Outlook 2021 Configuration Problem with Two Outlook Email accounts

I use Outlook 2021 for email. I have two personal Outlook email accounts configured automatically to use MS Exchange e.g. name1@outlook.com (main MS account login) and name2@outlook.com.

I can receive mail from any external account and send mail to any external account using all my email accounts in Outlook 2021.

However, if I try to send an email from any of my email accounts in Outlook 2021 to my main MS account name1@outlook.com the message bounces and is not delivered. This behaviour is replicated across all my PCs. If I remove the second account name2@outlook.com then all works as expected. I tried to configure the account name2@outlook.com as an IMAP account but this doesn't work despite using the correct connection parameters.

I suspect this is an account configuration bug for Microsoft to fix when two personal MS Exchange accounts are configured in Outlook 2021. Any ideas?

You have two, identical threads!

Steve C said:

I suspect this is an account configuration bug for Microsoft to fix when two personal MS Exchange accounts are configured in Outlook 2021. Any ideas?

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I use Outlook 2016. I have two email accounts configured via Exchange and don't have the problem you're describing, so I don't think that's the cause. I don't have any suggestions for you though, sorry.

Victek said:

I use Outlook 2016. I have two email accounts configured via Exchange and don't have the problem you're describing, so I don't think that's the cause. I don't have any suggestions for you though, sorry.

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Thanks. I'm using MS Office Professional Plus 2021 so the software differs.

Steve C said:

Thanks. I'm using MS Office Professional Plus 2021 so the software differs.

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Valid point. I should also have mentioned that I have MS Office Professional Plus 2021 on one of my laptops with the same two Exchange email accounts, and they work together without issues.

I have an Outlook.com account that was supposed to replace my Hotmail.com account some time ago, instead they both have been merged into outlook.live.com and using the URL for either Outlook.com and Hotmail.com goes to the new one. The 2 accounts do use slightly different logins.

Victek said:

Valid point. I should also have mentioned that I have MS Office Professional Plus 2021 on one of my laptops with the same two Exchange email accounts, and they work together without issues.

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I can send emails between my two Outlook accounts. Any email sent from my Gmail account to my main Outlook account bounces unless the backup Outlook account is removed.

Steve C said:

I can send emails between my two Outlook accounts. Any email sent from my Gmail account to my main Outlook account bounces unless the backup Outlook account is removed.

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Well, this is surreal. I also get an "undeliverable" error when I try to send from my Gmail account to my main outlook.com account in Outlook. It says:

"None of our email accounts could send to this recipient"

However, I can send from Gmail to my secondary outlook.com account in Outlook. In other words, I can replicate exactly what you're seeing. I never noticed it before, as I have no reason to send email between those accounts. I have not tried removing the secondary exchange account to see what happens, but even if the problem goes away that's not a solution; I need the two exchange accounts. I poked around on the internet a little and have not found a solution yet.

Victek said:

Well, this is surreal. I also get an "undeliverable" error when I try to send from my Gmail account to my main outlook.com account in Outlook. It says:

"None of our email accounts could send to this recipient"

However, I can send from Gmail to my secondary outlook.com account in Outlook. In other words, I can replicate exactly what you're seeing. I never noticed it before, as I have no reason to send email between those accounts. I have not tried removing the secondary exchange account to see what happens, but even if the problem goes away that's not a solution; I need the two exchange accounts. I poked around on the internet a little and have not found a solution yet.

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Thanks for confirming what appears to be a bug. There is no real problem since all accounts will receive external mail - you can't send from a Gmail account to your main Outlook account.