VPN not working on Windows 10 1903

You are right  It is typical Microsoft Shoddy Quality Control for Business Customers. 

FYI, I just installed a.clean copy of 1903 and for some reason my saved VPN credentials still work from System tray.  In fact, even on my upgraded machine from 1803 to 1903 if I create new VPN and save the credentials, the connection works from the system!  I am not sure why yours is not working. 

One more thing I notice is that when it does not connect, the event viewer does not record anything either?!

I'm a developer as well as an IT director, so I'm half-tempted to attached a debugger to the tray on one of these boxes that don't work around here. But, I'm pretty sure that the reason it doesn't throw any event errors is that the tray is nothing more than a dumb call to the actual API and they missed/forgot to update/added a dependency that the tray calls. Since the call never actually makes it through, the API doesn't actually do anything and hence, no logging of any sort. 

I just BSOD'd a box poking the driver structure and after reboot...now the connections work from the tray on that box??! Hmm. 

Yeah, I love how each an every release they jump through hoops to make stupid little GUI things "better", check like crazy to be sure gaming features work, and add useless visual features, but never take the time to validate features like VPNs, domain functions, and other business features.

Well this has happend to me also after the windows 10 1903 update june 2019.

Home VPN connects to my server SSTP. 

When you try connect from bottom right and connect to my VPN, it stays on the 'Connecting to...' and doesnt budge. If you goto network and internet settings and choose VPN and connect there, it connects but the settings must be different because I loose internet but connect to my network.

So because this has been happening after this update, it must be the cause! Other people have reported similar and also different problems to mine.

I have removed vpn and set up again from scratch. Checked firewall and has this 443 port open and allowed and set up for my policies remote users, computers etc.

So a fix is needed. I removed the old windows installation when I updated. Stupid me eh? Im gonna try a restore?? Probably will not work.

Bloody typical!

I use SSL VPN connection. Not sure if others have different issues due to their VPN type i.e L2TP or IKEV2.

EDIT: I can ping my server name and IP address so there is a connection going through at both ends! Remote desktop works without VPN because Im on the same network at home.

POSSIBLE FIX:

I today ran updates again and found a net framework cumulative update and adobe flash update. I checked and now I can connect with no issues. So maybe run updates again after 1903 and maybe could be a fix something to do with NET framework?

NOPE CAN ONLY CONNECT VIA CONTROL PANEL BUT NOW HAVE INTERNET WORKING AS WELL. UH!

Just to higlight what I did for a fix which worked for me.

After installing the 1903 update, run updates again and install this: 

https://support.microsoft.com/en-us/help/4495620/may-14-2019-kb4495620-cumulative-update-for-net-framework

I did this and now is working fine. Im connecting VPN SSTP to my home Domain as well.

Let me know if this works for you?

I tried those and can still only connect through settings. I have a bunch of users I have to alert to not update or lose the taskbar VPN connection. The settings connection is not a valid solution for those not tech savvy. This really needs to be addressed with a hotfix.