diff --git a/app/src/main/java/io/homeassistant/companion/android/notifications/MessagingManager.kt b/app/src/main/java/io/homeassistant/companion/android/notifications/MessagingManager.kt
index 076bce24da6..2cbf45bea1a 100644
--- a/app/src/main/java/io/homeassistant/companion/android/notifications/MessagingManager.kt
+++ b/app/src/main/java/io/homeassistant/companion/android/notifications/MessagingManager.kt
@@ -48,6 +48,7 @@ import dagger.hilt.android.qualifiers.ApplicationContext
 import io.homeassistant.companion.android.R
 import io.homeassistant.companion.android.authenticator.Authenticator
 import io.homeassistant.companion.android.common.R as commonR
+import io.homeassistant.companion.android.common.data.HomeAssistantApis
 import io.homeassistant.companion.android.common.data.prefs.PrefsRepository
 import io.homeassistant.companion.android.common.data.servers.ServerManager
 import io.homeassistant.companion.android.common.notifications.DeviceCommandData
@@ -1256,7 +1257,7 @@ class MessagingManager @Inject constructor(
         withContext(
             Dispatchers.IO
         ) {
-            if (url == null || url.path.endsWith("gif").not()) {
+            if (url == null || !isGif(url, requiresAuth, serverId)) {
                 return@withContext null
             }
 
@@ -1287,6 +1288,64 @@ class MessagingManager @Inject constructor(
             return@withContext FileProvider.getUriForFile(context, "${context.packageName}.provider", file)
         }
 
+    private suspend fun isGif(url: URL, requiresAuth: Boolean = false, serverId: Int): Boolean {
+        withContext(
+            Dispatchers.IO
+        ) {
+            try {
+                Log.d(TAG, "Checking URL: $url")
+
+                if (url.protocol == "http" || url.protocol == "https") {
+                    Log.d(TAG, "It's an http URL")
+
+                    val client = OkHttpClient()
+                    val requestBuilder = Request.Builder().apply {
+                        url(url)
+                        addHeader("User-Agent", HomeAssistantApis.USER_AGENT_STRING)
+                        if (requiresAuth) {
+                            Log.d(TAG, "Authorization required!")
+                            val authToken = serverManager.authenticationRepository(serverId).buildBearerToken()
+                            addHeader("Authorization", authToken)
+                            Log.d(TAG, "Auth Token: $authToken")
+                        }
+                    }
+
+                    // Try with HEAD method first
+                    val headRequest = requestBuilder.method("HEAD", null).head().build()
+                    val headResponse = client.newCall(headRequest).execute()
+
+                    val responseCode = headResponse.code
+                    val contentType = headResponse.header("Content-Type")
+
+                    Log.d(TAG, "Response Code (HEAD): $responseCode")
+                    Log.d(TAG, "Content-Type (HEAD): $contentType")
+
+                    headResponse.close()
+
+                    if (responseCode == 405) {
+                        Log.d(TAG, "HEAD method not allowed, retrying with GET")
+                        // Retry with GET method
+                        val getRequest = requestBuilder.method("HEAD", null).head().build()
+                        val getResponse = client.newCall(getRequest).execute()
+                        val getContentType = getResponse.header("Content-Type")
+                        val getResponseCode = getResponse.code
+                        getResponse.close()
+                        Log.d(TAG, "Response Code (GET): $getResponseCode")
+                        Log.d(TAG, "Content-Type (GET): $getContentType")
+                        return getContentType != null && getContentType.startsWith("image/gif")
+                    } else {
+                        val contentType = headResponse.header("Content-Type")
+                        Log.d(TAG, "Content-Type (HEAD): $contentType")
+                        return contentType != null && contentType.startsWith("image/gif")
+                    }
+                }
+            } catch (e: Exception) {
+                Log.e(TAG, "Error checking content type", e)
+            }
+            return false
+        }
+    }
+
     private suspend fun handleVideo(
         builder: NotificationCompat.Builder,
         data: Map<String, String>