After trying this for a while and watching the tethereal output i have noticed something: a Successful upload: ======= 37.406692 196.41.186.226 -> 192.168.0.220 FTP Request: PASV 37.406913 192.168.0.220 -> 196.41.186.226 FTP Response: 227 Entering Passive Mode (192,168,0,220,137,132). 37.455288 196.41.186.226 -> 192.168.0.220 TCP ms-sql-s > 35204 [SYN] Seq=0 Ack=0 Win=16384 Len=0 MSS=1360 37.455310 192.168.0.220 -> 196.41.186.226 TCP 35204 > ms-sql-s [SYN, ACK] Seq=0 Ack=1 Win=5840 Len=0 MSS=1460 37.465549 196.41.186.226 -> 192.168.0.220 FTP Request: STOR LANDING_17.jpg 37.490491 196.41.186.226 -> 192.168.0.220 TCP ms-sql-s > 35204 [ACK] Seq=1 Ack=1 Win=17680 Len=0 37.490618 192.168.0.220 -> 196.41.186.226 FTP Response: 150 Opening BINARY mode data connection for LANDING_17.jpg 37.664991 196.41.186.226 -> 192.168.0.220 FTP-DATA FTP Data: 1360 bytes 37.665008 192.168.0.220 -> 196.41.186.226 TCP 35204 > ms-sql-s [ACK] Seq=1 Ack=1361 Win=8160 Len=0 37.670007 196.41.186.226 -> 192.168.0.220 FTP-DATA FTP Data: 305 bytes 37.670020 192.168.0.220 -> 196.41.186.226 TCP 35204 > ms-sql-s [ACK] Seq=1 Ack=1666 Win=8160 Len=0 37.675092 196.41.186.226 -> 192.168.0.220 TCP ms-sql-s > 35204 [FIN, ACK] Seq=1666 Ack=1 Win=17680 Len=0 37.675222 192.168.0.220 -> 196.41.186.226 TCP 35204 > ms-sql-s [FIN, ACK] Seq=1 Ack=1667 Win=8160 Len=0 37.675713 192.168.0.220 -> 196.41.186.226 FTP Response: 226 Transfer complete. ======= A Unsuccessful upload: ======= 37.921391 196.41.186.226 -> 192.168.0.220 FTP Request: PASV 37.921611 192.168.0.220 -> 196.41.186.226 FTP Response: 227 Entering Passive Mode (192,168,0,220,137,133). 37.961478 196.41.186.226 -> 192.168.0.220 TCP ms-sql-m > 35205 [SYN] Seq=0 Ack=0 Win=16384 Len=0 MSS=1360 37.961501 192.168.0.220 -> 196.41.186.226 TCP 35205 > ms-sql-m [SYN, ACK] Seq=0 Ack=1 Win=5840 Len=0 MSS=1460 37.967146 196.41.186.226 -> 192.168.0.220 FTP Request: STOR LANDING_18.jpg 37.982217 196.41.186.226 -> 192.168.0.220 TCP ms-sql-m > 35205 [ACK] Seq=1 Ack=1 Win=17680 Len=0 37.982349 192.168.0.220 -> 196.41.186.226 FTP Response: 150 Opening BINARY mode data connection for LANDING_18.jpg 38.189397 196.41.186.226 -> 192.168.0.220 TCP 1407 > ftp [ACK] Seq=2306 Ack=6579 Win=16535 Len=0 38.309509 192.168.0.220 -> 196.41.186.226 FTP [TCP Out-Of-Order] Response: 38.493193 196.41.186.226 -> 192.168.0.220 TCP 1407 > ftp [ACK] Seq=2306 Ack=6581 Win=16533 Len=0 53.301514 196.41.186.226 -> 192.168.0.220 TCP 1407 > ftp [FIN, ACK] Seq=2306 Ack=6581 Win=16533 Len=0 ======= If you check the first one, it Opens the BINARY connection and the you have a FTP-DATA command which gives it the file size in the 2nd one, it Opens the Binary connection and there is no FTP-DATA issued?