diff --git a/src/DIRAC/DataManagementSystem/Client/DataManager.py b/src/DIRAC/DataManagementSystem/Client/DataManager.py
index f414501e0c0..75f51ce972e 100644
--- a/src/DIRAC/DataManagementSystem/Client/DataManager.py
+++ b/src/DIRAC/DataManagementSystem/Client/DataManager.py
@@ -26,6 +26,7 @@
 from DIRAC.Core.Utilities.ReturnValues import returnSingleResult
 from DIRAC.Core.Security.ProxyInfo import getProxyInfo
 from DIRAC.ConfigurationSystem.Client.Helpers.Operations import Operations
+from DIRAC.DataManagementSystem.Client import MAX_FILENAME_LENGTH
 from DIRAC.MonitoringSystem.Client.DataOperationSender import DataOperationSender
 from DIRAC.DataManagementSystem.Utilities.DMSHelpers import DMSHelpers
 from DIRAC.Resources.Catalog.FileCatalog import FileCatalog
@@ -433,6 +434,9 @@ def putAndRegister(self, lfn, fileName, diracSE, guid=None, path=None, checksum=
         'overwrite' removes file from the file catalogue and SE before attempting upload
         """
 
+        if len(os.path.basename(lfn)) > MAX_FILENAME_LENGTH:
+            return S_ERROR(errno.ENAMETOOLONG, f"maximum {MAX_FILENAME_LENGTH} characters allowed")
+
         res = self.__hasAccess("addFile", lfn)
         if not res["OK"]:
             return res
diff --git a/src/DIRAC/DataManagementSystem/Client/FailoverTransfer.py b/src/DIRAC/DataManagementSystem/Client/FailoverTransfer.py
index c3fa6e685ae..7f65c1c433d 100644
--- a/src/DIRAC/DataManagementSystem/Client/FailoverTransfer.py
+++ b/src/DIRAC/DataManagementSystem/Client/FailoverTransfer.py
@@ -16,6 +16,8 @@
     temporary replica.
 
 """
+
+import errno
 import time
 
 from DIRAC import S_OK, S_ERROR, gLogger
@@ -107,6 +109,9 @@ def transferAndRegisterFile(
                     break
                 elif cmpError(result, EFCERR):
                     self.log.debug("transferAndRegisterFile: FC unavailable, retry")
+                elif cmpError(result, errno.ENAMETOOLONG):
+                    self.log.debug(f"transferAndRegisterFile: this file won't be uploaded: {result}")
+                    return result
                 elif retryUpload and len(destinationSEList) == 1:
                     self.log.debug("transferAndRegisterFile: Failed uploading to the only SE, retry")
                 else:
diff --git a/src/DIRAC/DataManagementSystem/Client/__init__.py b/src/DIRAC/DataManagementSystem/Client/__init__.py
index 6f5707ba432..f06ddfbf90b 100755
--- a/src/DIRAC/DataManagementSystem/Client/__init__.py
+++ b/src/DIRAC/DataManagementSystem/Client/__init__.py
@@ -1,3 +1,6 @@
 """
    DIRAC.DataManagementSystem.Client package
 """
+
+#: Maximum number of characters for a filename, this should be the same as the FileName column of the DFC
+MAX_FILENAME_LENGTH = 128