diff --git a/server/stream_session.cpp b/server/stream_session.cpp
index 3fb149e6..ca796a5b 100644
--- a/server/stream_session.cpp
+++ b/server/stream_session.cpp
@@ -129,6 +129,7 @@ void StreamSession::stop()
 void StreamSession::send_next()
 {
     auto& buffer = messages_.front();
+    buffer.on_air = true;
     boost::asio::async_write(socket_, buffer,
                              boost::asio::bind_executor(strand_, [ this, self = shared_from_this(), buffer ](boost::system::error_code ec, std::size_t length) {
                                  messages_.pop_front();
@@ -148,19 +149,15 @@ void StreamSession::sendAsync(shared_const_buffer const_buf, bool send_now)
 {
     strand_.post([ this, self = shared_from_this(), const_buf, send_now ]() {
         // delete PCM chunks that are older than the overall buffer duration
-        if (messages_.size() > 1)
-        {
-            // don't remove the first message as it might beeing sent already
-            messages_.erase(std::remove_if(messages_.begin() + 1, messages_.end(),
-                                           [this](const shared_const_buffer& buffer) {
-                                               const auto& msg = buffer.message();
-                                               if (!msg.is_pcm_chunk)
-                                                   return false;
-                                               auto age = chronos::clk::now() - msg.rec_time;
-                                               return (age > std::chrono::milliseconds(bufferMs_) + 100ms);
-                                           }),
-                            messages_.end());
-        }
+        messages_.erase(std::remove_if(messages_.begin() + 1, messages_.end(),
+                                       [this](const shared_const_buffer& buffer) {
+                                           const auto& msg = buffer.message();
+                                           if (!msg.is_pcm_chunk || buffer.on_air)
+                                               return false;
+                                           auto age = chronos::clk::now() - msg.rec_time;
+                                           return (age > std::chrono::milliseconds(bufferMs_) + 100ms);
+                                       }),
+                        messages_.end());
 
         if (send_now)
             messages_.push_front(const_buf);
diff --git a/server/stream_session.hpp b/server/stream_session.hpp
index fa5766c5..c31508fb 100644
--- a/server/stream_session.hpp
+++ b/server/stream_session.hpp
@@ -59,7 +59,7 @@ class shared_const_buffer
     };
 
 public:
-    shared_const_buffer(msg::BaseMessage& message)
+    shared_const_buffer(msg::BaseMessage& message) : on_air(false)
     {
         tv t;
         message.sent = t;
@@ -94,6 +94,8 @@ public:
         return *message_;
     }
 
+    bool on_air;
+
 private:
     std::shared_ptr<Message> message_;
     boost::asio::const_buffer buffer_;