Hi @David Ewer ,
For Question One:
Outlook is prompting to me to sign in to activate.
Does this activation prompt issue only exist in Outlook? Will you receive the same prompt when using other Office programs? You could check your activation status via File > Office Account. About Office activate issue, please check:
Activate Office
Office repeatedly prompts you to activate on a new PC
For Question Two:
Outlook is also asking for a password for my mailbox.
What's the version of your Outlook? (File > Office Account > About Outlook). Please make sure you have upgraded your Outlook to the latest version.
What's the type of your account? POP, IMAP or Exchange?
In order to exclude some other factors as much as possible, I would suggest you to try to reset your Outlook-related registry keys to restore Outlook to its original state. Please check the steps below:
- Exit Outlook and open the Registry Editor
- Navigate to: HKEY_CURRENT_USER\Software\Microsoft\Office\16.0
- Right-click the Outlook folder
- Rename it as Outlook1
- Restart your Outlook and add your email account to test
(Note: 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.)
If the password prompt issue still continues then. As I know, for Exchange email account, windows usually will cache its password to Windows Credential Manager. And problems with the password cache may cause this kind of prompt issue. So, please try to clear out the Outlook related credentials and see if it works: Control Panel > Credential Manager > Windows Credentials > Locate the set of credentials that has your email account in the name > Expand and click Delete> Restart Outlook Client and re-enter the password.
Here is some more troubleshooting methods about password prompt issue, for your reference: Why does Outlook keep prompting for password.
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