@David Kafrissen
Whether those shared mailboxes are also migrated to Exchange online? I test it in my lab, after adding permission, I wait about 30 minutes before this shared mailbox shows in Outlook (Run in Online mode). So, I would suggest you switch Outlook to Online mode, then wait for a while to sync.
You can also add an Exchange online created shared mailbox to compare, check whether this Exchange online created shared mailbox could show in Outlook.
If this Exchange online created shared mailbox has shown in Outlook, but the migrated shared mailbox still not show up. You could try to configure it as a separate account:
Use the Shared mailbox email address to configure Outlook profile:
About the Account and Password, you need to use the credential which has full access permission to this shared mailbox:
In this way, you could configure shared mailbox in Outlook without wait.
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