macOS Big Sur Little Snitch 5 Network Module Conflicting With Adguard's Module, Mail SMTP Timing Out

[XxUnkn0wnxX]

The issue is that Adguards network extension is clashing with little snitches network Extention, even turning off little snitch's monitor does not fix it. if I remove little snitch from network settings it works just fine, but then I need to reboot to enable little snitch again so it re-installs the profile into the network settings.

if I disable adguard mail SMTP works fine, disabling rules or any other settings within adguard does not mitigate the issue, only if I use proxy mode instead of the network module.

also, unticking mail in applications does not fix the issue.

Steps to reproduce

install little snitch 5.0.2 & have it running
make sure it looks like this in your network settings:

then open mail & make sure you have icloud setup
go Window --> Connection Doctor

Expected behavior

icloud SMTP to connect without issues.

Actual behavior

icloud SMTP keeps timing out:

Customer ID

I didn't get an auto-reply, but I included the issue ID in the message I sent with the report.

Your environment

• Environment name and version: macOS Big Sur, Apple Mail App
• Any specific potentially conflicting software installed: Little Snitch 5.02

[Eugene-Savenko]

HeldDesk ID: 3017724

[Chinaski1]

Hello there!

To troubleshoot this issue, we need to get the app logs.

Here's what we need you to do:

1. Menu -> Gear -> Advanced -> Logging level -> Debug;
2. Reproduce the issue (and remember the exact time when it happened);
3. Menu -> Advanced -> Export Logs and System Info...;
4. Send the archive to apple@adguard.com and mention this issue number in the subject.

[XxUnkn0wnxX]

email sent...

[XxUnkn0wnxX]

after sending the logs, I took a look at the smtp logs for iCloud & it uses the domain p47-smtp.mail.me.com with the port 587.

I added that in the advanced settings

& the issue has resolved while using the network extension. with little snitch active

also when I removed the new changes I added, the issue does not occur anymore so I'm not sure what happened. maybe after upgrading to big sur without doing a clean install of adguard the settings did not persist until re-applying them?

[sfionov]

Reported incompatibility with LittleSwitch to Apple:
FB8918126
https://developer.apple.com/forums/thread/667962

[Chinaski1]

Good news everyone.

Looks like the recently released update of macOS solves this issue.

• In order to download the current beta version, you need to join the Apple Beta Software Program: https://beta.apple.com/