iMessage stops working when on VPN but works on 3g or wifi?

Hi there. Any workaround to make this work? it is clear the TCP port 5223 thing but interestingly ALL other messaging apps works (WhatsApp, Skype, Yahoo, Google Hangout) but not iMessage... perhaps Apple can enhance how iMessage use underlaying IP network management?

Thanks

-f

I can say that this happens to me as well on several different VPN's I have setup including different vendors. It is a restriction Apple seems to set, and possibly knows location by your phone which then denies the connection after connecting VPN. This is absurd and Apple should for sure fix this! You can connect a laptop and use Full VPN without any issues or restrictions!

Hi,

Since at least iChat 3 and certainly using Internet Sharing in Leopard (iChat 4.0.x) there has been an issue with two connections to the Internet.

Is the VPN the only connection ?

10:00 pm Monday; November 16, 2015

Hi,

I am still not sure from the 10.33 post (the local time I see) whether you have just the VPN or whether there is still another Internet connection going on ?

The Issue in Leopard was if a Leopard computer had Internet Sharing turned ON then the computer that was doing the Sharing could see both the Internet connection it was given but Failed chats in iChat also reported the Originating Mac's IP address.

Moving to your Last Post there is Location checks.

iMessages Account is set to your Location.

in Mavericks and Yosemite that is set in the Details button in Messages > Preferences > Accounts > iMessages account and the Details Button.

You have to Sign In here to view the details.

AS a security check this detail is checked against the IP that your location appears to be at.

AS the Location and IP's location may not match then the iMessages server will not let you login. (you look like someone pretending to be you).

It also messes with Time Stamps (and the Login is Time Stamped) which means even if you do manage to Login you may miss some iMessages because of time differences between the VPN's Location and the Mac's.

If the iMessages servers see this sort of behaviour then it will block the Apple ID for that Mac.

That is to say the iPhone should still see sync copies of iMessages sent to the Apple ID but the Mac will not.

Nor can the Mac send as it cannot login.

The only way to resolve that is to Contact Apple Support and move up to a Level 2 person and ask them to reset it.

However it is not that simple as the Upgrade from Yosemite to El Capitan is also triggering this from some people and the Level 2 people involve the Engineers who are looking for the Trigger.

You have an Apple ID issue which are free to fix. (Level 1 people are Script Led looking to solve Apple Care Hardware and Software issues).

8:17 pm Tuesday; November 17, 2015

Hi,

iMessages logs in on both port 443 and 80 to confirm your ID (80) and the fact it is used on iMessages Server (443)

The 5223 only confirms that your Contacts are also registered on iMessages.

The Login uses the ID and password and the Serial Number of the device.

This is a security feature and is designed to make sure the Login is "you".

It is likely the iMessages server will reject anything that looks like it is trying to circumvent that.

If you do get locked out of the iMessages server it is a tortuous phone call to Apple Care to get it sorted.

8:59 pm Monday; July 25, 2016

i am a iPhone user and set up my own OpenVPN server. I am having the same issue. Does anyone know what setting or issues that I should look at as the VPN provider and user?

Could be your VPN supplier is blocking the port the iMessage uses (5223??) and their support folks don't know it.

Could be that Apple's iMessage servers are blocking your VPN server's addresses for some reason. (VPN servers tend to get blocked because all sorts of people use them for all sorts of purposes good and bad.)

Other than asking Apple Support about your specific VPN supplier and asking your VPN supplier again about the iMessage port, Linc's answers seems to be a practical one.

The problem is being caused by the VPN (or, more accurately, the host network that the VPN is connected to). There is nothing we can do about that. Talk to the administrators of the network and the VPN. This is NOT an Apple problem, it's a network problem.

The issue, which is on my iPhone, has SMS so the message fails the first time then when I hit resend it sends it over cellular (green SMS). I am on VPN over wifi. If I turn the VPN off, it works fine on the same wifi. On the MacBook, it automatically just sends it green through the phone.

Is that what you were looking for? I am using OpenVPN.

Why are you using the VPN in the first place?

iMessages are fully encrypted. There is no need to connect to a secure network to send iMessages. There may very well be a conflict based on the location of the device as reported by location services and the location of the originating IP address for the message, which would be the address of the VPN gateway to the outside world, which is in a different physical location. Or, it may be one of the other reasons already suggested. Blocked port, blocked VPN gateway, etc.

i use the VPN to encrypt the other things, like browsing, that I do on public insecure networks like airports, coffee shops, etc. it really is not convenient to switch between the VPN on and off for iMessages

I Have opened up port 5223/tcp on the server as well as 80 and 443 are open. no luck, same issue. any other suggestions? Anything to fix the location thing?

Opening up 5223 tcp on the server made it work different. I seem see when someone is typing and now but people say it tries as a iMessage then fails and sends as SMS. send is the sane It tries every time to send iMessage like it thinks it should but then fails when it tries.... I also disabled the firewall on the server completely and does the same thing. Maybe an OpenVPN thing or something with the location issue? It's a new server so I can't imagine Apple has banned me

What should we do?

Either disconnect from the VPN when you want to use iMessage, or try another VPN service.

Just connect all of your devices to the vpn and make sure de port 5223 its open, reset the imessage app in all of your connected devices.

Thats how i fix the problem and i use openvpn as.