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.
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