Emails problems with Outlook

Makes an entertaining story in the pub, but not really seen in sophisticated or Organised Crime Gang behaviours.

Or even, in the original context of radical organisations. Those types realised years back that Smart Phones with encryption offered better security than basic 'burner' phones which agencies easily cracked. Then along came the Regulatory of Investigatory Powers Act 2000 (RIPA) in the UK so they turned to services like EncroChat - which was hacked by Security Agencies before the criminals realised leading to international arrests. The latest 'Ghost' encrypted comms channel was taken down by Europol 2 months ago.

Logging in to a single email account from multiple geographical locations will alert, even if using a VPN.

Email service providers (even free ones such as hotmail, which is now Outlook) will have AI or Machine Learning capabilities that will alert to this. Content of drafts, and the style or prose of content will be analysed and flagged. No same two people compose text in the same way. Mimecast & Abnormal have those features are two leading vendors who will more than likely used by the mail providers, afterall nobody is going to use their services if they facilitate spreading malicious content, viruses or whatever via their system so its in the providers interests to protect their users.

Basically, there are sophisticated commercial tools out there, I've used many if not most for this type of thing, but Government agencies have their own backdoors into security software which is why Kaspersky is banned in the US, as is TikTok - which IMHO is not far behind being banned in most countries, so nothing is invisible. That goes for all security software, not just Russian. Dont think the NSA, GCHQ, FSB etc are not listening, because they are.

Anyway, like I said it makes a good pub story, but not so real anymore

@Marklr did you get to the bottom of it? As suggested earlier it seems you inadvertly blocked the sender or the messages were falsely flagged as junk.
There are some very interesting 'capabilities' that the security agencies have these days. If you are flagged as a person of interest by one of those agencies, then you can pretty much guarantee everything you do will electronically will be at least collected on a server somewhere. It's nigh on impossible to sift through everything, but AI and keyword detection software is making it much easier to target data for analysis. Even commercial agencies are investing in these kinds of technologies to enable them to target their advertising better.

Basically, 'they' know EVERYTHING.
 
There are some very interesting 'capabilities' that the security agencies have these days. If you are flagged as a person of interest by one of those agencies, then you can pretty much guarantee everything you do will electronically will be at least collected on a server somewhere. It's nigh on impossible to sift through everything, but AI and keyword detection software is making it much easier to target data for analysis. Even commercial agencies are investing in these kinds of technologies to enable them to target their advertising better.

Basically, 'they' know EVERYTHING.
It's the Illuminati. They read EVERY email we send.
 

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