProject.file(gradle.ext.secretProperties.get("uploadStoreFile"))
+                storeFile = uploadKeystore
                 storePassword = gradle.ext.secretProperties.get("uploadStorePassword")
                 keyAlias = gradle.ext.secretProperties.get("uploadKeyAlias")
                 keyPassword = gradle.ext.secretProperties.get("uploadKeyPassword")
@@ -291,13 +293,11 @@ android {
             android.buildTypes.release.signingConfig = android.signingConfigs.release
         }
 
-        if (gradle.ext.secretProperties.containsKey("debugStoreFile")) {
-            logger.info("Debug signing properties found in secrets.properties, configuring signing for debug builds.")
-            def sharedDebugStore = file(gradle.ext.secretProperties.get("debugStoreFile").replaceFirst("^~", System.getProperty("user.home")))
-            if (sharedDebugStore.exists()) {
-                debug {
-                    storeFile sharedDebugStore
-                }
+        def debugKeystore = new File(gradle.ext.decryptedSecretsDir, "debug.keystore")
+        if (debugKeystore.exists()) {
+            logger.info("Shared debug keystore found, configuring signing for debug builds.")
+            debug {
+                storeFile debugKeystore
             }
         }
     }
diff --git a/settings.gradle b/settings.gradle
index 527136368f0c..ef549373a030 100644
--- a/settings.gradle
+++ b/settings.gradle
@@ -20,7 +20,8 @@ plugins {
 gradle.ext {
     isCi = System.getenv('CI')?.toBoolean() ?: false
 
-    secretPath = "${System.getProperty("user.home")}/.configure/wordpress-android/secrets/secrets.properties"
+    decryptedSecretsDir = file("${System.getProperty("user.home")}/.configure/wordpress-android/secrets")
+    secretPath = new File(decryptedSecretsDir, "secrets.properties").path
     secretProperties = loadSecrets(
             logger,
             file("${rootDir}/defaults.properties"),