diff --git a/wagon-providers/wagon-ssh-external/src/main/java/org/apache/maven/wagon/providers/ssh/external/ScpExternalWagon.java b/wagon-providers/wagon-ssh-external/src/main/java/org/apache/maven/wagon/providers/ssh/external/ScpExternalWagon.java
index 0ab0cd29..a6234a70 100644
--- a/wagon-providers/wagon-ssh-external/src/main/java/org/apache/maven/wagon/providers/ssh/external/ScpExternalWagon.java
+++ b/wagon-providers/wagon-ssh-external/src/main/java/org/apache/maven/wagon/providers/ssh/external/ScpExternalWagon.java
@@ -229,7 +229,18 @@ private void executeScpCommand(Resource resource, File localFile, boolean put)
         }
         Commandline cl = createBaseCommandLine(putty, scpExecutable, privateKey);
 
-        cl.setWorkingDirectory(localFile.getParentFile().getAbsolutePath());
+        File parentFile = localFile.getParentFile();
+        if (null == parentFile) {
+            try {
+                File abs = localFile.getAbsoluteFile();
+                parentFile = abs.getParentFile();
+            } catch (SecurityException e) {
+                fireTransferError(resource, e, put ? TransferEvent.REQUEST_PUT : TransferEvent.REQUEST_GET);
+
+                throw new TransferFailedException("Error accessing absolute path of " + localFile, e);
+            }
+        }
+        cl.setWorkingDirectory(parentFile.getAbsolutePath());
 
         int port =
                 repository.getPort() == WagonConstants.UNKNOWN_PORT ? ScpHelper.DEFAULT_SSH_PORT : repository.getPort();