Website timeout, but only on mobile devices - IIS - iis

I am trying to test a website on mobile devices, but I keep getting timeouts on Android (using Chrome) and iOS tablets and smartphones (using Safari). My Windows tablet and a separate Windows PC (both using Chrome) work fine. Here is my network setup. It's a little convoluted, but blame COVID-19 and working remotely for that.
Web Application: DotNetNuke running on IIS using dedicated MSSQL database to store user account information and localization settings.
Web Server: Windows 10 running a local MSSQL web server database and IIS. Connected Wireless to my internal network. Using a VPN client to connect to the Rest API within my work network to access the core application server. The web server has a self-signed, untrusted certificate.
Windows PC: Windows 10 laptop connected via wire to the network. Certificate error is ignored by the user in Chrome and the webpage comes up.
Windows Tablet: HP tablet running Windows 10 connected wireless to my network. Certificate error is ignored by the user in Chrome and the webpage comes up.
Android Phone: Google Pixel 3 connected via WiFi to my network. Using Chrome, connection times out.
I've try a couple of Android devices and an iPhone, and neither connect. I'm not sure where to begin debugging this. I know it worked last week because I tested the configuration to prepare for testing this week. Any blaring issues to look at, other than perhaps a code change that broke the mobile rendering?

What is the way of your Windows Tablet connected the network? Is the wireless connected way the same to Android Phone? in other words, using WiFi too?
I doubt if your Wifi network works like before. Check your IP of the Android Phone, then Ping the IP on the webserver, and confirm whether the network with the target web server is unobstructed.
Alternatively, we Ping the gateway of the network on both an Android phone and the website.
About the Ping Tool in Android phone.
https://www.makeuseof.com/tag/android-networking-apps/
Feel free to let me know if there is anything I can help with.

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Refer to image below and for more details check out the insightful medium blog by Neeraj Moudgil
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