Don't know how to add an attachment - maybe not enabled but wireshark lets you export captures as text. The things to look at are frame 4 is the Client Hello (full decode goes through all supported encryption options from the connection attempt of DVC to the server), frame 5 is the ACK from the server and immediately frame 6 is the gmail server sending a TLS fatal message that the protocol isn't acceptable. The rest is just the closing of the TCP connection. This is with the authentication (which never gets that far), SSL checked and going to port 465 for the gmail connection. These settings used to work but gmail locked down some things recently excluding more "insecure" protocols. Trying other options (different ports, no selection of SSL etc.) results in different errors but are more of the type that a protocol is expected but not being used. This is the most meaningful capture where the protocols are correct, gmail just isn't going to accept any of the offered security options. I'd be glad to send the pcap file if you can tell me how.
No. Time Source Destination Protocol Length Info
1 0.000000 10.0.0.3 gmail-smtp-msa.l.google.com TCP 66 60459 → 465 [SYN] Seq=0 Win=8192 Len=0 MSS=1460 WS=256 SACK_PERM=1
Frame 1: 66 bytes on wire (528 bits), 66 bytes captured (528 bits) on interface 0
Ethernet II, Src: AsustekC_09:98:e3 (00:24:8c:09:98:e3), Dst: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e)
Internet Protocol Version 4, Src: 10.0.0.3 (10.0.0.3), Dst: gmail-smtp-msa.l.google.com (74.125.21.108)
Transmission Control Protocol, Src Port: 60459 (60459), Dst Port: 465 (465), Seq: 0, Len: 0
Source Port: 60459
Destination Port: 465
[Stream index: 0]
[TCP Segment Len: 0]
Sequence number: 0 (relative sequence number)
Acknowledgment number: 0
Header Length: 32 bytes
Flags: 0x002 (SYN)
Window size value: 8192
[Calculated window size: 8192]
Checksum: 0x6a12 [validation disabled]
Urgent pointer: 0
Options: (12 bytes), Maximum segment size, No-Operation (NOP), Window scale, No-Operation (NOP), No-Operation (NOP), SACK permitted
No. Time Source Destination Protocol Length Info
2 0.021330 gmail-smtp-msa.l.google.com 10.0.0.3 TCP 66 465 → 60459 [SYN, ACK] Seq=0 Ack=1 Win=43152 Len=0 MSS=1392 SACK_PERM=1 WS=128
Frame 2: 66 bytes on wire (528 bits), 66 bytes captured (528 bits) on interface 0
Ethernet II, Src: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e), Dst: AsustekC_09:98:e3 (00:24:8c:09:98:e3)
Internet Protocol Version 4, Src: gmail-smtp-msa.l.google.com (74.125.21.108), Dst: 10.0.0.3 (10.0.0.3)
Transmission Control Protocol, Src Port: 465 (465), Dst Port: 60459 (60459), Seq: 0, Ack: 1, Len: 0
Source Port: 465
Destination Port: 60459
[Stream index: 0]
[TCP Segment Len: 0]
Sequence number: 0 (relative sequence number)
Acknowledgment number: 1 (relative ack number)
Header Length: 32 bytes
Flags: 0x012 (SYN, ACK)
Window size value: 43152
[Calculated window size: 43152]
Checksum: 0x19e4 [validation disabled]
Urgent pointer: 0
Options: (12 bytes), Maximum segment size, No-Operation (NOP), No-Operation (NOP), SACK permitted, No-Operation (NOP), Window scale
[SEQ/ACK analysis]
No. Time Source Destination Protocol Length Info
3 0.021410 10.0.0.3 gmail-smtp-msa.l.google.com TCP 54 60459 → 465 [ACK] Seq=1 Ack=1 Win=66816 Len=0
Frame 3: 54 bytes on wire (432 bits), 54 bytes captured (432 bits) on interface 0
Ethernet II, Src: AsustekC_09:98:e3 (00:24:8c:09:98:e3), Dst: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e)
Internet Protocol Version 4, Src: 10.0.0.3 (10.0.0.3), Dst: gmail-smtp-msa.l.google.com (74.125.21.108)
Transmission Control Protocol, Src Port: 60459 (60459), Dst Port: 465 (465), Seq: 1, Ack: 1, Len: 0
Source Port: 60459
Destination Port: 465
[Stream index: 0]
[TCP Segment Len: 0]
Sequence number: 1 (relative sequence number)
Acknowledgment number: 1 (relative ack number)
Header Length: 20 bytes
Flags: 0x010 (ACK)
Window size value: 261
[Calculated window size: 66816]
[Window size scaling factor: 256]
Checksum: 0x6a06 [validation disabled]
Urgent pointer: 0
[SEQ/ACK analysis]
No. Time Source Destination Protocol Length Info
4 0.021456 10.0.0.3 gmail-smtp-msa.l.google.com TLSv1 194 Client Hello
Frame 4: 194 bytes on wire (1552 bits), 194 bytes captured (1552 bits) on interface 0
Ethernet II, Src: AsustekC_09:98:e3 (00:24:8c:09:98:e3), Dst: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e)
Internet Protocol Version 4, Src: 10.0.0.3 (10.0.0.3), Dst: gmail-smtp-msa.l.google.com (74.125.21.108)
Transmission Control Protocol, Src Port: 60459 (60459), Dst Port: 465 (465), Seq: 1, Ack: 1, Len: 140
Source Port: 60459
Destination Port: 465
[Stream index: 0]
[TCP Segment Len: 140]
Sequence number: 1 (relative sequence number)
[Next sequence number: 141 (relative sequence number)]
Acknowledgment number: 1 (relative ack number)
Header Length: 20 bytes
Flags: 0x018 (PSH, ACK)
Window size value: 261
[Calculated window size: 66816]
[Window size scaling factor: 256]
Checksum: 0x6a92 [validation disabled]
Urgent pointer: 0
[SEQ/ACK analysis]
Secure Sockets Layer
TLSv1 Record Layer: Handshake Protocol: Client Hello
Content Type: Handshake (22)
Version: SSL 3.0 (0x0300)
Length: 135
Handshake Protocol: Client Hello
No. Time Source Destination Protocol Length Info
5 0.041829 gmail-smtp-msa.l.google.com 10.0.0.3 TCP 60 465 → 60459 [ACK] Seq=1 Ack=141 Win=44288 Len=0
Frame 5: 60 bytes on wire (480 bits), 60 bytes captured (480 bits) on interface 0
Ethernet II, Src: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e), Dst: AsustekC_09:98:e3 (00:24:8c:09:98:e3)
Internet Protocol Version 4, Src: gmail-smtp-msa.l.google.com (74.125.21.108), Dst: 10.0.0.3 (10.0.0.3)
Transmission Control Protocol, Src Port: 465 (465), Dst Port: 60459 (60459), Seq: 1, Ack: 141, Len: 0
Source Port: 465
Destination Port: 60459
[Stream index: 0]
[TCP Segment Len: 0]
Sequence number: 1 (relative sequence number)
Acknowledgment number: 141 (relative ack number)
Header Length: 20 bytes
Flags: 0x010 (ACK)
Window size value: 346
[Calculated window size: 44288]
[Window size scaling factor: 128]
Checksum: 0x011d [validation disabled]
Urgent pointer: 0
[SEQ/ACK analysis]
No. Time Source Destination Protocol Length Info
6 0.041832 gmail-smtp-msa.l.google.com 10.0.0.3 TLSv1 61 Alert (Level: Fatal, Description: Protocol Version)
Frame 6: 61 bytes on wire (488 bits), 61 bytes captured (488 bits) on interface 0
Ethernet II, Src: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e), Dst: AsustekC_09:98:e3 (00:24:8c:09:98:e3)
Internet Protocol Version 4, Src: gmail-smtp-msa.l.google.com (74.125.21.108), Dst: 10.0.0.3 (10.0.0.3)
Transmission Control Protocol, Src Port: 465 (465), Dst Port: 60459 (60459), Seq: 1, Ack: 141, Len: 7
Source Port: 465
Destination Port: 60459
[Stream index: 0]
[TCP Segment Len: 7]
Sequence number: 1 (relative sequence number)
[Next sequence number: 8 (relative sequence number)]
Acknowledgment number: 141 (relative ack number)
Header Length: 20 bytes
Flags: 0x018 (PSH, ACK)
Window size value: 346
[Calculated window size: 44288]
[Window size scaling factor: 128]
Checksum: 0xa308 [validation disabled]
Urgent pointer: 0
[SEQ/ACK analysis]
Secure Sockets Layer
TLSv1 Record Layer: Alert (Level: Fatal, Description: Protocol Version)
Content Type: Alert (21)
Version: TLS 1.0 (0x0301)
Length: 2
Alert Message
Level: Fatal (2)
Description: Protocol Version (70)
No. Time Source Destination Protocol Length Info
7 0.041832 gmail-smtp-msa.l.google.com 10.0.0.3 TCP 60 465 → 60459 [FIN, ACK] Seq=8 Ack=141 Win=44288 Len=0
Frame 7: 60 bytes on wire (480 bits), 60 bytes captured (480 bits) on interface 0
Ethernet II, Src: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e), Dst: AsustekC_09:98:e3 (00:24:8c:09:98:e3)
Internet Protocol Version 4, Src: gmail-smtp-msa.l.google.com (74.125.21.108), Dst: 10.0.0.3 (10.0.0.3)
Transmission Control Protocol, Src Port: 465 (465), Dst Port: 60459 (60459), Seq: 8, Ack: 141, Len: 0
Source Port: 465
Destination Port: 60459
[Stream index: 0]
[TCP Segment Len: 0]
Sequence number: 8 (relative sequence number)
Acknowledgment number: 141 (relative ack number)
Header Length: 20 bytes
Flags: 0x011 (FIN, ACK)
Window size value: 346
[Calculated window size: 44288]
[Window size scaling factor: 128]
Checksum: 0x0115 [validation disabled]
Urgent pointer: 0
No. Time Source Destination Protocol Length Info
8 0.041981 10.0.0.3 gmail-smtp-msa.l.google.com TCP 54 60459 → 465 [ACK] Seq=141 Ack=9 Win=66560 Len=0
Frame 8: 54 bytes on wire (432 bits), 54 bytes captured (432 bits) on interface 0
Ethernet II, Src: AsustekC_09:98:e3 (00:24:8c:09:98:e3), Dst: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e)
Internet Protocol Version 4, Src: 10.0.0.3 (10.0.0.3), Dst: gmail-smtp-msa.l.google.com (74.125.21.108)
Transmission Control Protocol, Src Port: 60459 (60459), Dst Port: 465 (465), Seq: 141, Ack: 9, Len: 0
Source Port: 60459
Destination Port: 465
[Stream index: 0]
[TCP Segment Len: 0]
Sequence number: 141 (relative sequence number)
Acknowledgment number: 9 (relative ack number)
Header Length: 20 bytes
Flags: 0x010 (ACK)
Window size value: 260
[Calculated window size: 66560]
[Window size scaling factor: 256]
Checksum: 0x6a06 [validation disabled]
Urgent pointer: 0
[SEQ/ACK analysis]
No. Time Source Destination Protocol Length Info
9 0.042033 10.0.0.3 gmail-smtp-msa.l.google.com TLSv1 61 Alert (Level: Fatal, Description: Handshake Failure)
Frame 9: 61 bytes on wire (488 bits), 61 bytes captured (488 bits) on interface 0
Ethernet II, Src: AsustekC_09:98:e3 (00:24:8c:09:98:e3), Dst: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e)
Internet Protocol Version 4, Src: 10.0.0.3 (10.0.0.3), Dst: gmail-smtp-msa.l.google.com (74.125.21.108)
Transmission Control Protocol, Src Port: 60459 (60459), Dst Port: 465 (465), Seq: 141, Ack: 9, Len: 7
Source Port: 60459
Destination Port: 465
[Stream index: 0]
[TCP Segment Len: 7]
Sequence number: 141 (relative sequence number)
[Next sequence number: 148 (relative sequence number)]
Acknowledgment number: 9 (relative ack number)
Header Length: 20 bytes
Flags: 0x018 (PSH, ACK)
Window size value: 260
[Calculated window size: 66560]
[Window size scaling factor: 256]
Checksum: 0x6a0d [validation disabled]
Urgent pointer: 0
[SEQ/ACK analysis]
Secure Sockets Layer
TLSv1 Record Layer: Alert (Level: Fatal, Description: Handshake Failure)
Content Type: Alert (21)
Version: TLS 1.0 (0x0301)
Length: 2
Alert Message
Level: Fatal (2)
Description: Handshake Failure (40)
No. Time Source Destination Protocol Length Info
10 0.042158 10.0.0.3 gmail-smtp-msa.l.google.com TCP 54 60459 → 465 [RST, ACK] Seq=148 Ack=9 Win=0 Len=0
Frame 10: 54 bytes on wire (432 bits), 54 bytes captured (432 bits) on interface 0
Ethernet II, Src: AsustekC_09:98:e3 (00:24:8c:09:98:e3), Dst: Netgear_b6:f7:2e (50:6a:03:b6:f7:2e)
Internet Protocol Version 4, Src: 10.0.0.3 (10.0.0.3), Dst: gmail-smtp-msa.l.google.com (74.125.21.108)
Transmission Control Protocol, Src Port: 60459 (60459), Dst Port: 465 (465), Seq: 148, Ack: 9, Len: 0
Source Port: 60459
Destination Port: 465
[Stream index: 0]
[TCP Segment Len: 0]
Sequence number: 148 (relative sequence number)
Acknowledgment number: 9 (relative ack number)
Header Length: 20 bytes
Flags: 0x014 (RST, ACK)
Window size value: 0
[Calculated window size: 0]
[Window size scaling factor: 256]
Checksum: 0x6a06 [validation disabled]
Urgent pointer: 0