Emails with an apostrophe in the address fail to deliver

Question

I have a client who's email is hosted on Office365 and a user has reported that when they reply to a particular email it fails to deliver. The NDR reports the following error: SMTPSEND.Utf8RecipientAddress; UTF-8 recipient address not supported.

The email address that they are replying to contains an apostrophe and I wondered if this is significant. When my client replies to his customer he CCs in one of the customer's colleagues and this copy is delivered successfully.

As a test I created a user on my own Office365 tenant and gave the user an email address with an apostrophe. I emailed my client from this test user, which he received, and asked him to reply, which he did, but this also failed to deliver. The NDR reports the following: 550 5.1.10 RESOLVER.ADR.RecipientNotFound; Recipient not found by SMTP address lookup . When I sent an email to my test user from another mailbox, outside of Office365, the test delivered successfully.

The NDR my client receives when emailing his customer is as follows (I have changed server and user names for privacy):

esa7.mydomain.iphmx.com rejected your message to the following email addresses:
Gordon.O’Donovan@mydomain.com (Gordon.O’Donovan@mydomain.com)
The message couldn't be delivered because it contains characters that the recipient's email server doesn't recognize.
To fix this, set your email program to send messages using a different character set than UTF-8. In Outlook, for example, you can make this change in Options > Advanced > International options, then resend the message. If the problem continues, forward this message to your email admin.
For Email Admins
This issue occurred because the message was sent using the UTF-8 character set, which the receiving email system doesn't support. To fix this, the sender can try sending the message using a different, supported character set. Or if their mail server supports it, you can ask the recipient's email admin to configure their mail server to advertise support for SMTPUTF8, as specified in RFC 6531.
For more information, see Error code 5.1.17 in Exchange Online and Office 365.

esa7.mydomain.c3s2.iphmx.com gave this error:
SMTPSEND.Utf8RecipientAddress; UTF-8 recipient address not supported.

Diagnostic information for administrators:
Generating server: CWLP123MB4452.GBRP123.PROD.OUTLOOK.COM
Gordon.O’Donovan@mydomain.com
esa7.mydomain.c3s2.iphmx.com
Remote Server returned '550 5.1.17 SMTPSEND.Utf8RecipientAddress; UTF-8 recipient address not supported.'

Can anybody suggest why this error is occuring?

Thanks

David

Answer 1

Hi @Admin ,

The email address that they are replying to contains an apostrophe and I wondered if this is significant.

Is your client able to directly send a message to the particular email address witch contains an apostrophe?
How about manually typing the email address when replying the message?

If it works when manually typing the recipient's email address, this could be related to the autocomplete cache on the client's side. You can remove the problematic autocomplete entry by following the steps in this link.

If the issue persists, please go to Options > Advanced > International option, make sure the checkbox of "Automatically select encoding for outgoing messages" is selected:

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Answer 2

This option did not help me . I had to make user sign in to outlook web and send email from there .

thanks !

Answer 3

Can you guys at Microsoft confirm that the apostrophe is permitted in Outlook 365?

I was issued an email address with the apostrophe included. The IT department changed my email address without informing me. And now I cannot get into services that are registered with my old email (because password reset requests go to the old email address that I dont have access to)