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Android not reconnecting to proxy

Hi there,

I've recently been trying to setup my android devices to use a proxy. It works fine until I disconnect from WiFi and reconnect. Once I've done a disconnect/reconnect (disconnect either by disabling WiFi or going out of the wifi range) the proxy fails to reconnect. I have to completely disconnect the proxy by switching it to "none" save it, then reconnect by setting it up anew.

Any ideas as to why this would be happening? I have full control over the proxy server and can perform troubleshooting, but don't know where to start. I have a friend with an iPhone who doesn't have the same issue with the server, and another with an older version of Android OS without the issue.

The only thing I've been able to find by Googling is how to disable proxy, which isn't a solution.

Android version: 8.1.0
Network Impacting Apps: None
Rooted: Yes
 
Bump. Anyone have any ideas?

I've tested further on a brand new pixel 3 with stock OS, and I have the exact same issue. I don't know what to look at.
 
Does the proxy have an intervaling ip witch mean does the ip change everytime a disconnect happens based on your proxy server settings or is it a static ip that doesnt change?
 
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