Using Classic Outlook on Windows for personal email, calendar, and contact management
Hello Nicholas Aldridge (NA),
Have a good day. Thanks for your post in forum.
Regarding your description, kindly try to fix the issue of Outlook with using Service and Recovery Assistant tool and check the issue. Following are the steps for fixing the issue of Outlook.
Download and start Support and Recovery Assistant
1. Go to the Support and Recovery Assistant for Office 365 download page.
2. Click Download now.
3. Run the installation program.
4. After installation, Support and Recovery Assistant will start automatically.
Use Support and Recovery Assistant
1. Choose I agree to accept the license agreement.
2. Select the app you want to get help with, and choose Next.
3. Select the support topic that best describes your issue, and then choose Next.
4. Sign in with your work or school account.
5. Wait for the series of tests to finish.
6. Review the test results, and do one of the following.
· If the application succeeds in fixing your problem, follow the prompts and close the tool.
· If the tests fail, the application will let you know the reason and suggest other solutions.
If the issue still persist, I need to collect below information from you.
1. Kindly provide us your detailed screenshot of your Office and Outlook desktop client version. For knowing Office and outlook version https://support.office.com/en-us/article/what-version-of-outlook-do-i-have-b3a9568c-edb5-42b9-9825-d48d82b2257c
2. Does other office application have the same problem?
Hopefully above information will help you.
Regards,
Darpan