diff --git a/libuavcan/include/uavcan/error.hpp b/libuavcan/include/uavcan/error.hpp
index bce8b4ed00..3776f27b8e 100644
--- a/libuavcan/include/uavcan/error.hpp
+++ b/libuavcan/include/uavcan/error.hpp
@@ -33,6 +33,7 @@ const int16_t ErrNotInited               = 8;
 const int16_t ErrRecursiveCall           = 9;
 const int16_t ErrLogic                   = 10;
 const int16_t ErrPassiveMode             = 11;  ///< Operation not permitted in passive mode
+const int16_t ErrTransferTooLong         = 12;  ///< Transfer of this length cannot be sent with given transfer type
 /**
  * @}
  */
diff --git a/libuavcan/src/transport/uc_transfer_sender.cpp b/libuavcan/src/transport/uc_transfer_sender.cpp
index 31315073c2..f75b3cc149 100644
--- a/libuavcan/src/transport/uc_transfer_sender.cpp
+++ b/libuavcan/src/transport/uc_transfer_sender.cpp
@@ -21,8 +21,7 @@ int TransferSender::send(const uint8_t* payload, unsigned payload_len, Monotonic
 {
     if (payload_len > getMaxPayloadLenForTransferType(transfer_type))
     {
-        UAVCAN_ASSERT(0);
-        return -ErrInvalidParam;
+        return -ErrTransferTooLong;
     }
 
     Frame frame(data_type_.getID(), transfer_type, dispatcher_.getNodeID(), dst_node_id, 0, tid);
@@ -129,6 +128,12 @@ int TransferSender::send(const uint8_t* payload, unsigned payload_len, Monotonic
 int TransferSender::send(const uint8_t* payload, unsigned payload_len, MonotonicTime tx_deadline,
                          MonotonicTime blocking_deadline, TransferType transfer_type, NodeID dst_node_id)
 {
+    // This check must be performed before TID is incremented to avoid skipping TID values on failures
+    if (payload_len > getMaxPayloadLenForTransferType(transfer_type))
+    {
+        return -ErrTransferTooLong;
+    }
+
     const OutgoingTransferRegistryKey otr_key(data_type_.getID(), transfer_type, dst_node_id);
 
     UAVCAN_ASSERT(!tx_deadline.isZero());