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UtterAccess Forums _ Microsoft Outlook _ Undeliverable mail when replying

Posted by: mashed_monster Mar 9 2006, 09:18 AM

He have a user who can send email to a specific addres (i.e. a brand new email), however when he replies to a message from the same person, it doesn't get there and he gets an undeliverable message.
I have no idea how this can happen, any ideas?

Posted by: LakeGator Mar 9 2006, 10:27 AM

I assume you have verified that the address in the reply-to is the exact correct address? It is possible to have a reply-to address that is different than the actual sender and it is POSSIBLE that there was some sort of typographical error in it.
On experiment might be to have your victim do a reply to this person and enter the personís address in the CC of the message.
What is the error in the undeliverable message? The assumption is that it is addressee not found but it could be other things like some sort of spam block.

Posted by: mashed_monster Mar 9 2006, 11:06 AM

Yes, verified the address. I successfully emailed the address when I copied it from the undeliverable message, unfortunately the undeliverable only says the recipient cannot be reached. I've replied from the guy having the problem and 'ccd' my hotmail account to see if it gets to either of them. That should at least narrow down to whether or not it's only this one address or all addresses.
I'll post again when I have the result of that one,
Thanks for your time:)

Posted by: LakeGator Mar 9 2006, 11:15 AM

You might be able to get more information by using the Options while reading the message. It depends on the version of Outlook but this is generally available via View -> Options. You will want to look through the Internet headers at the bottom.
That you are looking for is the actual reply-to address and, most importantly, any SMTP errors in the message. A typical SMTP error looks something like 5.5.0 smtp;550 Requested action not taken: mailbox unavailable. The 5.5.0 is the status code and this can often help determine what is causing the failure.

Posted by: DanielPineault Dec 6 2019, 05:35 AM

It's funny you post this question as I am investigating a similar issue where a user cannot forward email from one particular source.

One thing to try is to disable your anti-virus, anti-malware for 5-10 minutes and see it your emails go through.
On the odd chance, check rules and junk blocked senders ...
Run a scanpst.exe on the Outlook PSTs until no errors are reported.