Outlook (non-) Parsing of External Email Addresses

  • Thread starter Thread starter Fortune_Cookie
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Fortune_Cookie

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Firstly, apologies for the hideous redaction, hopefully my point is clear before we get there.

When pasting an email address into Outlook the email address is parsed and according to various MS docs, if external the email is encased in single quotes (this is expected behaviour and is fine).

Sometimes however, Outlook doesn't parse the address or some other mystery occurs and the email address is left without the quotes - this prevents Outlook from sending the email, indeed it doesn't even try to pass it to Exchange.

Enabling troubleshooting logging shows

2019.05.30 15:40:32 user@mydomain.com: Synch operation started (flags = 00000001)
2019.05.30 15:40:32 user@mydomain.com: UploadItems: 1 messages to send
2019.05.30 15:40:32 EXECUTING Put MAPI TASK
2019.05.30 15:40:33 Starting the Spooling Cycle
2019.05.30 15:40:33 MAPI Status: (IN -- ---/OUT fl ---)
2019.05.30 15:40:33 MAPI XP Call: FlushQueues, hr = 0x00000000, ulFlushFlags = 0x0000001a
2019.05.30 15:40:33 Sending one message
2019.05.30 15:40:33 Progress: Sending message 'SUBJECT' (size 649.73 KBytes)
2019.05.30 15:40:33 MAPI Status: (IN -- ---/OUT fl act)
2019.05.30 15:40:33 MAPI Status: (IN -- ---/OUT fl ---)
2019.05.30 15:40:33 MAPI XP Call: SubmitMessage, hr = 0x80040502
2019.05.30 15:40:33 MAPI XP Call: SubmitMessage returned MAPI_E_NOT_ME.
2019.05.30 15:40:33 FINISHED MAPI TASK

And Outlook generates an NDR with no headers and the content of:

Your message did not reach some or all of the intended recipients.

Subject: SUBJECT

Sent: 30/05/2019 14:12

The following recipient(s) cannot be reached:

<ExternalEmailAddress> on

The recipient has been deleted or has no email address.

For all of my testing I cannot work out how the users manage this, I have not been able to reproduce it on any of my machines (Outlook adds the quotes!), but the sent item maintains the non-quoted email address and resists sending.

There are reports of this issue dating back to 2010 (and possibly earlier) on the internet although nobody seems to have put all of these facts in one place, so here we are. Because this issue dates back so far I suspect my versions are unimportant, but for the record we are running Outlook 365 on Windows 10 with Exchange 2013 [which should also not be relevant].

1444959.png

Does anyone know if there's a way to make this work?

In the meantime I have recommended ctrl-k to the user when they paste.

Phill

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