VPN seems to be blocking messages sent via SMTP on iOS/iPadOS
After the VPNs on four Apple devices (iOS 18.1 and iPadOS 18.1] was updated to 2.3.4.2 (b), I’ve noticed that emails from the standard Apple email app, are not being sent while the VPN is active.
The message remain in the Outbox and after some time I get a dialog thus: “Cannot Connect to the Outgoing Mail Server for <mymailacct> / Mail can try to repair these settings.” And then, if I cancel this message, I get a further message “Cannot Send Mail // The connection to the outgoing server // "<mymailacct>" failed. // Additional Outgoing Mail // Servers can be configured for Mail accounts in Settings > // Apps > Mail > Accounts. // Operation timed out”
If I turn off the VPN the held emails are then sent, as are any new ones I create. Once the VPN is back on, any new messages are again blocked.
This occurs for a number of email accounts from different providers each of which use SMTP servers to send email. However a mail account provided by a school (which I think use a Microsoft exchange system or the like) is unaffected.
The VPNs are set up to use the Automatic protocol; I don’t know which one is being used, but I note that the Hydra protocol has disappeared. I I’ve deleted and reset the VPN configurations but this hasn’t made a difference to being able to send SMTP emails when the VPN is active.
Any help appreciated. Best wishes, Stefan
PS: we still have the Mobile Security app installed. Not sure if it’s necessary or how it might interwork with the new VPN.
Answers
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Hello.
Check out these articles:
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and see if the steps in the articles will help you.
Regards.0 -
Hi Gjoski
Thankyou for your reply.
I found that changing the location of the server to which my VPN connects provided a workaround. I should have said that I'm in the UK. Amusingly, I found that changing the location to France worked first; then I noticed in the UK we have a choice of servers in four cities (London, Manchester, Glasgow, and Birmingham). Interestingly, I found that specifcally setting the location to Birmingham or Glasgow works, but setting it to either London or Manchester doesn't.
NB: I am a little concerened about the suggestion to use Split Tunnelling to address an issue with email sent over SMTP - it's my understanding that SMTP mail can be insecure (especially over public Wi-Fi) and one of the reasons I use a VPN when travelling is to avoid being snooped upon.
Anyway, thank you for helping me find a workaround. It's just strange that until recently I have either been lucky in that the Automatic location selection for me has picked servers in one of the cities that work (Birmingham and Glasgow) or that something has changed to cause various SMTP servers to now blacklist the IP address ranges allocated (to me at least) in London and Manchester.
Best wishes, Stefan
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