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iCloud SMTP Issues

NOOB to Sophos XG.

It appears that I cannot use Apple's iCloud to send emails. I'm not having any issues with receiving emails to my iCloud accounts, nor am I having issues sending or receiving with Gmail. When I try to send using iCloud, I get the following error in Apple Mail and am unable to change the setting in MacOS 12.2.1:

I have the firewall email setting in Legacy mode, with the following SMTP TLS Configuration:

However, I've seen others note that the issue is a DNS issue, but none note the solution. Can someone give the solution publicly?

Thank you in advance.

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0 rfcat_vk over 3 years ago

What is your firewall rule fro SMTP?

Ian

XG115W - v19.5.1 mr-1 - Home

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0 Sophos User5846 over 3 years ago in reply to rfcat_vk

Sorry, a bit of a NOOB. This what you mean?

Note that I'm not having issues with Gmail, which appears to rely on IMAP for sending and receiving., whereas iCloud only used it for receiving (which is working).
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0 rfcat_vk over 3 years ago in reply to Sophos User5846

***,

to improve your security a little, change your destination zone to WAN from ANY.

What about the result of the rule>

Ian

XG115W - v19.5.1 mr-1 - Home

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0 Sophos User5846 over 3 years ago in reply to rfcat_vk

Thank you, definitely open to suggestions! Made that change. Here's all of the rule:
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0 rfcat_vk over 3 years ago in reply to Sophos User5846

Hi,

I have found the scan SMTP traffic is not reliable if you are using SSL/TLS scanning, try turning on the DPI, but ultimately I enabled the web proxy even though it does not scan any traffic and my ISP SMTP servers CAs are not recognised as valid by the XG so ultmately I have to trust the outgoing mail is okay..

Ian

XG115W - v19.5.1 mr-1 - Home

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0 Sophos User5846 over 3 years ago in reply to rfcat_vk

DPI was already on, so that definitely didn't solve it. How did you go about setting up an SMTP proxy?

There appears to have been a thread on setting it up from a couple years back, but the screenshots are now gone.
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0 rfcat_vk over 3 years ago in reply to Sophos User5846

Hi,

I gave up because of issues with the XG and the CAs on mail servers on two different ISPs mail accounts. I don't scan smtp/s and have to trust the on user machines anti-whatever for protection.

One ISP )RSP) has a CA which has about 20 of the company websites in it and the XG reports the name is not the same, this company has many many mail customers so I would suspect there is an issue with the CA scanning on the XG, but how to prove it?

Ian

XG115W - v19.5.1 mr-1 - Home

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0 Sophos User5846 over 3 years ago in reply to rfcat_vk

How did you go about setting up the SMTP proxy? All the documentation I'm finding is for UTM, and doesn't appear to apply in XG.

Again, thank you for the patience and assistance.
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0 Sophos User5846 over 3 years ago in reply to Sophos User5846

This is strange. I installed Outlook and set up iCloud there using an app password. Sending and receiving mail works without issue, so it's definitely something to do with how Apple Mail sets up the SMTP connection, as it doesn't require an app-specific password.
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0 rfcat_vk over 3 years ago in reply to Sophos User5846

Hi,

my wife uses outlook as well as mac mail, I don't like the new outlook I have had to revert to legacy mode to be able to configure email accounts. The new version locks sending details on the assumption they are the same as the receiving details and uses the wrong ports.

Ian

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iCloud SMTP Issues

Submitted a Tech Support Case lately from the Support Portal?