API-Login-to-TWS-Requires-2-WL-Restarts

That's not right. If TWS restarts, it's possible, albeit unlikely, that Wealth-Lab may reconnect without doing anything.

However, with TWS running and following a Wealth-Lab restart, any action to connect to TWS (click Order Mgr > Connect, request data, etc.) will result in an immediate connect, every time in my experience.

Not for me. The orders page indicates it is connected to IB, but the account number does not appear and cannot be selected (greyed out). That's the tip-off that it didn't really connect. The accounts page will not show the account values either. One more restart and we're off to the races.

100% repeatable now.

BTW, using the Connect button on the Orders page to connect has *never* worked for me. It responds with a "Failed to Connect" message every time.

Do this.
1. Close everything.
2. Start TWS
3. Start Wealth-Lab
4. Order Manager > IB > Connect

Assuming the configuration is correct, I'd eat the next plate of monkey brains someone serves me if that doesn't result in a successful connection.

When I follow those instructions, I get an "Interactive Brokers Connect Failed" message in red and black. Green Connect button goes back on. If I try again, I get same result.

BTW, I can connect with TDA or Tradier account every time using your sequence.

I restarted WL again, and it connected fine. Thus, the title of this post.

I'd like to meet with you on zoom to get to the bottom of it. There must be something else in the mix on your machine because it's really unthinkable that it doesn't work every time, immediately, which has been my experience for years.