Dear Shannon King1,
Thanks for choosing Microsoft Community.
Based on your descripion, I know the scenario you met. To better help you, first, could you please be kindly to provide me your outlook version? Since I found that this scenario always happens in Outlook 2010 and Outlook 2013. If you are using these two versions, please update your Outlook and then check the result.
If you are not using these two versions but still meet this, to narrow down the issue, could you please be kindly to log in your account in Outlook on the web and then try to set automatic replies on the web and check the result. You can click settings on the right corner of the Outlook Web>View all Outlook settings>Mail>Automatic Reply>And set here.
If you can set on the web, it means that your outlook has somthing wrong. For this, please be kindly to try the following suggestions and check if these can work.
- Just run the outlook client in safe mode:Open Outlook in safe mode
- Besides please also try to repair your office application: Repair an Office application
- Please also kindly try to create a new profile according to Create an Outlook profile.
Hope the suggestions above can help you. If this persists, please be kindly to provide me the screenshot (in private message) about your Outlook client by clicking File>Office Account>About Outlook. And if you cannot create on the web, please provide me the error page as well. I will continue to test for you and help you based on the information you provide. Your understanding and co-operation are highly appreciated. Note: For data privacy, kindly provide some above requested information in private message.
Here are the steps to open private messages:
To view private messaging options> click your profile picture at the top on the right > select the My Profile option.
I look forward to your next update in private message for further analysis. Thank you very much for your cooperation.
Thanks for your precious time. Have a nice day.
Sincerely,
Katherine