> I remember many people running their own SMTP server used to have massive issues with their outgoing mail being silently or non-silently ignored or sent to the spam folder. Does this take care of this? "Mostly" really isn't good enough.
Frankly I've had mixed results over several years of hosting my own personal email server, even with a valid PTR, SPF, and DKIM. Most SMB and personal email systems I interact with are fine, as aside from Bayesian filtering those tend to rely heavily on blacklists which I am responsible enough to keep myself off of—easy given that I'm the server's only user. And I've never had an issue sending to Gmail users.
Microsoft is the real f-up in this regard, originally with Hotmail and now with the updated Outlook.com. Even though I'm on no blacklists and pass both their SPF and DKIM checks:
Authentication-Results: hotmail.com; spf=pass (sender IP is XXX.XXX.XXX.XXX) smtp.mailfrom=redacted@example.com; dkim=pass header.d=example.com; x-hmca=pass header.id=redacted@example.com
X-SID-PRA: redacted@example.com
X-AUTH-Result: PASS
X-SID-Result: PASS
my messages still end up in the Junk folder.
If you visit their support page you're recommended to join their partner Return Path's Sender Score Certified Email program to stop junk filtering of your legitimate messages. That's great, if you're a medium-sized organization that doesn't mind paying their certification fee; but Return Path won't even allow an individual to register (I've tried). I'm familiar with Hanlon's razor, "never attribute to malice that which is adequately explained by stupidity", but this at least feels like a racket.
Unfortunately I don't know what else to do, other than continue to advise everyone I know not to use Outlook.com and friends.
And to finally answer your question, if this VM runs its own DNS then it probably takes care of SPF and DKIM adequately, but you'll likely have to contact your hosting provider for the PTR record, which is at least as important. But even following those best practices you can still have delivery issues such as I have described above, leading to the unfortunate reality that if you really need a message to be delivered you're probably better off sending it through Gmail.
I was suffering the same problem about 7 years ago on my own personal mail server. I discovered that if I padded out the message headers with a load of junk headers to push the message size up beyond about 50KB, then the otherwise exact same message would arrive in the Inbox at Hotmail rather than being blackholed.
I will. One thing I can add is Microsoft hates the word PayPal - mention paypay in your email and it gets killed, take out that one word and it goes straight through.
hotmail used to actively blackhole e-mail from smaller servers, no bounce, no warning, nothing. just accept it and throw it away.
i don't know if they still do that, but it was far easier to convince everyone i knew at the time that hotmail was garbage, rather than making any headway with their mail admins.
My only issue in the last 2 years was with Gmail, which I eventually discovered on accident was apparently because of my lack of appropriate ipv6 records in my SPF tag.
I didn't catch it for a while because so much of the email world simply assumes ipv4, but traffic happily exits my ipv6 interface when the destination supports it.
Frankly I've had mixed results over several years of hosting my own personal email server, even with a valid PTR, SPF, and DKIM. Most SMB and personal email systems I interact with are fine, as aside from Bayesian filtering those tend to rely heavily on blacklists which I am responsible enough to keep myself off of—easy given that I'm the server's only user. And I've never had an issue sending to Gmail users.
Microsoft is the real f-up in this regard, originally with Hotmail and now with the updated Outlook.com. Even though I'm on no blacklists and pass both their SPF and DKIM checks:
my messages still end up in the Junk folder.If you visit their support page you're recommended to join their partner Return Path's Sender Score Certified Email program to stop junk filtering of your legitimate messages. That's great, if you're a medium-sized organization that doesn't mind paying their certification fee; but Return Path won't even allow an individual to register (I've tried). I'm familiar with Hanlon's razor, "never attribute to malice that which is adequately explained by stupidity", but this at least feels like a racket.
Unfortunately I don't know what else to do, other than continue to advise everyone I know not to use Outlook.com and friends.
And to finally answer your question, if this VM runs its own DNS then it probably takes care of SPF and DKIM adequately, but you'll likely have to contact your hosting provider for the PTR record, which is at least as important. But even following those best practices you can still have delivery issues such as I have described above, leading to the unfortunate reality that if you really need a message to be delivered you're probably better off sending it through Gmail.