Advisory: Sophos Endpoint "Your connection isn't private" after reboot. Policy settings can be returned to normal. See: KB-000045954 for the latest updates.

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Push/Portal Encryption Password Reset Loop of Death

Love Sophos Products and glad to be a partner. However, one product that I wish would work well does not and that is Secure Email  (push/portal) encryption. In particular the password reset for users outside your organization is flawed and creates a loop at least at this point in time (Full disclosure I do have a case open but though I would post here just in case). Additional Note: we use both push and portal encryption via two separate Secure Message policies.

It appears that Portal encryption passwords set by a user outside your organization (someone who is in receipt of an encrypted password from one of your employees) cannot be reset via the password link in the email unless they know secure questions that were never asked when they setup the Portal access. 

Also, seems to be that push encryption email passwords are completely different than portal encryption email passwords UNLESSS you need to do a password reset. This is causing all kinds of issues and users calling in that their recipients can't open encrypted emails (the problem snowballs as time goes on). The Big issue is I can't do anything about it except call Sophos for EVREY external user where a users forgot their password and it won't let them reset. Additionally if I move users to Portal Encryption I can't seem to get Sophos to recognize the the credentials for Portal are different and not connect to push credentials. 

I really want this product to work but honestly we might have to drop email security offering. However, having it all under one portal is ideal and would rather the Encryption product improve. 

Anyone else having issues with Push/Portal Encryption password resets or am I a lone wolf? I know this is a tricky and complicated topic but worth a post. 

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