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I can't help feeling we've been duped

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Could it be something specific to the Windows world? I checked the validity of the rule in Little Snitch by trying to reach sync.1rx.io from Firefox, and the connection is blocked by LS. So the rule is working here, but it is not triggered by enpass, which tends to indicate that enpass is not trying to connect to sync.1rx.io, at least on my Mac. Are you 100% sure AdGuard was triggered by enpass?
We may get more insight from the Enpass staff.

It appeared to be Enpass. My understanding of the windows pop up ad stuff is that there are providers of the ads that have more concern over their profits than the safety of the users that are victims of this garbage. Enpass might not intend for unsafe ads to be shown, but their ad provider might do it anyway.

Enpass may have decided that the lifetime license stuff was costing them too much, so they decided to pad their revenue with this junk.

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