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Hi @wALF - you can look into using some essential tools, like Litmus and Validity (ReturnPath) to track your structure and deliverability. Litmus will help you check different client renderings plus give you lots of advice on the structure of your emails and make suggestions on how to improve these.

ReturnPath allows you to send your emails to their seed lists to monitor how your emails are delivered and for some ESPs which folder your emails end up in. It will also tell you the % of emails that end up in Spam for each ESP. They also give you insights into your sending IPs and their general reputation and whether you are on any spam lists. They also have a few products that "validate" your sending reputation but I am unsure how much this really helps if you already have a good reputation.

Also check out registering with all the Feedback Loops to help you see when people are reporting your emails as spam: https://www.validity.com/what-is-a-feedback-loop/

You can register your sending IPs directly with Microsoft Smart Network Data Services to monitor your sends and reputation with your Microsoft (outlook.com & hotmail.com) targets. https://sendersupport.olc.protection.outlook.com/snds/

Cheers Darren