Sounds like cached entries in Outlook perhaps.
Consider testing with a user and deleting the cached entry in Outlook and re-sendind
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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.
Sounds like cached entries in Outlook perhaps.
Consider testing with a user and deleting the cached entry in Outlook and re-sendind