Dear Lil Lipsitz
Thank you for reaching out to the Microsoft Q&A forum. I understand you’re using Classic Outlook for Windows at home and messages aren’t sending, and you also want to contact Outlook online chat. I am happy to assist you.
To contact Outlook support, please:
- Visit Contact - Microsoft Support
- Type a brief description of your issue in the search box
- Scroll down to the bottom > select Sign in to contact support
- Log in to your personal Microsoft account.
- Under Products & Services, select "Other Products"; Under Categories, select a suitable Category.
- Click "Chat with a support agent in your web browser" (during business hours)
Thank you for your understanding.