Hi @Megan Dyson ,
error message for one of the accounts (three are loaded) reads we are unable to connect right5 now
When did this issue happen(first configure your account, send/receive message after you configured your account, or when you activate Outlook 365 with your account)
What's the type of your account that got error message? Did it have any differences with other loaded accounts ?
For this error, if it occurred on your first configuration, in order to avoid the interference of Internet, it's suggested to first close your VPN or switch to other Internet to check if the issue has any difference.
Also, based on my research, the issue may also be related to if we have enabled ActiveProbing, we could check and modify it in register editor(please remember to Run as administrator, and serious problems can occur if you modify the registry incorrectly. Before making changes, back up the registry to restore it in case something goes wrong.):
[HKEY_LOCAL_MACHINE \ SYSTEM \ CurrentControlSet \ services \ NlaSvc \ Parameters \ Internet]
“ EnableActiveProbing” = dword:00000001
if these accounts all have already been configured on your Outlook and the issue only occurred recently, have you performed any special operations before it? In order to avoid the interference of add-ins, it's suggested to restart your Outlook in safe mode to check if the issue has any difference(Windows + R> type "Outlook.exe /safe" > Enter).
If it's invalid or that are not your case, please provide me with more information about your issue and I would continue to research it with you.
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