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YMartin

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Exchange 2016 Transport Rules block moderation reject message

We are moderating gmail with a whitelist exception due to the huge volume of spoofing attempts coming from gmail.  We would like a way to reject messages without a rejection notice being sent.

I have attempted to create another transport rule based on the subject pattern '^Rejected:' but it does not catch the rejection email despite the subject beginning with "Rejected:".  It seems the Microsoft Exchange Approval Assistant mailbox mailflow does not pass through the transport rules.

I am looking for ways to block the rejection notice on moderated emails going back out to gmail.  Perhaps editing the send permissions on the Microsoft Exchange Approval Assistant mailbox and restricting it to inside the organization?

Any advise would be appreciated.
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Jeffrey Kane - TechSoEasy
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Creating a manual filter against GMail seems like a poor method of handling your email security.   What about the 10,000 other things which you need to protect against?

Modern Email Protection (software or hardware) is able to recognize phishing attempts no matter what domain or email service they are coming from because they have the ability to see data across thousands of servers and billions of email messages.  

The cost of manually moderating the amount of messages you'll receive from GMail will be significantly higher than purchasing proper email protection solution that will deal with all problems, not just this one.

Do you have an email protection solution in place already?  If so, that is where you need to tighten up the settings if too many things are getting through.  If you don't already have a protection solution  focus on getting that done before you do something like you are suggesting above.
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YMartin

ASKER

Thank you Jeffrey,

We are already using a SPAM service which is usually quite effective.  However these Spammers are creating custom gmail accounts and sending fake email messages with no links which are eluding their filters.  The client has requested moderation as all attacks are coming from Gmail.

Obviously I would prefer that the spammers not receive the notification that they have been blocked.
Sorry, I completely misread your question to begin with - so you are wanting to block the NDR's?  

Obviously I would prefer that the spammers not receive the notification that they have been blocked.

Actually, that isn't an obvious thing -- because its not something that even matters.  The NDR goes to a SPOOFED Gmail address, not a real one -- so GMail will blackhole that message.  Even if it was a real one, spammers will never see the NDR because they couldn't care less about them.  

When you send out over 10,000,000 emails a day, you certainly aren't worried if 3,000,000 aren't delivered because you were able to get 7,000,000 into mailboxes.

Do you see what I'm saying about this?  What you are trying to do doesn't need to be done.
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ASKER

I suppose technically it isn't spamming but Phishing.  I tend to group all unwanted mail under the general heading of SPAM.  

It is not a spoofed email address but a spoofed display name.  The email address is valid and someone is  monitoring it as users have received replies.

I still need to block the NDR.
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Avatar of Jeffrey Kane - TechSoEasy
Jeffrey Kane - TechSoEasy
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Thanks.  That sounds like it should work.  I am running into the following:

The operation couldn't be performed because object 'gmail.com' couldn't be found on DC...
You'll need to create a separate send connector for gmail.com to isolate that traffic.
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ASKER

Thanks.  Figured it out.  Need  new-remotedomain first then set-remotedomain works.
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ASKER

Unfortunately this does not work for the moderation reject messages.  I have set properties as shown below.  It does block NDR's but not a moderation rejection message.

DomainName                           : Gmail.com
IsInternal                           : False
TargetDeliveryDomain                 : False
ByteEncoderTypeFor7BitCharsets       : Undefined
CharacterSet                         :
NonMimeCharacterSet                  :
AllowedOOFType                       : None
AutoReplyEnabled                     : True
AutoForwardEnabled                   : True
DeliveryReportEnabled                : False
NDREnabled                           : False
MeetingForwardNotificationEnabled    : False
ContentType                          : MimeHtmlText
DisplaySenderName                    : True
PreferredInternetCodePageForShiftJis : Undefined
RequiredCharsetCoverage              :
TNEFEnabled                          : True
LineWrapSize                         : Unlimited
TrustedMailOutboundEnabled           : False
TrustedMailInboundEnabled            : False
UseSimpleDisplayName                 : False
NDRDiagnosticInfoEnabled             : False
MessageCountThreshold                : 2147483647
AdminDisplayName                     :
ExchangeVersion                      : 0.1 (8.0.535.0)
Name                                 : Gmail
Identity                             : Gmail

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