Hi @Zac Avramides ,
From the description, do you mean the issue is that the Outlook desktop client fails to reconnect automatically and cannot be reopened after network drops?
Is this a recently occurred issue? If so, have you made any changes on either Outlook or Windows OS right prior to the issue?
What's the detailed build number of the Outlook client? You can view the version information via File > Office Account > About Outlook.
Besides, in order to eliminate whether it's an issue with any background services or programing, it's recommended to try performing a clean boot in Windows and check the result.
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