Can you share a screenshot of the error for the Assistant you're seeing? 

In the meantime, what's your question? Someone on the community might be able to point you in the right direction. 

I tried just for you.  No problem getting through to an "Expert".  Honestly, I am impressed how fast I got connected, probably within 1 minute, almost without any wait time.

The unfortunate thing is, no one here will be able to tell you why.  It's just that this is not a problem others are reporting and it'd look like this is an isolated problem related to your network/computer/security setup.

Did you try using a different machine with a different setup or on a different platform?  This could give you a clue what may be causing that.  If you still have problems, you will need to have an IT person diagnose for you locally - this is generally not something Intuit will support.

Good luck.

ITO Chat still not working… tried iPhone on cellular, no go. Removed all Comcast advanced security, no go. iPhone on cellular has no Norton antivirus & no vpn. Setting on Safari on cell allowed all cookies and other security protocols - still not working. 1-800 ITO help was no help. Still doesn’t work.

Chat still not working. Going to have to CALL for help every time. Very strange. Many years with ITO and no problems. I see another user with same problem. He said 1-866# advised many users having same problem with chat. When is intuit going to help?

@garland I'll follow up for more information in a private message.