Hi all,

I'm having major issues with Hotmail/Outlook.com junking every single 
email (100% transactional) I send from my VPS ('Smartscreen blocked this 
email..') and is causing a headache in the form of customer 
complaints/support especially as the majority aren't technically 
inclined. I haven't had any issues whatsoever from any other major email 
providers and I only send a very low email volume (usually less than 500 
emails a month in total).

I've done everything I can think of to ensure I'm a reputable sender.. 
SPF/SenderID, DKIM and Reverse DNS all validate perfectly. Mail server 
uses an appropriate HELO, my IP is sparkly clean and not on any 
blacklists. Signed up to Hotmail complaints feedback loop, smart network 
data services, went through an automatic mitigation procedure which was 
apparently successful. The emails I send are mostly just plaintext 
alerts/receipts so there isn't really much I can do to make them look 
less 'spammy' and more 'hammy'.

I'm still dealing with Hotmail directly to find out what the problem is, 
but I was just wondering if anyone might have any suggestions? Have you 
experienced this? Perhaps I should just give up and relay mail via a 
high reputation ISP such as Amazon SES or something..

Cheers,
Luke

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