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I was called to a user who has a peculiar issue in outlook. The problem is the following.

He got a mail from someone and when he tries to reply to it, the reply mail sets him (the reciever) as the target in the "To"-field. However in an earlier mail, when he does the same, it sets the sender (the person who send the mail) correctly. It doesn't make a difference if he clicks on reply or reply all.

Here an example to visualize this issue. You recieve a mail from [email protected] to your address [email protected]. When you click on reply (all) outlook tries to send the mail to [email protected] instead of [email protected].

We are using office 365 and his outlook is version 2019 / the current Microsoft 365 version. The mails are hosted on our Exchange 2016 server however I guess since this is happening in outlook before the mail was even send it is related to his outlook / office. The only issue that could be is that his mailbox size is too big and as most people don't work with a local PST archive, I would need to verify the current size of it but I assume it is above 3-6 GB at the moment. Some people have a mailbox size of more than 20 GB but this is the first time that I encounter such an issue and it is hard to find anything similar as all the search results end in tips or guide on how to set up an out of office.

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  • In order to confirm if the issue is related to your Outlook desktop client, it is suggested to try the reply test on your web mail and see if the issue could be reproduced. Besides, does this issue happen to emails from all the different senders?
    – Jeff Yang7
    Commented Nov 20, 2020 at 6:53

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I don't know if this will help but I set up a rule once so that all email I received from a certain person would return back to that person. I did this in hopes that person would stop emailing me with nonsense. It did work he stopped emailing me.

Try sending a new email to the person and not click on reply (all), if you are able to send a new email a rule might be set by that person to return all your Reply email back to you when you select Reply.

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  • That is not exactly what happened. He wants to reply to that mail properly to continue his work with that customer, business partner, whatever it was. It's not spam it is that he cannot reply to the mail directly by clicking on reply. Read through the example again, please.
    – VarmintLP
    Commented Nov 23, 2020 at 7:14
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Aside from rules, you should also check the message properties for this field:

enter image description here

And additionally, another possible source of control access is from Flow.

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  • Where can I find this? I'm always looking for something like this but I cannot find it. A simple right-click doesn't give me such an option and in the top bar I also couldn't find anything like that either.
    – VarmintLP
    Commented Nov 23, 2020 at 7:20
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    Go to File > Info > Properties for the above screen. Flow is located here.
    – Arctiic
    Commented Nov 23, 2020 at 8:26
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    I will add an update if we have this issue again, because it is impossible to find that one particular mail back @Arctiic
    – VarmintLP
    Commented Dec 2, 2020 at 15:25

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