Anybody having issues sending mail to Exchange online domains from European locations

I looked through the entirety of our ticket history and couldn't find another instance of this issue. That said, I agree that this doesn't appear to be at all related to SPF/DKIM/DMARC.

I was able to locate another person having this issue on Microsoft's Answers site, and Microsoft's solution was to have the user reach out to their O365 provider — do you have one of those? If so, I recommend asking them to strip these headers from your mail so that it isn't bounced by the recipient mail server. Alternatively they may be able to resolve this by simply not adding the header to begin with, however I'm not familiar enough with Exchange to know the implications of such a change.

If both your London and Frankfurt Linodes are communicating with the same O365 server adding that header, this would explain why you're only seeing the errors from that region.

Yes! We have the same problem for almost a week now. Messages from our Frankfurt servers are rejected from some Office365 tenants, but not all. It looks like a Microsoft issue and not a Linode one. We are going to open a ticket with them and try to figure this out. This is an example Office365 server response:

Nov 4 15:22:37 node-06 postfix/smtp[186181]: AC3EEDDF8A: to=xxxxxxxxxx@xxxxxxxxxx.xxx, relay=xxxxxxxxxx-xxx.mail.protection.outlook.com[104.47.17.74]:25, delay=0.86, delays=0.01/0.02/0.26/0.58, dsn=5.6.211, status=bounced (host xxxxxxxxxx-xxx.mail.protection.outlook.com[104.47.17.74] said: 554 5.6.211 Invalid MIME Content: Single text value size (32799) exceeded allowed maximum (32768) for the 'X-Matching-Connectors' header. [AM6PR06MB4470.eurprd06.prod.outlook.com] [DBBPR09CA0002.eurprd09.prod.outlook.com] [DB8EUR05FT005.eop-eur05.prod.protection.outlook.com] (in reply to end of DATA command))

Hi there,

we are seeing the same issue since one month: Sending mails from our postfix mailserver located in Frankfurt results in this strange error complaining about the never set 'X-Matching-Connectors' header exceeding 32k.

This happens with very plain emails, with only the bare minimum of headers set – even trying to communicate with the Office365 servers with telnet from one of our Frankfurt servers returns the error.

We don't have any connection to Office 365 (or a provider to reach out to). We simply trying to deliver mails to addresses served by Office 365 mailservers.

We already tried to contact MS on serveral channels and created various tickets. I'll keep this thread updated, but it would be very helpful if Linode could reach out to MS. Especially since this now seems to be a problem for several Linode customers.

Same problem with outgoing emails to Office365 from our Linode mail server located in London

xxxxx@xxx.com: host
xxxxx-com.mail.protection.outlook.com[104.47.18.74] said: 554 5.6.211
Invalid MIME Content: Single text value size (32799) exceeded allowed
maximum (32768) for the 'X-Matching-Connectors' header.
[VI1P190MB0478.EURP190.PROD.OUTLOOK.COM]
[AM5PR04CA0022.eurprd04.prod.outlook.com]
[AM6EUR05FT016.eop-eur05.prod.protection.outlook.com] (in reply to end of DATA command)

I have the same problem with a normal email that was set to microsoft services (outlook.com / live.com / hotmail… and clients with 365 services).

We sent emails without problems for years but in the last 5days the email bounces.

The problem is

host cosfer-it0i.mail.protection.outlook.com[104.47.18.74]
said: 554 5.6.211 Invalid MIME Content: Single text value size (32799)
exceeded allowed maximum (32768) for the 'X-Matching-Connectors' header.
[DB9PR01MB7484.eurprd01.prod.exchangelabs.com]
[AM6PR04CA0028.eurprd04.prod.outlook.com]
[AM6EUR05FT007.eop-eur05.prod.protection.outlook.com] (in reply to end of
DATA command)

We use zimbra and the server doesn't add "X-Matching-Connectors" that is evaluate and autocreate by microsoft side.

We have used a different smtp relay server and all works fine, the problem is relative to linode server.

This started happening from London servers, too.

For years everything was fine and dandy…

I opened a support ticket, but no answers so far.

We are having the same problem.

Postfix server on Linode Frankfurt.

I have also asked for help here:
https://www.linode.com/community/questions/22063/anybody-having-issues-sending-mail-to-exchange-online-domains-from-european-loca

And one of our customers (an O365 customer) has opened a ticket at their provider.

O365 server response after DATA command:

554 5.6.211 Invalid MIME Content: Single text value size (32799) exceeded allowed maximum (32768) for the 'X-Matching-Connectors' header.

(But no such header is in the mail)

Not all o365 tenants are affected.

Still trying to work with Microsoft on this one, but having trouble getting through to them that we're not the ones adding the header - it's their own servers adding the header.

I've verified this by sending mail directly with SMTP using no more than "MAIL From" and "RCPT TO" in the envelope header and "To", "From" and "Subject" in the message header.

Would be interesting to know if it only affects traffic routed through 172.104.0.0/15 (LINODE-US AS3595, AS63949, AS21844, AS8001, AS6939) and 212.111.40.0/22 (Linode AS15830). Perhaps Microsoft is doing some additional anti-spam filtering on mails sourced from here and it's getting into a loop?

Hey there folks,

I wanted to follow up here for those who are seeing this issue. After reaching out to our networking administrators we are able to confirm this is not an infrastructure issue. They also were able to clarify that is unrelated to our hardware.

To rule out the possibility that these (or any) headers get added before mail leaves our network, our network admin also clarified that we do not perform any packet or data modification.

Hi,

We're having same issue with sending to O365 from linode, haven't seen this from our mail servers in another locations at least yet. Mails to some recipients in O365 go through normally but some bounce back with that 554 5.6.211 error.

Anybody heard from Microsoft side yet?

We have an open service request with Microsoft (case #‎28163446‎ if anyone want to reference it with their own MS cases).

I think I've persuaded them that we're really not generating the X-Matching-Connectors header on our side and they say their investigating why some European mail gateways are making the header grow.

The recipient of our messages who is using MSO365 already opened a ticket with no luck.
Microsoft and Linode are rebouncing the problem each other.

In the meantime I found a possible explanation that is located in the middle and caused by a known bug with Cisco IronPort Email Security Appliance Software.

Large Ironport-PHdr header causing 5.6.0 errors - Cisco Community

Cisco Bug: CSCuw09558 - Large Ironport-PHdr header does not fold causing delivery problems

If not solved in a couple of weeks I'll have to migrate all my email to a reliable service provider.

Never had any problem sending from Frankfurt to Exchange.

Done that for over 5+years now on same IP.

Hi @Marco

I believe the Ironport issues would only happen if the destination tenant had a connector going to an Ironport system to scan email.

From the tests I've done, the problem is occurring without any external tools.

We've been trying to dig through this problem, and the rough flow of the issue is:

1. MTA attempts to deliver to someone@365-domain.com
2. MTA resolves MX for 365-domain.com to 365-domain-com.mail.protection.outlook.com
3. MTA resolves A records for 365-domain-com.mail.protection.outlook.com as a couple of servers in mail-*.inbound.protection.outlook.com. These are inbound mail servers in the same geographic location as the tenancy
4. MTA connects to one of the inbound mail servers and attempts mail delivery
5. The inbound mail server accepts the MAIL FROM, RCPT TO and mail message content
6. The inbound mail server determines how to route the mail to whatever internal exchange server is handling the mail. This adds the X-Matching-Connectors header to the message headers
7. In some cases, the X-Matching-Connectors header is now larger than 32k which causes processing of the mail to stop and an "554 5.6.211 Invalid MIME Content" status response sent back to the MTA

It seems to be in step 6 that the problem occurs. It looks like the source address of the SMTP connection is used to determine what the matching connectors are.

Our customers have attempted to get message traces for the test messages we're sending them, but they don't see any. To me, this indicates the offending header is getting added early in the mail processing, before it's even had a chance to get to the servers hosting the tenant's exchange instance.

It's possible the X-Matching-Connectors header is simply a list of all the possible connectors the mail can be handled by on its way from the inbound gateways to the tenant exchange. If that's the case, then as MSFT have grown their infrastructure, the list of matching connectors has grown leading to a header size >32k. At this point, mail processing stops because the header is too big. Unfortunately, I can't find any public documentation about the header, so this is just a guess based on the header name!

Further details that may help to understand
Ex2010. A parsing error has occurred: MIME content error: Single text value size (33027) exceeded allowed maximum (32768)

Hello,

have same issue with Microsoft 365 recipients. Here one example which was delivered:
X-EOPAttributedMessage: 0
X-EOPTenantAttributedMessage: e07c9d1c-06dc-4644-a8d2-196910eff6c7:0
X-Matching-Connectors:
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=?us-ascii?Q?-4c58-4770-8b70-08d9924b6891,71ccfe52-f184-4642-b700-08d99b2?=
=?us-ascii?Q?68bfd,d818f410-cb64-4941-13e3-08d9887c1d4d,f48bb021-f0f7-4de?=
=?us-ascii?Q?a-ba6c-08d99b289592,0b9b8fc7-b186-4574-02d3-08d985480504,164?=
=?us-ascii?Q?2eadd-bbb0-472f-79c1-08d99759efcc,ae86fd10-5f42-4c96-2873-08?=
=?us-ascii?Q?d99570556e,a08fd120-c4ce-47f3-93ca-08d9864f04ff,89b9b7a3-7ee?=
=?us-ascii?Q?3-4ded-b9d4-08d992bf1e87,f9d6ce89-e7e6-4879-7d03-08d997c9d57?=
=?us-ascii?Q?c,664b7280-f420-469e-49af-08d99b40edc7,a614e072-a51f-47a5-e1?=
=?us-ascii?Q?83-08d9866c4e28,038f418c-aaa7-4134-fbf2-08d99b2c63ed,dbc914d?=
=?us-ascii?Q?c-f9eb-4f53-0e33-08d99b944542,4645e6be-21ff-44da-0eeb-08d99b?=
=?us-ascii?Q?1e90bf,a3e4830d-c92d-4e55-fb31-08d98665a65d,af965875-65d0-4e?=
=?us-ascii?Q?10-5f8f-08d99a6fb41c,226f08ac-03f2-4235-d92e-08d9885daa97,b8?=
=?us-ascii?Q?35cd12-fdb6-450e-616a-08d9924cde44,ba2e2417-1b32-4cc3-4ceb-0?=
=?us-ascii?Q?8d997baff8b,77e8071f-eef1-4df2-0ece-08d98671a967,01f19104-ff?=
=?us-ascii?Q?45-4dfa-0cf5-08d99754e105,1b9b1b94-0d42-429a-379b-08d99b6d2b?=
=?us-ascii?Q?4d,d8c451cd-dcf4-4b4e-9d1b-08d98686e536,3abf9c5d-0b68-4acd-4?=
=?us-ascii?Q?7aa-08d99b1710aa,37a1feee-fe4c-435f-7813-08d99958a3f5,061c74?=
=?us-ascii?Q?80-9946-43be-25f6-08d98767d407,c811c762-571c-45a6-86a2-08d99?=
=?us-ascii?Q?b1912fc,70bc1921-b1f5-4f63-7dce-08d99942b60e,b4d19751-0341-4?=
=?us-ascii?Q?be7-34d1-08d99b94dd67,f13aab59-761d-4474-0407-08d99ceaadf5,c?=
=?us-ascii?Q?7cff232-148c-488b-7c5e-08d9877a19e2,1a7cd4f0-2861-4a75-9ef2-?=
=?us-ascii?Q?08d99240066e,b66f554b-c3bf-40d7-4916-08d9868d99a1,4d557ea9-b?=
=?us-ascii?Q?01a-4f1f-983f-08d99242c8de,0aea2ab6-6f08-4c0e-b176-08d99b386?=
=?us-ascii?Q?d3d,804004fd-125d-4e2b-123a-08d99514e5a8,e0c132fe-1b04-4456-?=
=?us-ascii?Q?359c-08d99af4d2d4,bc10cde2-bb40-403e-2e9e-08d999459878,ea4ef?=
=?us-ascii?Q?279-80a3-4aa5-9f75-08d99b8f5298,ba40532d-1fa7-4c54-a6f5-08d9?=
=?us-ascii?Q?88826451,741c6c1c-421b-4759-6311-08d9952049cb,b155ea8f-a679-?=
=?us-ascii?Q?48ff-c8d7-08d997c272d2,65ec10d9-18da-4908-c36d-08d99256fbcd,?=
=?us-ascii?Q?3441949a-ece2-43b5-7a1f-08d99b774e29,f5ff4e57-0e73-4a28-1dbd?=
=?us-ascii?Q?-08d992441b4a,99bec7ee-40ef-4f13-b122-08d99b199f13,0fcfac84-?=
=?us-ascii?Q?a9f0-4eed-2dd9-08d986647e19,5e46b120-c010-415d-a50b-08d99b47?=
=?us-ascii?Q?372a,6aff5c10-1a20-4b7b-e8bd-08d9864a4aab,2b4e367d-08c8-4ea5?=
=?us-ascii?Q?-9140-08d988771071,c1bb2461-a25d-4bc5-17c6-08d998e6178b,a656?=
=?us-ascii?Q?a9a5-4cac-412f-6607-08d997bc8ea7,3e890cd2-18dd-4035-5cb9-08d?=
=?us-ascii?Q?992bdaa0d,379148ca-01e2-4ad7-89c7-08d986998f09,f90f11ae-222b?=
=?us-ascii?Q?-4dd3-3617-08d986581434,4fdf1b9d-ce1f-4c8e-b850-08d9867f8483?=
=?us-ascii?Q?,16fa0e45-5067-4202-2c7d-08d98866d492,b3e5d57b-edf2-4753-5ba?=
=?us-ascii?Q?d-08d98881280b,b7ad0f94-fedc-4f4d-1bb8-08d995223a43,8946dd06?=
=?us-ascii?Q?-6b78-434c-5a05-08d99b59d53f,fa230d4c-d7d1-449b-ae36-08d9865?=
=?us-ascii?Q?a849c,4de4e7f1-c4ab-4460-bc10-08d99b123935,b06862eb-1d3b-448?=
=?us-ascii?Q?f-a95d-08d9885bb4db,50468c47-8a37-43f1-b0d9-08d9925654b1,fe6?=
=?us-ascii?Q?a8ae0-6e71-4648-39cf-08d9885af30a,68b7bb63-2e36-4c41-152f-08?=
=?us-ascii?Q?d9975852b3,4317b96d-fa2c-4283-2a8b-08d986516adc,dad3ca23-555?=
=?us-ascii?Q?d-460b-f1d8-08d98762f7e6,fd28273b-fe88-4398-3a51-08d9864dd43?=
=?us-ascii?Q?8,cda1297f-f19a-445f-df49-08d985811b9b,fcb1c674-1cfd-49bf-8d?=
=?us-ascii?Q?f4-08d99b9282b5,8e18a8ef-9bc0-468c-82a7-08d9886e40d3,3b3c2bd?=
=?us-ascii?Q?0-b69c-4b03-4fc2-08d99b9d0286,05e77ea0-0adc-4dce-2a83-08d986?=
=?us-ascii?Q?9321d4,4a168a8d-4900-4f68-56af-08d98892f791,2ffdd0d0-a958-48?=
=?us-ascii?Q?db-cca6-08d997b7a4a4,4135e363-7257-4553-0b3e-08d9889f4e6f,87?=
=?us-ascii?Q?72c01a-af51-409d-ea81-08d9974ccebc,f9639d04-821f-4e44-e5cf-0?=
=?us-ascii?Q?8d987169d8a,1bf0301a-a38d-469d-3ea5-08d99b63d845,20190fdb-62?=
=?us-ascii?Q?a3-493f-4231-08d99b8120fd,8f707a26-3758-4c9c-ceb3-08d99b7f1a?=
=?us-ascii?Q?86,71faa599-f0cc-46ae-4528-08d98662b959,a4933d73-1936-4ca6-0?=
=?us-ascii?Q?1ea-08d9888709c9,6f699c6f-39e7-4a54-5c1a-08d9866f42cb,e33c9c?=
=?us-ascii?Q?32-e14f-4831-8aba-08d99b76c2aa,d7f8dfa1-267f-4c87-604f-08d99?=
=?us-ascii?Q?5168428,db2adcd5-184b-4e50-3abb-08d98653ccac,9741c7de-cd57-4?=
=?us-ascii?Q?0de-0431-08d9867071f0,b51e8a14-0ad2-4954-edcd-08d99b322a34,9?=
=?us-ascii?Q?3c6b060-58e2-4786-6017-08d987216a69,4094d543-77cb-45d5-b026-?=
=?us-ascii?Q?08d9888e7cad,3f36b039-e9f0-4966-f73f-08d9869517fc,0a6feb21-b?=
=?us-ascii?Q?2da-4452-1abb-08d9869d44d3,7aedff1b-7bf7-4940-847b-08d98631d?=
=?us-ascii?Q?13c,5e2e14e0-1f4d-4ed2-04aa-08d986456f07,a818de03-5d5a-41ad-?=
=?us-ascii?Q?9d38-08d988910981,e2796792-a9c8-4c7f-a71f-08d98891a8fb,5f184?=
=?us-ascii?Q?57d-e4fa-49dc-592e-08d99517c6c4,2abcaf6f-a425-48b6-9dc1-08d9?=
=?us-ascii?Q?868455ff,7477d995-30a1-447a-2024-08d9877b9a17,7aedc8dc-e19d-?=
=?us-ascii?Q?401f-f4cf-08d9866d7824,16064ac9-dbad-4590-18ba-08d9863a1058,?=
=?us-ascii?Q?683c6c02-142e-4c4c-d1b5-08d9889b49fd,4b613e35-04a3-4551-a595?=
=?us-ascii?Q?-08d9866ce323,5b005f33-9a67-4415-66ae-08d9853c455c,7f3d13a2-?=
=?us-ascii?Q?581b-47bf-3609-08d99b659a72,20c30e5b-5bb8-486c-3040-08d9974b?=
=?us-ascii?Q?b714,6b7c8b7c-ff25-4b8b-aef8-08d98644da53,4e1364f4-d5f8-4897?=
=?us-ascii?Q?-d0a8-08d9886baaec,44adbabd-e834-4f51-8e34-08d99b9088d2,f895?=
=?us-ascii?Q?ad36-23d9-44f2-9730-08d986801ff4,b03112e7-ae90-4a4a-3b58-08d?=
=?us-ascii?Q?9855077b1,03a77f6f-194b-45b6-dbc5-08d985717304,6dbf392e-bad3?=
=?us-ascii?Q?-4a50-3252-08d99b2282b4,b0aad7de-e12f-4a77-0bdb-08d99b8392b9?=
=?us-ascii?Q?,70e7da90-2633-4ea8-a9bc-08d9959e2dbe,b9d59c78-bd5d-4b0c-9b0?=
=?us-ascii?Q?6-08d99b7958fa,89850c86-88be-4e3b-1bbe-08d99947768a,14b24857?=
=?us-ascii?Q?-9d07-490f-ea87-08d986901c5c,defbf388-403a-40bc-9427-08d997b?=
=?us-ascii?Q?a7637,cbb2343d-be3c-4c57-b739-08d99b4c776e,3a1a3674-3f32-495?=
=?us-ascii?Q?b-74a4-08d98663e8ea,45aa0b00-70f5-45d9-7172-08d9854036dd,68d?=
=?us-ascii?Q?cf1dc-7e4a-49b7-b681-08d98688b37b,5b506c22-6da3-4e1a-a6a0-08?=
=?us-ascii?Q?d995b7f909,5201f456-4c88-41e7-cfbc-08d9862c7333,6940be68-4fa?=
=?us-ascii?Q?c-4e8f-6f3d-08d99b39b005,6e44d8c1-7a01-4d6b-b68d-08d98689f78?=
=?us-ascii?Q?3,d2f2fb59-0574-4369-296c-08d99b6fa211,7b1baad0-ef56-4f01-eb?=
=?us-ascii?Q?5e-08d99b9ba9fa,5475eeb5-5a22-4c2c-c51f-08d997b71445,67f0882?=
=?us-ascii?Q?e-6e97-42b6-7fb4-08d9864877b6,8bfa1f38-8d30-47cc-9e94-08d99b?=
=?us-ascii?Q?882bec,670b1382-4ef5-4be9-bd17-08d998e27f66,c829b76d-6e98-46?=
=?us-ascii?Q?6f-052a-08d99cf53c7c,e1659a8b-c49a-433a-9580-08d98677ad13,19?=
=?us-ascii?Q?3a88d4-c98d-4d09-ee4d-08d9862a1c92,a8a061c6-34a8-45f7-0913-0?=
=?us-ascii?Q?8d9876726f0,d975cc42-7a41-4435-3df1-08d99b99d023,4f3a1200-9a?=
=?us-ascii?Q?2c-4d3e-5f3a-08d99b8d797c,3da6c1e6-5249-4764-8107-08d99b7428?=
=?us-ascii?Q?ac,06b44eeb-2ff0-45a1-7710-08d98879a9ed,91c497df-e17e-44f7-3?=
=?us-ascii?Q?7ed-08d99b220825,b35d613e-8c63-402e-2532-08d988807dbd,e95c7f?=
=?us-ascii?Q?c9-7f58-4d06-3cae-08d98635ed5d,c35c1644-10c9-46fb-d057-08d98?=
=?us-ascii?Q?6401143,e8af2621-4412-4b2d-b116-08d986634d08,7a39e6d3-a185-4?=
=?us-ascii?Q?d85-f3ca-08d9887b7efb,7b2edd46-cdb7-40ce-5a7c-08d99b679ae5,d?=
=?us-ascii?Q?78714fe-b900-49bb-79ea-08d99b75f834,582dac05-375e-4794-139a-?=
=?us-ascii?Q?08d998eb94e3,7b74bc4e-673a-4b14-bda9-08d9865e0cee,be4118d8-7?=
=?us-ascii?Q?d97-4dd8-04ee-08d99b2588f9,21146a85-46fc-4439-cbe3-08d9975a7?=
=?us-ascii?Q?282,2e3d8dfb-e5ae-4d4e-6579-08d985511264,f385f456-0d69-428f-?=
=?us-ascii?Q?852e-08d9888acd3d,9faee5b9-0aa7-4ed3-808f-08d9975b01a6,10edd?=
=?us-ascii?Q?707-f622-4573-ae4d-08d99b72d9f2,e910d603-2c7e-4481-6094-08d9?=
=?us-ascii?Q?866bbaaa,bd2307dc-2e45-4f19-594e-08d9853bae75,88220a47-1167-?=
=?us-ascii?Q?4c28-e957-08d9888cade0,6301d7d0-1b19-46d5-7dab-08d9853e157d,?=
=?us-ascii?Q?16ff6dc9-8443-4e91-dd69-08d98877b362,492b9169-b599-445e-bfab?=
=?us-ascii?Q?-08d9863b3675,8611f21b-6e24-4383-ba13-08d997b6897a,3f0d28bd-?=
=?us-ascii?Q?05ef-4e78-e7ee-08d997c157f9,f51128b3-f18e-48fb-759d-08d99b54?=
=?us-ascii?Q?70a3,49bad9e6-dcc1-4a31-0748-08d99571cd8b,7447d57f-f941-4801?=
=?us-ascii?Q?-cea8-08d99b56ba60,567e16eb-08ca-492d-7ef8-08d99b97c930,e8c4?=
=?us-ascii?Q?6497-bb51-4569-4b67-08d9866fdebe,d051555a-2c57-487a-2924-08d?=
=?us-ascii?Q?9994622d9,03e8f606-6b1c-4fac-9b06-08d98634c116,e5bb18b7-fbec?=
=?us-ascii?Q?-46db-126d-08d997c76756,0a6e73cd-9c2c-47c5-e6a9-08d99b9d9d04?=
=?us-ascii?Q?,1983b8e0-74dc-4167-2fce-08d99b3ad7fb,6048f5ee-9ffb-40ab-231?=
=?us-ascii?Q?8-08d986326550,3996aeb0-60a9-4949-60e8-08d99b3bea6b,cbe48e39?=
=?us-ascii?Q?-eb81-48da-f07f-08d99b270add,423756c3-e3a2-4e5a-1827-08d9865?=
=?us-ascii?Q?f3b4b,cfeb75f1-f5ce-4363-65fd-08d9951c923a,33ac81f2-96a2-4d2?=
=?us-ascii?Q?0-b956-08d99b58add4,8b2ed278-158d-47ae-f3b9-08d987203c38,16e?=
=?us-ascii?Q?837d8-f197-4547-2054-08d98c0f6dfa,24bf219e-0e9b-4d27-2695-08?=
=?us-ascii?Q?d986491832,3bbfe094-bea8-4a22-069a-08d9869687ea,c6cf4f50-b2c?=
=?us-ascii?Q?7-4a4f-6f36-08d985555e31,90e10dfe-5d7d-492f-7a34-08d99248b21?=
=?us-ascii?Q?a,3d47d283-7500-4c01-6583-08d99b68b99b,50b53cad-9e87-4f44-0d?=
=?us-ascii?Q?81-08d9957272ec,9800a72b-1d6d-47e6-64b8-08d98646af6c,f240043?=
=?us-ascii?Q?a-2708-43a7-19ac-08d99b577ed1,15c65d1d-dd9e-41a0-249a-08d986?=
=?us-ascii?Q?6ea29d,3e598d1a-7712-435f-ada8-08d99752e685,66cd4e02-ef8b-45?=
=?us-ascii?Q?74-b0e8-08d99b9c4653,804cb557-9b75-4dd8-5477-08d99cf38649,a0?=
=?us-ascii?Q?299c9c-76be-4cb8-c2e7-08d986b23595,32b26c86-5370-4503-5da5-0?=
=?us-ascii?Q?8d98c1ec41c,7187497e-660a-43e6-0bd0-08d985524941,2f01d509-79?=
=?us-ascii?Q?49-41b7-a4d1-08d9863ee3dc,15610e4f-d398-426e-289b-08d9887162?=
=?us-ascii?Q?61,caedf4df-3b66-4928-0884-08d9866b1a09,7fb902aa-b59d-4bf8-9?=
=?us-ascii?Q?17f-08d99b9b09a1,6276f30c-357a-4695-7317-08d998ec1b85,e72a42?=
=?us-ascii?Q?4d-5f84-46de-683c-08d9974de836,18b29503-32c2-4f8c-12f7-08d98?=
=?us-ascii?Q?8a2510d,dc7a63ff-a2c8-444e-17c2-08d99240aa44,538a94bd-434f-4?=
=?us-ascii?Q?47b-042b-08d99522e006,45448e0a-6670-4f85-bccf-08d988

Here are bouncing European MS 365 hosts

[AM7PR02MB6211.eurprd02.prod.outlook.com] [AM3PR03CA0058.eurprd03.prod.outlook.com] [VI1EUR05FT009.eop-eur05.prod.protection.outlook.com]
[DU2PR02MB7807.eurprd02.prod.outlook.com] [AM6PR05CA0008.eurprd05.prod.outlook.com] [AM6EUR05FT068.eop-eur05.prod.protection.outlook.com]
[PAXPR02MB7311.eurprd02.prod.outlook.com] [DB6PR0801CA0051.eurprd08.prod.outlook.com] [DB8EUR05FT025.eop-eur05.prod.protection.outlook.com]
VI1PR02MB3071.eurprd02.prod.outlook.com] [AM6PR0202CA0060.eurprd02.prod.outlook.com] [AM6EUR05FT061.eop-eur05.prod.protection.outlook.com]
[AM9PR02MB7692.eurprd02.prod.outlook.com] [DB6PR0501CA0017.eurprd05.prod.outlook.com] [DB8EUR05FT037.eop-eur05.prod.protection.outlook.com]
[DU2PR02MB7576.eurprd02.prod.outlook.com] [DB8PR03CA0001.eurprd03.prod.outlook.com] [DB8EUR05FT024.eop-eur05.prod.protection.outlook.com]
[VI1PR02MB4031.eurprd02.prod.outlook.com] [DB6PR0202CA0022.eurprd02.prod.outlook.com] [DB8EUR05FT047.eop-eur05.prod.protection.outlook.com]
[AM4PR02MB3185.eurprd02.prod.outlook.com] [AS8P250CA0015.EURP250.PROD.OUTLOOK.COM] [AM6EUR05FT061.eop-eur05.prod.protection.outlook.com]
[AM6PR02MB4950.eurprd02.prod.outlook.com] [DB6PR0802CA0042.eurprd08.prod.outlook.com] [DB8EUR05FT023.eop-eur05.prod.protection.outlook.com]
[DB9PR02MB7148.eurprd02.prod.outlook.com] [AM5PR1001CA0072.EURPRD10.PROD.OUTLOOK.COM] [VI1EUR05FT019.eop-eur05.prod.protection.outlook.com]
[AM8PR09MB5367.eurprd09.prod.outlook.com] [DB6PR07CA0179.eurprd07.prod.outlook.com] [DB8EUR05FT024.eop-eur05.prod.protection.outlook.com]

But for instande these are ok:

AM6PR10CA0059.EURPRD10.PROD.OUTLOOK.COM
AM6PR08CA0012.eurprd08.prod.outlook.com
AM7PR03MB6610.eurprd03.prod.outlook.com
DB9PR03MB7419.eurprd03.prod.outlook.com
AM5EUR03FT039.eop-EUR03.prod.protection.outlook.com

Even if sender domain and IP is whitelisted at MS Exchange mesages are not delivered. I opened ticket with MS but to no avail. The bouncing messages are not logged anywhere at Microsoft, so bounces do not exist for them. Message trace in EOP is also not showing any of the rejected messages. We have to come to an ende. Clients are suffering a lot becaus of this new Microsoft 365 Defender "Feature".

BR Lautrivta

My latest update from Microsoft is that internal teams are "checking your concern", which is giving me a bit of a Raiders of the Lost Ark "top-men" vibe :(

My update today from Microsoft 365 Support: "This is to inform you that we are still discussing the this case with our senior resources and we will contact you accordingly once there is an update."

Any Message from Webmail to "broken" MS 365 host is not bouncing, but shows a huge "X-Matching-Connectors" header. Same Message from client device is bouncong with sad "554 5.6.211 Invalid MIME Content: Single text value size (32799) exceeded allowed maximum (32768) for the 'X-Matching-Connectors' header." message. Public MS Exchange documentation does not show any 554 5.6.211 Error information.

Hi all - I just wanted to reassure everyone that we have already investigated this on our end and our administrators have confirmed that this issues is is not an infrastructure issue. We hope that Microsoft is able to internally resolve this issue for the people who are affected.

The problem still persists… You should start some STOP USING MS365 campaign or something if they don't listen :(

My latest from Microsoft is that this has been escalated to the product team.

Yesterdays reply from MS: "the issue is from sender's end and not from Microsoft's end”

"As per our discussion over the phone, We have analyzed the SMTP logs collected from senders and we have discussed this with SEE. As per the logs the issue is from sender's end and not from Microsoft's end. If you need any assistance I would request you to please reply to this email with a good callback time.

It would be our pleasure to assist you with your office 365 subscription."

Time to take legal actions ?

Microsofts 365 'X-Matching-Connectors' header issue is related to messages sent with Microsoft Outlook from a mailbox to certain Microsoft 365 hosts in Europe. If message is sent with Webmail, Thunderbird or Mailspring, X-Matching-Connectors' header is hugh (31 kB), DKIM body hash does not verify but message is delivered.

@Lautrivta A client of mine uses Thunderbird, and every mailing to MO365 users in Europe causes a bounce back, and emails are not delivered.

@Frugan I am in Europe, maybe thats why X-Matching-Connectors header is "only" 31 kB. I send message from Frankfurt, MS 365 is receiving message in Vienna, forward it to Amsterdam and from there back to Vienna and again to Amsterdam.

Hop Delay From By With Time (UTC)
1 * 80.123.111.228 serv03.atvirtual.eu esmtpsa (TLS1.2) tls TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256 (Exim 4.94.2) (envelope-from contact@atvirtual.nl) 12/11/2021 8:46:24 AM

2 0 seconds serv03.atvirtual.eu 192.46.236.134 VI1EUR05FT039.mail.protection.outlook.com 10.233.243.0 Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) 12/11/2021 8:46:24 AM

3 1 Second VI1EUR05FT039.eop-eur05.prod.protection.outlook.com 2603:10a6:203:8f:cafe::1a AM5P194CA0023.outlook.office365.com 2603:10a6:203:8f::33 Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) 12/11/2021 8:46:25 AM

4 0 seconds AM5P194CA0023.EURP194.PROD.OUTLOOK.COM 2603:10a6:203:8f::33 VI1PR02MB3150.eurprd02.prod.outlook.com 2603:10a6:802:18::27 Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) 12/11/2021 8:46:25 AM

5 2 seconds VI1PR02MB3150.eurprd02.prod.outlook.com 2603:10a6:802:18::27 AM0PR02MB4993.eurprd02.prod.outlook.com HTTPS 12/11/2021 8:46:27 AM

Microsoft Support after 30 days of open ticket:
"As per the logs the issue is from sender's end and not from Microsoft's end". Our Clients: "If we can't send messages with your servers to our business partners with MS 365 accounts we have to move to MS 365 ourself". A Microsoft business model? Anyway a nightmare.

@Lautrivta Thanks for the reply..
My client also sends emails from a Linode based in Frankfurt, to MS 365 users based in Europe.
He uses Thunderbird, and every mail is bounced back.
Just hearing "Microsoft" gives me hives..

I'm having the same issue. Had it on London host and now also on Frankfurt.
"host XXX.mail.protection.outlook.com[X.X.X.X] said: 554 5.6.211 Invalid MIME Content: Single text value size (32799) exceeded allowed maximum (32768) for the 'X-Matching-Connectors' h
eader. [AM9PR06MB7219.eurprd06.prod.outlook.com] [AM5PR0602CA0023.eurprd06.prod.outlook.com] [AM6EUR05FT016.eop-eur05.prod.protection.outlook.com] (in reply to end of DATA command))
"

I will move our email server away from linode since it's obvious they can't resolve this issue.

@asistdoo a curiosity: does this happen to you with any email client (Outlook, Thunderbird, etc.)? Or just with some?

@Frugan I don't think its related to clients. Do you think it's related to clients and why?

I've migrated to Frankfurt from London. Problem reappeared. @#$%$

@asistdoo My client claims that sending with Machinstosh's Mail program works, while Thunderbird does not.
However, I have not been able to verify for myself if it is true ..

X-Matching-Connectors header issue at some European MS 365 hosts resolved since yesterday evening.

Oops. There are more MS 365 hosts left unresolved.

554 5.6.211 Invalid MIME Content: Single text value size (32784) exceeded allowed maximum (32768) for the 'X-Matching-Connectors' header.

104.47.11.138 Frankfurt
104.47.7.138 Berlin

OK (no 'X-Matching-Connectors' in header)

104.47.17.138 Wien
104.47.18.74 Amsterdam