Run two web Apps in Debug Mode at the same time

Is it possible to do it ?
I am trying in different ports and in different paths but without success.

If you specify different ports, that should work. Try to take a look at the logs, to see if Xojo is giving any clue about what’s going on.

I do that all the time (different debug ports)

If you use different ports, then yes.

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Thanks to all that had answered this post.
In order to show the problem I am attaching an screenshot where you could see different debugging ports (8080 and 8081), two proyects open, one running in debug mode and when I try to run the second one, the message I receive

The XOJO IDE version used in this case is 2017 r.1 because they are old Web1 Applications. But same happened using newer XOJO versions.

I’m using mac, I can debug 2 or more webapps using Xojo2019r1.1 and newer (same Xojo or 2 different Xojo versions).

Sometimes I see that message but I just click ‘Hide’ when our webapp is big and have to connect to a database (not necessarily when running 2 debugs).

Edit: what happens if you press ‘Hide’ and open a browser to port 8080?

Nothing at all happened when pressing Hide…(the message hides)… So I open a new tab of the browser and try to run the second app at localhost and port 8081 and you could see below:

I’m sorry, I don’t know what to tell you.
I have used the different debug ports for years now without problems (on a mac):

The application executable names must be different! From the screenshot it looks like it could be two of the same project just different versions.

Thanks @AlbertoD
I tested in my Mac and works as you said

Could be the OS (Windows Server 2012R2) ?