From someone else with similar experience: I've been following all best practices to the best of my abilities (rDNS/DMARC/DKIM/SPF/etc). After all that was properly in place, the only problematic receiver was Microsoft (outlook.com/hotmail.com/live.com), which bounced and provided an appeal process.
I filled the form, was requested documentation from my ISP on the IP address.
I asked my VPS hosting company (since they provide the public IP and therefore act as ISP) and they proactively reached out to Microsoft, who lifted the restriction after that.
So since then no delivery issues. YMMV.
If you intend to host this from your residential address, it can be a good idea to tunnel external traffic over VPN through a VPS or similar. Not only for privacy reasons, but also to get around ISP blocks and IP banlists. I don't know how flexible maddy is, but in postfix in case the above scenario wouldn't be resolved, I could have set to use mailgun/mailroute for MS domains only and relay like normally for others.
What do you use as a mail client (on desktop and on phones), and do you have a solution for server side signatures? If so, how well have you found that it supports Reply and Forwarding insertion? Does it support embedding signature logos as hidden attachments to workaround blocked images?
Do you also have any issue with icloud? I somehow get bad IP range and never been able to have them whitelist me, re-attempting seems just put put me into a blackhole queue support on their team :(
i have been using mailinabox on a vps server and all the major email tests say the mailbox is fine.
only gmail treats my emails as spam. others just work fine. i don't know what to do other than having to call receipients and ask them to unspam the mail. That doesnt seem to "train" their spam filters so don't know
I filled the form, was requested documentation from my ISP on the IP address.
I asked my VPS hosting company (since they provide the public IP and therefore act as ISP) and they proactively reached out to Microsoft, who lifted the restriction after that.
So since then no delivery issues. YMMV.
If you intend to host this from your residential address, it can be a good idea to tunnel external traffic over VPN through a VPS or similar. Not only for privacy reasons, but also to get around ISP blocks and IP banlists. I don't know how flexible maddy is, but in postfix in case the above scenario wouldn't be resolved, I could have set to use mailgun/mailroute for MS domains only and relay like normally for others.