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I am getting bounce back emails, when sending out emails

I am running exchange 2016 internally in my organization, on-prem.
I did have 2 IPs for our RDNS, but got that corrected yesterday, and I also updated our SPF record as well. Everything seems to be configured fine, and we're not listed as a spammer either, so I'm not sure why people are still having issues sending external email, here's a few examples.

Diagnostic information for administrators:
Generating server: mail.mydomain.org
support@vandyke.com
mx1.swcp.com
Remote Server returned '554 5.0.0 <mx1.swcp.com #5.0.0 smtp; 550 5.7.1 <Dxxxxxx@mydomain.org>... fail>'

Diagnostic information for administrators:
Generating server: mail.mydomain.org
christina.kopp@t-online.de
Remote Server returned '554 5.0.0 < #5.0.0>'
Original message headers:

SOLUTION

Saif Shaikh

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Dan

ASKER

thanks everything looks fine there, what's next?

SOLUTION

Mohammed Khawaja

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Dan

ASKER

So I need to make those changes on my exchange server? How come it worked all this time?
Can you point me in the right direction, are we talking about virtual directories, send connectors, etc...?

Dan

ASKER

Just checked the send connector and it's using my DNS name, no IPs listed, seems fine to me.

Dan

ASKER

Here's another one where an internal user tried to send an email to the address at hiroshimadaggett.com, but faiiled.

Diagnostic information for administrators:
Generating server: mail.mydomain.org
jdaggett@hiroshimadaggett.com
d160049b.ess.barracudanetworks.com
Remote Server returned '554 5.0.0 <d160049b.ess.barracudanetworks.com #5.0.0 smtp; 550 permanent failure for one or more recipients (jdaggett@hiroshimadaggett.com:blocked)>'

Dan

ASKER

I went to https://testconnectivity.microsoft.com/ and entered my external IP address and everything was good, all green checkmarks.

kenfcamp

Did you perform a lookup at BarracudaCentral? -- https://www.barracudacentral.org/lookups

Diagnostic information for administrators:

Could you provide the "full" diagnostic information report?
It may provide information that we don't have.

Feel free to redact IP and email information (I would)

Dan

ASKER

when going to https://www.barracudacentral.org/lookups , I checked the IP addresses and DNS name, and everything was good, clear.

Here's the full report:

Delivery has failed to these recipients or groups:
jdaggett@hiroshimadaggett.com
A problem occurred while delivering your message to this email address. Try sending your message again.
If the problem continues, please contact your email admin.
The following organization rejected your message: d160049a.ess.barracudanetworks.com.

Diagnostic information for administrators:
Generating server: mail.mydomain.org
jdaggett@hiroshimadaggett.com
d160049a.ess.barracudanetworks.com
Remote Server returned '554 5.0.0 <d160049a.ess.barracudanetworks.com #5.0.0 smtp; 550 permanent
failure for one or more recipients (jdaggett@hiroshimadaggett.com:blocked)>'
Original message headers:
Return-Path: <dxxxxxxx@mydomain.org>
Received: from [192.168.100.110] (port=59717 helo=mail.mydomain.org)
by mail.mydomain.org with esmtps (TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128)
(Exim 4.91)
(envelope-from <dxxxxxxx@mydomain.org>)
id 1lEz6v-0000J6-FK
for jdaggett@hiroshimadaggett.com; Wed, 24 Feb 2021 10:42:09 -0800
Received: from exchange.mydomain.org (192.168.100.110) by
exchange.mydomain.org (192.168.100.110) with Microsoft SMTP Server
(version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256) id
15.1.1979.3; Wed, 24 Feb 2021 10:42:09 -0800
Received: from exchange.mydomain.org ([fe80::6495:5cbc:cd5a:cb8c]) by
exchange.mydomain.org ([fe80::6495:5cbc:cd5a:cb8c%5]) with mapi id
15.01.1979.006; Wed, 24 Feb 2021 10:42:09 -0800
From: Dan Lastname <dxxxxxxx@mydomain.org>
To: "jdaggett@hiroshimadaggett.com" <jdaggett@hiroshimadaggett.com>
Subject: test email
Thread-Topic: test email
Thread-Index: AdcK3LeIpzsSi/hzTgG9405xUEFkog==
Date: Wed, 24 Feb 2021 18:42:08 +0000
Message-ID: <a9c02bde1b7b4867b659549f4fb91ac7@mydomain.org>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
x-originating-ip: [10.242.2.4]
Content-Type: multipart/alternative;
boundary="_000_a9c02bde1b7b4867b659549f4fb91ac7mydomainorg_"
MIME-Version: 1.0
X-Sophos-OBS: success
X-CTCH-PVer: 0000001
X-CTCH-Spam: Unknown
X-CTCH-VOD: Unknown
X-CTCH-Flags: 0
X-CTCH-RefID: str=0001.0A09020B.60369E01.0023,ss=1,re=0.000,recu=0.000,reip=0.000,cl=1,cld=1,fgs=0
X-CTCH-Score: 0.000
X-CTCH-ScoreCust: 0.000
X-CTCH-Rules:

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kenfcamp

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Dan

ASKER

I figured out the problem, my firewall was using masquerading and using the external IP of my firewall.
I added the new IP as the masq IP and now it's working.

Thanks everyone for your input.

kenfcamp

Yea, I thought that something like that might be happening.

Glad you got it figured out