I had the same experience with outlook.com and servers hosted by many cloud 
providers, including Linode.

The solution with Linode is very simple, just open a ticket and they'll get in 
touch with M$ and you'll be added into their whitelist. It usually takes 2 
business days.

Just make sure to have proper/valid SPF records and rDNS.



On Mon, 6 Dec 2021 20:42:11 +0100 Daniele Nicolodi via mailop 
<mailop@mailop.org> wrote:

> Hello,
> 
> is outlook.com blocking all Linode IPv4 space or am I just unlucky?
> 
> >     eur.olc.protection.outlook.com[104.47.18.225] said: 550 5.7.1
> >     Unfortunately, messages from [109.74.203.128] weren't sent. Please 
> > contact
> >     your Internet service provider since part of their network is on our 
> > block
> >     list (S3140). You can also refer your provider to
> >     http://mail.live.com/mail/troubleshooting.aspx#errors.
> >     [VI1EUR06FT017.eop-eur06.prod.protection.outlook.com] (in reply to MAIL
> >     FROM command)  
> 
> What is a good neighborhood to park a mail server these days?
> 
> Cheers,
> Dan
> 
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