While troubleshooting an email issue I used the old telnet to port 25, and was sending to several unrelated gmail addresses and it failed. I then tested the same at another GW 2012 SP2 site and it failed.
I have tried using Putty and telnet. Telnet was even tried from Windows and Linux. Normal GW client email sends OK, as does some backup software that uses GWIA as the SMTP relay, just not from telnet. Does anyone have any ideas why this is the case?

TELNET TRANSCRIPT:

220 mail.ef.com.au Ready
helo
250 mail.ef.com.au Ok
mail from:test@ef.com.au
250 Ok
rcpt to:me@gmail.com
250 Ok
data
354 Enter mail, end with "." on a line by itself

hi there at 1741
.
250 Ok
. <--------- Here is where I expect to see a "Transferred message"
500 Syntax error
.
500 Syntax error
.
500 Syntax error
.
500 Syntax error
.
500 Syntax error


GWIA LOG showing the error

17:40:19 F3C8 DMN: MSG 113639 Accepted connection: [192.168.0.11] (ef5.ef.corp)
17:40:40 F3C8 DMN: MSG 113639 Receiving file: /gwsystem/efgwia2/wpgate/GWIA2/receive/811f5325.032
17:41:17 F3C0 MSG 113639 Processing inbound message: /gwsystem/efgwia2/wpgate/GWIA2/receive/811f5325.032
17:41:17 F3C0 MSG 113639 Sender: test@ef.com.au
17:41:17 F3C0 MSG 113639 Recipient: me@gmail.com
17:41:17 F3C0 DoCharSetDetection: Character Set: ISO-8859-1, Confidence = 98
17:41:17 F3C0 MSG 113639 Converting message to SMTP: /gwsystem/efgwia2/wpgate/GWIA2/send/x235f13d.008
17:41:17 F3C0 MSG 113639 Queuing message to daemon: /gwsystem/efgwia2/wpgate/GWIA2/send/s235f13d.008
17:41:17 F3C0 Recipient: me@gmail.com
17:41:17 F3D0 DMN: MSG 113639 Sending file: /gwsystem/efgwia2/wpgate/GWIA2/send/p235f13d.008
17:41:17 F3D0 NgwResQuery(gmail.com, 1, 15)
17:41:17 F3D0 Querying server (# 1) address = 192.168.0.2
17:41:17 F3D0 HEADER:
17:41:17 F3D0 opcode = QUERY, id = 54, rcode = NOERROR, flags: qr rd ra
17:41:17 F3D0 query = 1, answer = 5, authority = 0, additional = 1
17:41:17 F3D0
17:41:17 F3D0 QUESTIONS:
17:41:17 F3D0 gmail.com, type = MX, class = IN
17:41:17 F3D0
17:41:17 F3D0 ANSWERS:
17:41:17 F3D0 gmail.com
17:41:17 F3D0 type = MX, class = IN, ttl = 1 hour 9 mins 50 secs, dlen = 25
17:41:17 F3D0 preference = 10, name = aspmx2.googlemail.com
17:41:17 F3D0 gmail.com
17:41:17 F3D0 type = MX, class = IN, ttl = 1 hour 9 mins 50 secs, dlen = 11
17:41:17 F3D0 preference = 10, name = aspmx3.googlemail.com
17:41:17 F3D0 gmail.com
17:41:17 F3D0 type = MX, class = IN, ttl = 1 hour 9 mins 50 secs, dlen = 19
17:41:17 F3D0 preference = 1, name = aspmx.l.google.com
17:41:17 F3D0 gmail.com
17:41:17 F3D0 type = MX, class = IN, ttl = 1 hour 9 mins 50 secs, dlen = 9
17:41:17 F3D0 preference = 5, name = alt1.aspmx.l.google.com
17:41:17 F3D0 gmail.com
17:41:17 F3D0 type = MX, class = IN, ttl = 1 hour 9 mins 50 secs, dlen = 9
17:41:17 F3D0 preference = 5, name = alt2.aspmx.l.google.com
17:41:17 F3D0
17:41:17 F3D0 ADDITIONAL RECORDS:
17:41:17 F3D0 aspmx.l.google.com
17:41:17 F3D0 type = A, class = IN, ttl = 3 mins 3 secs, dlen = 4
17:41:17 F3D0 internet address = 173.194.79.26
17:41:17 F3D0
17:41:17 F3D0 DMN: MSG 113639 Attempting to connect to aspmx.l.google.com
17:41:18 F3D0 DMN: MSG 113639 Connected to [173.194.79.26] (aspmx.l.google.com)
17:41:19 F3D0 DMN: MSG 113639 Send Failure: 550 5.7.1 RFC 2822 specifications for more information. e5si5113815pba.357 - gsmtp
17:41:19 F3D0 DMN: MSG 113639 SMTP session ended: [173.194.79.26] (aspmx.l.google.com)
17:41:27 F476 MSG 113639 Analyzing result file: /gwsystem/efgwia2/wpgate/GWIA2/result/r235f13d.008
17:41:27 F476 MSG 113639 Command: gmail.com
17:41:27 F476 MSG 113639 Response: 220 mx.google.com ESMTP e5si5113815pba.357 - gsmtp
17:41:27 F476 MSG 113639 Command: EHLO mail.ef.com.au
17:41:27 F476 MSG 113639 Response: 250 ok
17:41:27 F476 MSG 113639 Command: MAIL FROM:<test@ef.com.au>
17:41:27 F476 MSG 113639 Response: 250 2.1.0 OK e5si5113815pba.357 - gsmtp
17:41:27 F476 MSG 113639 Command: RCPT TO:<me@gmail.com>
17:41:27 F476 MSG 113639 Response: 250 2.1.5 OK e5si5113815pba.357 - gsmtp
17:41:27 F476 MSG 113639 Command: DATA
17:41:27 F476 MSG 113639 Response: 354 Go ahead e5si5113815pba.357 - gsmtp
17:41:27 F476 MSG 113639 Detected error on SMTP command
17:41:27 F476 MSG 113639 Command: Data...
17:41:27 F476 MSG 113639 Response: 550 5.7.1 RFC 2822 specifications for more information. e5si5113815pba.357 - gsmtp

17:41:27 F476 Building undeliverable message

Can any one else confirm if they can telnet successfully through their GW 2012 SP2 GWIA to a GMAIL address

Thanks
Gordon