Delivery has failed to these recipients or groups:

I keep getting these Undeliverable: emails.

1. The think is the emails are being undelivered to my email address.
2. The email that's said to be undelivered was also delivered to my email address without issues.

Diagnostic information for administrators:

Generating server: MAIL.domain.local
Receiving server: MAIL.domain.local
Total retry attempts: 192

user@domain.com
11/1/2017 4:02:51 AM - Server at MAIL.domain.local returned '550 5.4.300 Message expired'
Original message headers:

Resent-From: <user@domain.com>
Received: from MAIL.domain.local (192.168.94.102) by MAIL.domain.local
 (192.168.94.102) with Microsoft SMTP Server (version=TLS1_2,
 cipher=TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P256) id 15.1.1034.26; Mon, 30
 Oct 2017 00:10:47 -0400
Received: from gears217-15.expediamail.com (135.84.217.15) by MAIL.domain.local
 (192.168.94.102) with Microsoft SMTP Server id 15.1.1034.26 via Frontend
 Transport; Mon, 30 Oct 2017 00:10:46 -0400
Date: Mon, 30 Oct 2017 00:10:13 -0400
From: Expedia.com <Expedia@expediamail.com>
Reply-To: <Expedia@expediamail.com>
To: <user@domain.com>
Message-ID: <1329376759.235612790.1509336613970.JavaMail.root@mta0201.messagegears.net>
Subject: Review your recent stay at The Parc Hotel
MIME-Version: 1.0
Content-Type: multipart/mixed;
      boundary="----=_Part_235612787_130711495.1509336613969"
X-WatchGuard-Spam-ID: str=0001.0A020206.59F6A627.0062:SCGSTAT2190527,ss=1,re=0.000,recu=0.000,reip=0.000,cl=1,cld=1,fgs=1024
X-WatchGuard-Spam-Score: 0, clean; 0, virus threat unknown
X-WatchGuard-Mail-Client-IP: 135.84.217.15
X-WatchGuard-Mail-From: 382642165000000014202-c17303-73f79bc10ace438ab006fb9f770cbbc7@mg.expediamail.com
Return-Path: 382642165000000014202-c17303-73f79bc10ace438ab006fb9f770cbbc7@mg.expediamail.com
sf1eldsAsked:
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KimputerCommented:
So to be clear, you always get these Undeliverable message for ALL your emals? And you get ALL those original emails a few hours before already in your mailbox?
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sf1eldsAuthor Commented:
It does not happen for all the emails.
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KimputerCommented:
For those that do happen, you receive the original email already a few hours before the undeliverable message?
0
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sf1eldsAuthor Commented:
Correct
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Hemil AquinoNetwork EngineerCommented:
Can you check your email queue and tell me what you see there?
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Hemil AquinoNetwork EngineerCommented:
Go to exchange toolbox> queue viewer on windows
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sf1eldsAuthor Commented:
Screen Shot
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Muhammad AsifSenior Solutions ArchitectCommented:
If you have configured any smarthost and firewall then please make sure that these appliances are configured properly.
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Hemil AquinoNetwork EngineerCommented:
Sorry for the delay, did you got it fixed. I've been quite busy.
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sf1eldsAuthor Commented:
Not yet. I started a new tread because it got worst. Other users having the issue as well.
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Hemil AquinoNetwork EngineerCommented:
Dns issue try binding the dns server.

Internal: your dns server.
External your public dns server
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sf1eldsAuthor Commented:
Hemil Aquino: Can you explain further?
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Hemil AquinoNetwork EngineerCommented:
Go to ECP/ server, name of the server double click, dns and change the binding.
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sf1eldsAuthor Commented:
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sf1eldsAuthor Commented:
DNS lookups
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sf1eldsAuthor Commented:
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Hemil AquinoNetwork EngineerCommented:
Yes, change the internal and external with what I've mentioned above. IP address of your dns server for your internal.

Public dns server for your external.

Don't use all the interfaces.
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Hemil AquinoNetwork EngineerCommented:
Any luck?
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sf1eldsAuthor Commented:
Will check now. Was out of office.
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sf1eldsAuthor Commented:
Well I just sent an email to two address I had problems with. I don't see an NDR in my inbox. I asked them to reply if they see my email.

No replies yet.
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Hemil AquinoNetwork EngineerCommented:
Try using an outside account, like gmail, yahoo etc..
And test it. So how it goes.!
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sf1eldsAuthor Commented:
That's the thing. I didn't have an issue sending to my external addresses.
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Hemil AquinoNetwork EngineerCommented:
How does your MX records looks like?
It's your ip address clean?
Are you using static or dynamic ip address?
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sf1eldsAuthor Commented:
IP address is clean
Static

Tried sending to a hotmail account and that worked.
Tried sending to a outlook account and that did not work.

It was not received.
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Hemil AquinoNetwork EngineerCommented:
when you say Outlook account you mean office365.com? outlook online account?
Do you have any email in your draft?
Can you check the queue and see what's in there?
Did you receive any bounce back?
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sf1eldsAuthor Commented:
user@outlook.com
No email in draft
nothing unusual in queue
No bounce back
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Hemil AquinoNetwork EngineerCommented:
Did you tell the person to look into his spam emails?
sometimes email goes to spam folders.. if you haven't gotten any bounce back it means everything went well with the other end.
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sf1eldsAuthor Commented:
Not in spam for one user.

The other user unavailable at this moment.
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Hemil AquinoNetwork EngineerCommented:
Do you know if the person unintentionally placed your email as Spam and the email got blocked? I seen t his happen couple of days ago and I was going nut looking everywhere.
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sf1eldsAuthor Commented:
Well I don't know that.
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sf1eldsAuthor Commented:
Will have them check
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Hemil AquinoNetwork EngineerCommented:
Those are question you need to ask in order for you to determine what's going on with the recipient.
Now, try this, create an outlook account and test yourself, that way you can determine whether is true or not.
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sf1eldsAuthor Commented:
Ok will do that now.
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