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Scan IMAPS & SMTPS issues with Apple Mail

I've been running with SSL/TLS decryption and scanning disabled for several months based on issues it was causing with Apple Mail. This was a known issue that was supposedly fixed in Sophos XG 18.0.1. I just enabled it again hoping it would be fixed but I'm still having issues where it will not connect via IMAPS or SMTPS. Sometimes it will work on my iOS devices but on my Apple iMac using the Mail app, it seems to be completely broken.

I do have the Sophos certificates installed as root (I have no issues browsing the web or making HTTPS connections) on all my devices and I'm running Sophos XG 18.0.3.

Anyone else running IMAPS and SMTPS scanning without issues in Apple Mail?

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0 rfcat_vk over 3 years ago

Hi,

smtps scanning works with Mac mail on my Mac mini running big sur. IMaps does not work and is supposedly fixed in mr-4 maybe mr-5.

the dpi engine breaks all mail scanning regardless of application.

ian

XG115W - v20.0.2 MR-2 - Home

XG on VM 8 - v21 GA

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0 shred over 3 years ago in reply to rfcat_vk

That's frustrating it's still an issue. I'm also on Big Sur.

It seems to work fine on my laptop with Ubuntu 20.04 using Thunderbird, both IMAPS and SMTPS.

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Sophos XG guides for home users: https://shred086.wordpress.com/
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0 shred over 3 years ago in reply to rfcat_vk

That's frustrating it's still an issue. I'm also on Big Sur.

It seems to work fine on my laptop with Ubuntu 20.04 using Thunderbird, both IMAPS and SMTPS.

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Sophos XG guides for home users: https://shred086.wordpress.com/
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0 rfcat_vk over 3 years ago in reply to shred

Hi Shred,

there is an outstanding NUC or whatever for the issue. When the next fix is released I will try again with my iPhone and iPad. As I advised SMTPS scanning works on mac mini, iPhone and iPad and also my wife's 2014 MBP running Big Sur just not iMaps. You can configure the XG to do the scanning and the mac mail works for about 30 minutes then throws up trust errors and on DPI just breaks all mail connections.

Ian

Like you, I have no problems with https scanning and decrypt functions, though on the iPhone and iPad I ave had to create exceptions for some strange reason the apps work in the mini but not on the IOS devices.

XG115W - v20.0.2 MR-2 - Home

XG on VM 8 - v21 GA

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