First, do you really need a secure site in dev environement?
If it was working without the serverentry prior to the problem, then you technically don't need it.
To check what's going on, run the command:
herd secured
You should see something like this:
+----------------------------+----------------------------+
| Site | Valid Until |
+----------------------------+----------------------------+
| expose.dev.test | 2024-08-10 12:07:38 GMT |
| herd-templates.test | 2024-09-05 25:12:77 GMT |
| reverb-110.test | 2024-09-11 13:44:56 GMT |
| tinkerwell.app.test | 2024-10-16 19:53:32 GMT |
+----------------------------+----------------------------+
What you can try to do is unsecure the site that gives you problems:
herd unsecure example-site
Double check herd securedto be sure the site is no longer there, then herd secure example-site and finally:
php artisan cache:clear
php artisan config:clear
php artisan route:clear
php artisan view:clear