diff --git a/src/c/core/session/session.c b/src/c/core/session/session.c
index 45900b1a0..2de8d0608 100644
--- a/src/c/core/session/session.c
+++ b/src/c/core/session/session.c
@@ -629,7 +629,11 @@ void uxr_flash_output_streams(
         while (uxr_prepare_next_reliable_buffer_to_send(stream, &buffer, &length, &seq_num))
         {
             uxr_stamp_session_header(&session->info, id.raw, seq_num, buffer);
-            send_message(session, buffer, length);
+            if (!send_message(session, buffer, length))
+            {
+                uxr_cancel_reliable_buffer_to_send(stream, seq_num);
+                break;
+            }
         }
 
         UXR_UNLOCK_STREAM_ID(session, id);
diff --git a/src/c/core/session/stream/output_reliable_stream.c b/src/c/core/session/stream/output_reliable_stream.c
index 93ca6e25a..ce5402226 100644
--- a/src/c/core/session/stream/output_reliable_stream.c
+++ b/src/c/core/session/stream/output_reliable_stream.c
@@ -192,6 +192,19 @@ bool uxr_prepare_next_reliable_buffer_to_send(
     return data_to_send;
 }
 
+void uxr_cancel_reliable_buffer_to_send(
+        uxrOutputReliableStream* stream,
+        uxrSeqNum seq_num)
+{
+    uxrSeqNum next_seq_num = uxr_seq_num_add(seq_num, 1);
+    stream->last_sent = uxr_seq_num_sub(seq_num, 1);
+    if (stream->last_written == next_seq_num &&
+            stream->offset == uxr_get_reliable_buffer_size(&stream->base, next_seq_num))
+    {
+        stream->last_written = seq_num;
+    }
+}
+
 bool uxr_update_output_stream_heartbeat_timestamp(
         uxrOutputReliableStream* stream,
         int64_t current_timestamp)
diff --git a/src/c/core/session/stream/output_reliable_stream_internal.h b/src/c/core/session/stream/output_reliable_stream_internal.h
index 744b02f3d..7ba6ffa09 100644
--- a/src/c/core/session/stream/output_reliable_stream_internal.h
+++ b/src/c/core/session/stream/output_reliable_stream_internal.h
@@ -45,6 +45,9 @@ bool uxr_prepare_next_reliable_buffer_to_send(
         uint8_t** buffer,
         size_t* length,
         uxrSeqNum* seq_num);
+void uxr_cancel_reliable_buffer_to_send(
+        uxrOutputReliableStream* stream,
+        uxrSeqNum seq_num);
 
 bool uxr_update_output_stream_heartbeat_timestamp(
         uxrOutputReliableStream* stream,
diff --git a/test/unitary/session/Session.cpp b/test/unitary/session/Session.cpp
index 9756c5428..7a6973179 100644
--- a/test/unitary/session/Session.cpp
+++ b/test/unitary/session/Session.cpp
@@ -103,6 +103,7 @@ class SessionTest : public testing::Test
     uint8_t input_reliable_buffer[MTU * HISTORY];
 
     static int listening_counter;
+    static int sending_counter;
 
     static bool send_msg(
             void* instance,
@@ -124,6 +125,13 @@ class SessionTest : public testing::Test
             EXPECT_EQ(size_t(MTU), len);
             return false;
         }
+        else if (std::string("FlashReliableStreamSendError") ==
+                ::testing::UnitTest::GetInstance()->current_test_info()->name())
+        {
+            EXPECT_EQ(size_t(OFFSET + SUBHEADER_SIZE + 8), len);
+            SessionTest::sending_counter++;
+            return false;
+        }
         else if (std::string("SendHeartbeat") == ::testing::UnitTest::GetInstance()->current_test_info()->name())
         {
             EXPECT_EQ(size_t(HEARTBEAT_MAX_MSG_SIZE - (MAX_HEADER_SIZE - OFFSET)), len);
@@ -272,6 +280,7 @@ class SessionTest : public testing::Test
 
 SessionTest* SessionTest::current = nullptr;
 int SessionTest::listening_counter;
+int SessionTest::sending_counter;
 
 TEST_F(SessionTest, SetStatusCallback)
 {
@@ -355,6 +364,28 @@ TEST_F(SessionTest, FlashStreams)
     uxr_flash_output_streams(&session);
 }
 
+TEST_F(SessionTest, FlashReliableStreamSendError)
+{
+    SessionTest::sending_counter = 0;
+
+    ucdrBuffer ub;
+    uxrStreamId output_reliable = uxr_stream_id(0, UXR_RELIABLE_STREAM, UXR_OUTPUT_STREAM);
+    (void) uxr_prepare_stream_to_write_submessage(&session, output_reliable, 8, &ub, 1, 0);
+
+    uxrOutputReliableStream* stream = &session.streams.output_reliable[0];
+    uxr_flash_output_streams(&session);
+
+    EXPECT_EQ(1, SessionTest::sending_counter);
+    EXPECT_EQ(SEQ_NUM_MAX, stream->last_sent);
+    EXPECT_EQ(0u, stream->last_written);
+
+    uxr_flash_output_streams(&session);
+
+    EXPECT_EQ(2, SessionTest::sending_counter);
+    EXPECT_EQ(SEQ_NUM_MAX, stream->last_sent);
+    EXPECT_EQ(0u, stream->last_written);
+}
+
 TEST_F(SessionTest, WaitSessionStatusBad)
 {
     // The OK version is already checked with the CreateOk and DeleteOk test versions