What tools do you use to monitor IP cleanliness? I monitor mine with free blacklist monitoring tools, but a lot of my emails to corporate addresses end up bouncing. The rejection message often gives a generic error so I'm not sure if that's my fault or not.

I use the free tools as well, but most of the folks I consult for, I also administer their mail account server @ Google or Microsoft, so I can keep an eye on both sides of the transaction. Implementing SPF/DKIM/DMARC/smtp-tls also helped keep things clean. You can register as a postmaster @ AOL, Microsoft & Google, and also get reports if something is reported as spam.

A well behaved remote mail server should either reject/bounce the message, or deliver it to a user's spam folder, it should never just drop it. Unfortunately, It's near impossible to determine if your message ended up in a user's spam folder :(

My server sends 50-100 messages a month, tops, and I never send mass messages, just direct messages to family, friends & customers. The biggest issue I had was when Rackspace periodically (+ voluntarily) reported their VPS IP space to Spamhaus, which required me to inform Spamhaus that I was responsible for that specific IP, and it should not be on the blacklist.

"I use the free tools as well, but most of the folks I consult for, I also administer their mail account server @ Google or Microsoft, so I can keep an eye on both sides of the transaction."

Is this new ? I have been part of discussions on HN about personal mail servers for ... 8 years ? This is the first I have heard someone mention registering their mail server with google ...

Search for "Google Postmaster tools" or check out

https://postmaster.google.com/managedomains

You don't have to register per-se, but you get access to reports for your domain so you can see any potential trouble.

Corporate email admins can be more aggressive and unpredictable than big ISPs or Google or Microsoft, because they have a more direct relationship with their fellow staff. They can train users how to manage their own whitelists, and they usually already have an IT helpdesk staffed answer questions and concerns from users.

Corporate email admins can also be opinionated about email senders because their email system is only for their employees' work, specifically. They are less likely than Gmail to care about email from the little guys who are trying to build an audience or business. They definitely don't see it as their job to provide startups and random people with access to the inboxes of their staff. They will err on the side of saying no to unfamiliar email.

Corporate email is where it gets hard. You can have a clean IP, all the authentication options configured correctly, and still struggle to get out of the spam folder. This is one reason businesses will pay for big-name email platforms, which have spent a lot of time and money building good reputations with corporate teams, and have people who specialize in maintaining those reputations.

I've noticed that a lot of corporations set up greylisting [1] for their mail servers. So that might be one reason why you are seeing a lot of bounces, and you just need to resend the email after a few minutes. I use SendGrid, which automatically handles this. But it's always annoying to get these bounce notifications.

[1] https://en.wikipedia.org/wiki/Greylisting

A useful tool is sender score: https://www.senderscore.org/lookup.php?lookup=0

Oh, good, I have an MX record. Glad somebody could confirm that for me.

The domain lookup info is silly, but if you lookup your smtp server IP it’ll show you a score that in my experience is correlated to the probability of it not being in a blacklist.

You can use rblmon.com to monitor IPs for inclusion in public blacklists. There are other SaaS alternatives in this space as well, in addition to self-hosted scripts/applications. Amazingly, RBLs are still a thing that people need to care about, after so many years.

Disclaimer: I'm one of the developers behind RBLMon.

You could utilize a managed SMTP service like AWS SES or Mailgun, which is free for up to 10,000 emails per month. They have reference configurations for various MTAs[1] and you wouldn't have to manage IP reputation yourself.

[1] https://documentation.mailgun.com/en/latest/user_manual.html...

Whenever a business justifies its pricing by pointing to costs it’s either in deep trouble or run by amateurs. Big red flag IMO.

Anyone voting this down, ask yourself: why do I, as customer, care about your costs. That’s YOUR business, not mine. You tell me about your costs, my mind turns off and I don’t want to hear anything else you say.

So, what, you'd rather hear some bullshit PR excuse about maximizing customer value or whatever?

Also, as a customer I do not mind thinking about a business' costs. In fact I want to know that a business is pricing a reasonable margin above costs and no more. I have way more respect for companies that don't see the need to mindlessly pad their profits. Not everyone is you.

(Not saying RS is being honest here but it is important to push back against this "pay no attention to what's going on behind the curtains" thinking)

I love thinking about businesses and their costs, but not as the consumer. As the consumer I care only about the price to me. If the business exposes me to their business, I no longer benefit as much from their business. And yes, would rather hear some PR BS, to be honest, than some sob story about how they aren’t good at business (which is all I hear when they start telling me about how this cost went up or that cost went up).

Hah! I'm in a similar position. I have a really old machine at Rackspace ($20/mo) from about 2010 that's running websites for some family and friends. I could easily transition to a ~$5/mo VPS elsewhere but I really don't want to deal with the migration hurdles.

It's been a while since I've had to manage anything hosted with Rackspace but:

They just announced a $5 hike in price this month for "fanatical" support, I haven't opened a support request with them in eons:

How is their fanatical support lately? I recall my company (at the time) paying through the nose for a pretty responsive Fanatical Support SLA, such that I could call in at 2AM and almost every time get someone in no more than three rings-central time zone, no less-for our dedicated services account.

Curious how it is for other customers who might not have had a tech budget the size of ours and could swing heavy hammers to get such support.

Boy they have to be angry with customers like me. I have Rackspace account created in February of 2014 and it was free back then. I think 2 months later they start charging mandatory $50. Like anyone else I moved all my servers out and only using their DNS console for DNS management which is good enough.

About your mailservers: location doesn't matter, as reputation is being build over the time. I have Digital Ocean $5/1GB machine that was previously used for heavy spamming (had to submit tickets with all biggest SpamHouses) and since then has pristine reputation with constant 97-99 SpamScore, etc. You just need about 45 days of constant raising volume of mailouts and you be fine. This machine currently does about 40,000 mailouts a day.

It's been more like 1.5-2 years I sat on an IP, and had AWS setup the reverse record for it. I parked it on my SPF record, then started slowly sending messages through it after 6 months. I was not in a hurry, and I figured the extra time woulden't hurt.

DO's equivalent Elastic IP product can't be used to originate email, unfortunately. They actively block it, and it's against their ToS (Last time I looked). Otherwise I would have preferred to host it there. If you allocate a Droplet, groom it's IP, and then terminate it (either for yours or their reasons), they only "promise" to give you back the same IP, and I'd hate to have to setup a new IP in a rush.

That's not my experience.

Before I setup my DO I asked them can I set up ESP? They said absolutely. AFAIK they only ban constant abusers. I sent to very clean and engaged list (noone above 45 days of inactivity) and hadn't had any problems. I have "emergency setup" on different hosting but you are right on point it would take month to come back to same mailing levels.

DO TOS doesn't say you can't send emails. Their control panel allows you to setup rDNS yourself BTW.

These days largest ESPs (Google, Yahoo/Rocketmail, AOL/Live/Outlook/Hotmail, GMX, Wanddo, Orange, UOl, BOL) only really look at IP in 4 categories: narrow whitelist (other biggest mailers, private contracts [banks mostly]), wide whitelist (static IPs of all sort including your $5 DO), greylist (home IPs, mobile IPs, all other IPs that probably should be mailout out in the first place), blacklist (in terms of you land there forever - don't confuse with having your IP blacklisted). Long gone times when ESPs tried to figure on some scale 1-100 how good your IP is.

What are you using for running mail server?

I've been using mailinabox and am generally happy with it as is mostly a hobby server, but am curious what others are running.