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For security reason, Microsoft has deprecated the use of SHA-1. 
For more information, see Microsoft Teams installations on a Mac.
Starting with Version 16.21, Microsoft Teams will be installed by default for new installations if you're using the Office suite install package. This appears to have been an issue a year or two ago, but I'm a little stuck. We are not in an Exchange hybrid setup of Office 365 and Exchange 2010.Ĭurrently, working with Exchange admin and reading the links below. If we use OWA in Safari, similar issue with attachments. Downgraded to older Outlook didn't help (I tried version 16.48). Deleting the profile and creating a new one does not help. By deleting the email with the attachment, emails roll back in. 
The Outlook Client stops talking to the Exchange server and users don't get any email it appears to be trying to sync the attachment by uploading it to the Exchange server. But when you attach any kind of file, Outlook is hosed and we get an "Operation on the server timed out" message. Affected Users are on Big Sur 11.6.1 + Outlook 2019 (16.54).I'll post the specs below and the things I've tried. We're having an odd issue where users can't send attachments in the Outlook client.
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