diff --git a/lib/client/client.go b/lib/client/client.go
index 6d6d08f09f559..10765a50b9ef3 100644
--- a/lib/client/client.go
+++ b/lib/client/client.go
@@ -722,7 +722,15 @@ func (c *NodeClient) TransferFiles(ctx context.Context, cfg *sftp.Config) error
 	)
 	defer span.End()
 
-	return trace.Wrap(cfg.TransferFiles(ctx, c.Client.Client))
+	if err := cfg.TransferFiles(ctx, c.Client.Client); err != nil {
+		if trace.IsBadParameter(err) && strings.Contains(err.Error(), "expanding remote ~user paths is not supported") {
+			return trace.Wrap(&NonRetryableError{Err: err})
+		}
+
+		return trace.Wrap(err)
+	}
+
+	return nil
 }
 
 type netDialer interface {
diff --git a/lib/sshutils/sftp/sftp.go b/lib/sshutils/sftp/sftp.go
index b16eb656a3557..0d1b6a23fe8c5 100644
--- a/lib/sshutils/sftp/sftp.go
+++ b/lib/sshutils/sftp/sftp.go
@@ -329,7 +329,7 @@ func (c *Config) expandPaths(srcIsRemote, dstIsRemote bool) (err error) {
 		for i, srcPath := range c.srcPaths {
 			c.srcPaths[i], err = expandPath(srcPath)
 			if err != nil {
-				return trace.Wrap(err, "error expanding %q", srcPath)
+				return trace.Wrap(err)
 			}
 		}
 	}
@@ -337,7 +337,7 @@ func (c *Config) expandPaths(srcIsRemote, dstIsRemote bool) (err error) {
 	if dstIsRemote {
 		c.dstPath, err = expandPath(c.dstPath)
 		if err != nil {
-			return trace.Wrap(err, "error expanding %q", c.dstPath)
+			return trace.Wrap(err)
 		}
 	}
 
@@ -358,7 +358,7 @@ func expandPath(pathStr string) (string, error) {
 		return ".", nil
 	}
 	if pfxLen == 1 && len(pathStr) > 1 {
-		return "", trace.BadParameter("expanding remote ~user paths is not supported, specify an absolute path instead")
+		return "", trace.BadParameter("expanding remote ~user paths is not supported, specify an absolute path instead of %q", pathStr)
 	}
 
 	// if an SFTP path is not absolute, it is assumed to start at the user's