Problems sending from Outlook 365 to Exchange Server 2003

We had a problem with our Exchange Server 2003 last week and still am not sure we have recovered from it. It started with some of or customers that use Proofpoint. Proofpoint did an upgrade last week that that stopped people that use it from sending to our Exchange Server 2003. The upgrade refused to send to any mail server using RC4 cipher and that is Exchange Server 2003.

Now it looks likes something is going on with Office 365. People using Office 365 for some reason can't seem to send to our Exchange Server 2003. There are no signs of errors on the Exchange Server. They are getting emails from other outside sources. I just sent four users a test from my Outlook 365 account and it doesn't look like it is going to show up.
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Kash2nd Line EngineerCommented:
are there any bounce backs to the O365 users which you can post here?

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LockDown32OwnerAuthor Commented:
Not yet. That is the frustrating part. It took 3 days for Proofpoint to NDR. It has been 15 hours since I sent my test from my Outlook 365 account and no NDR yet.
LockDown32OwnerAuthor Commented:
Here is a bounce message that finally showed up.....
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LockDown32OwnerAuthor Commented:
Here is a bounce message:

From: Microsoft Outlook
Sent: Wednesday, August 05, 2015 10:49 AM
To: Richmond, Monty
Subject: Undeliverable: FW: New Hire for Benefits
Delivery has failed to these recipients or groups:
CarolJohnston (
Your message couldn't be delivered because the recipient's email system wasn't available when we tried to talk to it. It could be a temporary condition that may clear up soon.
Try to resend your message later. If it still doesn’t work, contact the recipient by some other means (by phone for example) and ask them to tell their email admin that their email system is having troubles accepting messages. The recipient’s email admin is the only one who can fix this.
For more information see Status code 4.4.7 in and Office 365.

Diagnostic information for administrators:
Generating server:
Receiving server: (
Total retry attempts: 175
8/5/2015 2:48:55 PM - Remote Server at ( returned '550 4.4.7 QUEUE.Expired; message expired'
8/5/2015 2:28:52 PM - Remote Server at ( returned '451 4.4.0 SMTPSEND.SuspiciousRemoteServerError; remote server disconnected abruptly; retry will be delayed'
Original message headers:
Received: from ( by ( with Microsoft SMTP
 Server (TLS) id; Mon, 3 Aug 2015 14:45:14 +0000
Received: from ([]) by ([]) with mapi id
 15.01.0225.018; Mon, 3 Aug 2015 14:45:14 +0000
From: "Richmond, Monty" <>
To: CarolJohnston <>
Subject: FW: New Hire for Benefits
Thread-Topic: New Hire for Benefits
Thread-Index: AdDKx3ysWJJJsLy1RlGk5yO6nqHwNwBkZaayAGh6WtA=
Date: Mon, 3 Aug 2015 14:45:13 +0000
Message-ID: <>
Accept-Language: en-US
Content-Language: en-US
authentication-results: spf=none (sender IP is );
x-originating-ip: []
x-microsoft-exchange-diagnostics: 1;BLUPR0601MB0994;5:QswxqVGdlxrfCTih2rfSPEIe6sI1s00DPA06hSWI5QQzdj5LAR023T2rJHGDFWhdyYiQ2GDC5k9TAPH/ax1MDqqTbLrbVOB77w4Urt1ViYbSnBAr/8R/WJj6wJQ/H9IYTF6qlT/9McPWDmN2tjqTHg==;24:KN3Kq5OXFf4l0dyBvnGhvI4vIVJ2qZVmxHMgyv+o8txnvTpkz3B/2DjeHMkUOkFblQj5mERWvtbxpKpc/rHBycL2e72TIsFZRpurKUS2l9I=;20:lmI+ShLLv2r3L92JbnCXZe5ENWxmfh3lFLkB36Uj1t5dhbr74/F0Orokljs0+Gsl8rHRtuLs1+wyxrI2i/FZAQ==
x-microsoft-antispam: UriScan:;BCL:0;PCL:0;RULEID:;SRVR:BLUPR0601MB0994;
x-microsoft-antispam-prvs: <>
x-exchange-antispam-report-test: UriScan:(108003899814671);
x-exchange-antispam-report-cfa-test: BCL:0;PCL:0;RULEID:(601004)(5005006)(3002001);SRVR:BLUPR0601MB0994;BCL:0;PCL:0;RULEID:;SRVR:BLUPR0601MB0994;
x-forefront-prvs: 0657D528EC
x-forefront-antispam-report: SFV:NSPM;SFS:(10009020)(6009001)(189002)(479174004)(377454003)(199003)(3905003)(19580405001)(5001860100001)(110136002)(19580395003)(54356999)(4001540100001)(2656002)(99286002)(86362001)(5001960100002)(50986999)(107886002)(5001830100001)(77156002)(101416001)(575784001)(106356001)(5890100001)(64706001)(62966003)(92566002)(5003600100002)(122556002)(66066001)(40100003)(450100001)(74316001)(189998001)(81156007)(46102003)(80792005)(68736005)(77096005)(105586002)(76576001)(33656002)(87936001)(5002640100001)(2900100001)(102836002)(15975445007)(97736004);DIR:OUT;SFP:1101;SCL:1;SRVR:BLUPR0601MB0994;;FPR:;SPF:None;PTR:InfoNoRecords;MX:1;A:1;LANG:en;
received-spf: None ( does not designate
 permitted sender hosts)
Content-Type: multipart/alternative;
MIME-Version: 1.0
X-MS-Exchange-CrossTenant-originalarrivaltime: 03 Aug 2015 14:45:13.9369
X-MS-Exchange-CrossTenant-fromentityheader: Hosted
X-MS-Exchange-CrossTenant-id: 3ec0e1ac-d5e6-49dd-a331-a09e30f18c75
X-MS-Exchange-Transport-CrossTenantHeadersStamped: BLUPR0601MB0994
Did you ever find a solution to this problem as we are having the exact same issue. Thanks.
LockDown32OwnerAuthor Commented:
Hi Graham,

   Not even close. No one has any idea and since it is Exchange 2003 no one is helping. It has to have something to do with the cert. If I re-key the cert it will receive for 4 or 5 hours and then I have to re-key the cert again. What a mess!
We installed a new cert as well but still having the same problem. I am now just looking into going to Office365 as I know we have been needing to upgrade our exchange server and this seems like the best and easiest cost reliable solution.
Where is the solution? I am having same issue. This is marked as the accepted solution yet I can't see it.
LockDown32OwnerAuthor Commented:
There was no answer to this. I just awarded points for trying. Since posting this I have come across several more people having the same issue. The general consensus is that Microsoft did something to force people off Exchange Server 2003. They changed encryption on Office 365 to be incompatible with the cipher of Exchange Server 2003 or something along that line.

   I moved to office 365 and ditched the Exchange Server...
We did the same thing. If you can't fight 'em, join 'em!
LockDown32OwnerAuthor Commented:
Yes and we all know how easy Microsoft is to fight :)
LockDown32, there is not a solution here.  This is a serious problem affecting many users still using exchange 2003.  Our company will not approve upgrading so I am stuck using exchange 2003, so I have no option but to find a solution or a work around.  You should un-accept this solution if you still can.
LockDown32OwnerAuthor Commented:
I agree Jamieson but what are you going to do? There is no solution. I am not a fan of Microsoft or what they do but Exchange Server 2003 is 12 years old and email is such a vital part of any company that upgrading should not be questioned. Your company isn't sure at this point what they are getting and what they aren't. They could be losing business left and right all because they won't update a 12 year old system. Welcome to 2015 :)
I agree 100%.  This is what I have been telling them for the past 2 years.
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