diff --git a/esphome/components/web_server/web_server.cpp b/esphome/components/web_server/web_server.cpp
index f576507c0f..77c20b956b 100644
--- a/esphome/components/web_server/web_server.cpp
+++ b/esphome/components/web_server/web_server.cpp
@@ -125,7 +125,16 @@ void DeferredUpdateEventSource::process_deferred_queue_() {
     if (this->send(message.c_str(), "state") != DISCARDED) {
       // O(n) but memory efficiency is more important than speed here which is why std::vector was chosen
       deferred_queue_.erase(deferred_queue_.begin());
+      this->consecutive_send_failures_ = 0;  // Reset failure count on successful send
     } else {
+      this->consecutive_send_failures_++;
+      if (this->consecutive_send_failures_ >= MAX_CONSECUTIVE_SEND_FAILURES) {
+        // Too many failures, connection is likely dead
+        ESP_LOGW(TAG, "Closing stuck EventSource connection after %" PRIu16 " failed sends",
+                 this->consecutive_send_failures_);
+        this->close();
+        this->deferred_queue_.clear();
+      }
       break;
     }
   }
@@ -164,6 +173,8 @@ void DeferredUpdateEventSource::deferrable_send_state(void *source, const char *
     std::string message = message_generator(web_server_, source);
     if (this->send(message.c_str(), "state") == DISCARDED) {
       deq_push_back_with_dedup_(source, message_generator);
+    } else {
+      this->consecutive_send_failures_ = 0;  // Reset failure count on successful send
     }
   }
 }
diff --git a/esphome/components/web_server/web_server.h b/esphome/components/web_server/web_server.h
index c654d83bbd..82b31ab656 100644
--- a/esphome/components/web_server/web_server.h
+++ b/esphome/components/web_server/web_server.h
@@ -127,6 +127,8 @@ class DeferredUpdateEventSource : public AsyncEventSource {
   // footprint is more important than speed here)
   std::vector<DeferredEvent> deferred_queue_;
   WebServer *web_server_;
+  uint16_t consecutive_send_failures_{0};
+  static constexpr uint16_t MAX_CONSECUTIVE_SEND_FAILURES = 2500;  // ~20 seconds at 125Hz loop rate
 
   // helper for allowing only unique entries in the queue
   void deq_push_back_with_dedup_(void *source, message_generator_t *message_generator);