Outlook not sending to certain domains

Tumi Masemola 0 Reputation points
2023-02-20T15:01:00.2133333+00:00

Good Day

I have a strange issue here. We have an on Premises Exchange Server 2019 and users on Office 2016, 2019 and 2022. Some users can't send emails to certain external domains, it brings out an error that the email address doesn't exist. But if they send to the same email address using their Phones or OWA, the email goes through and is received by the recipient.

Please help with some ideas here. Thank You.

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Exchange Server
A family of Microsoft client/server messaging and collaboration software.
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Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
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  1. Andy David - MVP 153.9K Reputation points MVP
    2023-02-20T15:49:31.33+00:00

    Sounds like cached entries in Outlook perhaps.

    Consider testing with a user and deleting the cached entry in Outlook and re-sendind

    https://learn.microsoft.com/en-us/outlook/troubleshoot/contacts/information-about-the-outlook-autocomplete-list#remove-autocomplete-list-entries-one-at-a-time

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