Issue with email from outlook
Question asked by Keith Bromwich - 6/17/2017 at 4:16 PM
I have a client that uses a vpn for their internet connection. When connected to the VPN and they send an email from outlook, the message gets marked as spam.
It is the smartermail server that is registering the email as spam and rejecting the message.
I have tried whitelisting the IP of the VPN and selecting to bypass spam filtering but it does not seem to work.
What am i doing wrong to fix this issue?
message returned from smartermail
Could not deliver message to the following recipient(s):

Failed Recipient: xxx@an-email.com
Reason: This message cannot be delivered as it was marked as spam.

-- The header and top 20 lines of the message follows --

Received: from xxxxx (209-107-195-188.ipvanish.com []) by smartermailserver.com with SMTP

5 Replies

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Matthew Shepard Replied
You could look into the delivery and smtp logs and that should let you see if it is the overall spam settings or some content filtering kicking in. Is it just one user or multiple users? You can try to add their e-mails to the domain trusted senders list, this should bypass spam filtering. 
Keith Bromwich Replied
There is nothing in the logs. This is a client that has their domain hosted on the server. They are sending an email to another person. When the send through outlook, which goes through the server to send the email, the server blocks the email and says it is spam. The server is set to block out going spam.
The vpn ip range has been listed on the white list and also to bypass spam filtering but the server is still filtering out the message and bouncing it back to outlook.

example from smtp logs
[2017.06.20] 12:10:03 [][33876674] rsp: 220 mailserver.com
[2017.06.20] 12:10:03 [][33876674] connected at 20/06/2017 12:10:03 PM
[2017.06.20] 12:10:03 [][33876674] IP in whitelist
[2017.06.20] 12:10:03 [][33876674] cmd: EHLO Nerdster
[2017.06.20] 12:10:03 [][33876674] rsp: 250-mailserver.com Hello []250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250-8BITMIME250 OK
[2017.06.20] 12:10:03 [][33876674] cmd: AUTH LOGIN
[2017.06.20] 12:10:03 [][33876674] rsp: 334 VXNlcm5hbWU6gggg
[2017.06.20] 12:10:03 [][33876674] Authenticating as user@somedomain.com
[2017.06.20] 12:10:03 [][33876674] rsp: 334 UGFzc3dvcmQ6ddd3fffr
[2017.06.20] 12:10:03 [][33876674] rsp: 235 Authentication successful
[2017.06.20] 12:10:03 [][33876674] Authenticated as user@somedomain.com
[2017.06.20] 12:10:03 [][33876674] cmd: MAIL FROM: <user@somedomain.com>
[2017.06.20] 12:10:03 [][33876674] rsp: 250 OK <user@somedomain.com> Sender ok
[2017.06.20] 12:10:03 [][33876674] cmd: RCPT TO: <recipient@anotherdomain.com>
[2017.06.20] 12:10:03 [][33876674] rsp: 250 OK <recipient@anotherdomain.com> Recipient ok
[2017.06.20] 12:10:03 [][33876674] cmd: DATA
[2017.06.20] 12:10:04 [][33876674] rsp: 354 Start mail input; end with <CRLF>.<CRLF>
[2017.06.20] 12:10:04 [][33876674] rsp: 250 OK
[2017.06.20] 12:10:04 [][33876674] Data transfer succeeded, writing mail to 152239427.eml
[2017.06.20] 12:10:07 [][33876674] cmd: QUIT
[2017.06.20] 12:10:07 [][33876674] rsp: 221 Service closing transmission channel
[2017.06.20] 12:10:07 [][33876674] disconnected at 20/06/2017 12:10:07 PM

This is all that is in the logs that i can find. There are no other records. i have set it show all related traffic

The email does not leave the server and it is rejected as spam. there are no spam records in the log
Randy Armbrecht Replied
just to verify - you have the IP address whitelisted?
Keith Bromwich Replied
yes the ip is in the whitelist. if you look at the log above you will also see in the log the following line
[2017.06.20] 12:10:03 [][33876674] IP in whitelist

Matthew Shepard Replied
How do you know it is being rejected as spam? Is it possible there is some sort of routing issue instead? Are you able to see it in the spool if you watch the spool right around when he sends the e-mail? If he logs into the webmail interface does it show up as a sent e-mail in his sent folder? Are you using an outgoing or incoming mail gateway server?

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