Connection failures when using ChatGPT with Apple Intelligence on my iPhone 16 Pro

Hi everyone,


I’m having trouble using the Apple Intelligence app to ChatGPT on my iPhone. Every time I try to use it, the connection fails.

Here are some details that might be relevant:

- I have a private VPN (Pi with adguard home and some public dns servers) server located in Portugal, but I’m currently in Poland.

- I have completely disabled AdGuard, but the issue persists.

- I’ve seen reports of users with Surfshark VPN (NoBorders enabled) facing similar issues, but I don’t use Surfshark.

- I’ve tried changing the connection protocol, checking my DNS settings, and using different Wi-Fi networks and mobile data, but nothing has worked.

- I also reinstalled the app and checked for any configuration profiles or active VPNs that might interfere.

- My iOS is up to date.


Has anyone encountered this issue or has any ideas on what might be causing it? Any help is appreciated!



[Re-Titled by Moderator]

iPhone 16 Pro, iOS 18

Posted on Apr 4, 2025 8:54 AM

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Apr 4, 2025 9:09 AM in response to alexandre_martins

Many issues with ChatGPT and VPN's whether you are using Apple Intelligence or not. In fact many issues with VPN's in general. Once you remove the VPN, not just disable, and everything works OK, then you have identified the problem and you have the choice of not using the VPN or contacting the developer for a solution. It is the VPN's responsibility to make their service work for you, not Apple's responsibility to make the device work for a particular VPN.

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Apr 4, 2025 9:39 AM in response to alexandre_martins

Contact your VPN provider to see what "workaround" they may have for you. Any service that enforces geoblocking surely is not going to provide a workaround for the well known methods of VPN use to represent a different location that the service may consider to be fraudulent. Security is another issue where data is leaked to the VPN provider and that may not be acceptable.

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Apr 4, 2025 10:44 AM in response to alexandre_martins

alexandre_martins wrote:

I want a solution that works with my vpn!

Before you can do that, you need to find out if the VPN is even the problem. It may not be. But the only way to determine that is to try it without the VPN. I'm not saying never use the VPN again. I'm saying start the investigation.

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Apr 4, 2025 10:55 AM in response to IdrisSeabright

IdrisSeabright wrote:


alexandre_martins wrote:

I want a solution that works with my vpn!
Before you can do that, you need to find out if the VPN is even the problem. It may not be. But the only way to determine that is to try it without the VPN. I'm not saying never use the VPN again. I'm saying start the investigation.

I already tried without the vpn and it works. I also already checked the dns requests on the logs of my server to see if it was blocking anything and it wasn't, but i tried without the adguard, as i said in the beginning, and obtained the same result.

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Apr 4, 2025 10:58 AM in response to alexandre_martins

alexandre_martins wrote:

I already tried without the vpn and it works. I also already checked the dns requests on the logs of my server to see if it was blocking anything and it wasn't, but i tried without the adguard, as i said in the beginning, and obtained the same result.

Then, as everyone is telling you, it doesn't work with the VPN.


Why are you using the VPN? Are you using it to circumvent some sort of geographic restriction? It doesn't sound as if you're using it to log into an employer's secure server.

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Apr 4, 2025 11:15 AM in response to IdrisSeabright

IdrisSeabright wrote:


alexandre_martins wrote:

I already tried without the vpn and it works. I also already checked the dns requests on the logs of my server to see if it was blocking anything and it wasn't, but i tried without the adguard, as i said in the beginning, and obtained the same result.
Then, as everyone is telling you, it doesn't work with the VPN.

Why are you using the VPN? Are you using it to circumvent some sort of geographic restriction? It doesn't sound as if you're using it to log into an employer's secure server.

So my vpn is to access local services as plex, storage, ad guard, etc. I do it trough a vpn cause i don't want to open any ports to the public on my local network. I have to stay connected all the times cause i use it to access my dns service, as i said - to block ads and all.

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Apr 4, 2025 11:19 AM in response to alexandre_martins

Apparently, you're going to need to make a choice, the VPN or ChatGPT.


I suspect that the VPN doesn't improve your security nearly as much as you think it does. This article is mostly about commercial services, but it does describe some of the limitations and misconceptions about VPNs


Don't Use VPN Services

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Apr 4, 2025 11:33 AM in response to IdrisSeabright

We are talking about different things. My vpn is a tunnel to my local network; and it is self hosted - so it is not by any company, neither it is a commercial thing. I don't use it cause of the security, I use it cause i want to access my services when I am far from home.

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Apr 4, 2025 11:48 AM in response to alexandre_martins

alexandre_martins wrote:

We are talking about different things. My vpn is a tunnel to my local network; and it is self hosted - so it is not by any company, neither it is a commercial thing.

I understand that.

I don't use it cause of the security, I use it cause i want to access my services when I am far from home.

Again, it appears that you will have to chose whether to use the VPN or ChatGPT.


You should be able to use ChatGPT on your iPhone if you turn off WiFi and use cellular data.

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Connection failures when using ChatGPT with Apple Intelligence on my iPhone 16 Pro

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