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> Email newsletter tools: Old or new, your pick Am I wrong to think that most businesses/people pay for Mailchimp because getting your e-mail actually delivere

> Email newsletter tools: Old or new, your pick Am I wrong to think that most businesses/people pay for Mailchimp because getting your e-mail actually delivered into the inboxes of your target audience/customers is non-trivial? aka, you're going to end up in "spam" otherwise? I find it hard to believe that you can "free-ly" send e-mail to, say, 100,000 e-mails and actually have it get delivered at a high rate? I would love to learn if I'm wrong though. This article could've talked about DataDog vs Jaeger/ELK stack I think for tracing/logs.

dijit 4y ago
> I find it hard to believe that you can "free-ly" send e-mail to, say, 100,000 e-mails and actually have it get delivered at a high rate? I would love to learn if I'm wrong though. You can do this, I have done this, but honestly it's annoyingly painful and you're always one bad ad campaign away from being nuked to death by people marking your emails as spam. There's a lot of rules to follow and even when you follow them you need to ensure that you start emailing a low volume for each new sending IP until the reputation grows over time.
- Breza 4y ago
  This is the correct answer. I work at a company that sends millions of emails every week from our self-hosted IP range. If you have a high quality list of recipients who actually want to hear from you and warm up your IPs gradually, you can be successful.
- Nextgrid 4y ago
  To be fair, if people are marking your emails as spam frequently enough to get your IPs/domains blacklisted then it suggests the system is working as designed and you shouldn’t be sending whatever you’re sending to those people.
  - dijit 4y ago
    Nah, about 2% of my "Thank you for ordering, here is your receipt" mails also get marked as spam. Some number of people just smack the "spam" button for nearly everything that is automated, and those "spam" buttons seem to work on absolute numbers not percentages; so if you have a high number of people in the pool then you will be false flagged eventually. We had a very explicit double opt-in system, made it super easy to unsubscribe, emailed once a month at most; and we had people still marking our communications as spam. I'm not sure what else we could have done to weed out the people who just smack the spam button honestly. That said, there was a lot of variance, emoji in the headline was the campaign that caused 9% of people to mark spam and 20% to unsubscribe, but it was enough to have us blackholed for 2.5 months. I think a major issue is that people don't want to even check how to unsubscribe and they see the “mark as spam” button as a “just make this go away” button.
    - supertrope 4y ago
      I assume you have transactional and marketing emails coming from separate email addresses. If the email ecosystem made it easier for bulk senders, this would just shift the burden onto recipients. Right now the common enemy of illegal spammers externalize the costs of their business onto email providers and users. For every dollar they take they impose 100x that in spam filtering costs. >99.9% of raw email traffic is spam. Blame spammers who offer fake unsubscribe links. Or companies who violate CAN-SPAM by requiring login to unsubscribe instead of one click opt-out. Marking as spam always works.
    - rationalist 4y ago
      How do you prevent people from entering in the wrong address, and thus a random person receiving your emails? If it's just a one-off receipt, I'll delete it. If that business I never had any business with starts spamming me, then I mark it as spam. Second receipt, pisses me off, a third receipt from the same company gets marked as spam etc. If you want to send more than one email, ask for permission. Unfortunately I have a few technology-challenged acquaintances still using my common-ish firslast@ gmail, but once I get them switched over, everything that inbox receives will automatically be marked as spam.
  - monsieurbanana 4y ago
    Could be, or it could be that those systems are so aggressively tuned that newcomers have no chance to not be labeled spam while established players are whitelisted. (I truly don't know, but I don't think it's as simple as you're saying)
    - nottathrowaway3 4y ago
      Email delivery is not purely a protection racket. People use Gmail because they legitimately want to filter out the unsolicited spam, marketing, etc. To an anonymous attacker, there is no cost to send these emails. Middlemen like MailChimp and Sendgrid play the role of converting email from a free, publicly exploitable channel into a paid, KYC one. Email fbfw is the de facto standard communication channel for almost everything, but by design a single computer can send an unlimited number of emails to other addresses. This maybe was a good enough design originally, but now the role of email has grown so much that, today, it should be a paid KYC channel. What is the alternative to spam filtering? Everyone maintains their own allowlist of good senders?
      - me-vs-cat 4y ago
        > What is the alternative to spam filtering? Make sending email cost the sender. No, I don't know how. The best ideas I've heard (1) make the sender store the message and (2) have no hope of being widely adopted.
  - safety1st 4y ago
    Is that the "Just So" story that people who don't work with email at scale believe? Email deliverability is a full time job. There are so many "potential spam" markers that are interpreted differently (and opaquely) by different ESPs. Getting your email delivered to a lot of people is essentially non deterministic. Including a link to a Google Doc in your message body is enough to get you blacklisted by some email providers if you don't have a prior history with them. Yes, there will usually be some process to get off the blacklists and doing it will mostly stick even if you continue to email Google Docs to people. But the key word there is mostly. As I said, deliverability (at least at scale) is a full time job.
  - gscott 4y ago
    It's been my experience that people can't tell the difference between the delete button and the spam button.
  - IncRnd 4y ago
    Except, that's not a fair take. It only takes a moment for a single person to get your ip or domain balacklisted, not a concerted campaign. There are many blacklists that accept direct submissions from any unauthenticated person for any target domain/ip. What's difficult is not to get onto a blacklist but to get off of a blacklist.
  - mrmattyboy 4y ago
    One thing to say to this.. I work at a company and have personally setup quite a few mail servers for mass email sending and warming up IPs.. not fun.. (these are all legitimate interest emails) I was in a meeting with a couple of people from the team and a QA engineer mentioned that everytime he's done with an email in gmail, he spams it off... _wut_.. Whilst yes, we have been blacklisted a handful of times and, based on spam reports (feedback loops), people do mark emails as spam for completely nonsensical reasons... e.g. users signing up, (getting and using the activation email), using the service and then spamming the activation email. Edit: I definitely think there's a bell curve for sending your own emails: * If you have a very small platform (at least in my experience), reputation doesn't mean that much, emails are generally accepted by providers (assuming IPs that you used haven't been previously used for spammy activity), so self-hosting might make some sense (though a third-party probably wouldn't be too expensive if you did want to). * If you start sending 100s-1000s of emails/day, I guess some third party solution would make sense, since running dedicated IPs/domains and servers just for sending emails might not be beneficial. * As you go to sending 100K+ emails a day, personally, I think setting up servers starts making more sense
  - samstave 4y ago
    See my other comment below on how IP blocks for IPv4 went through the roof on price and availabilty... The global spam market is what caused the hockey-stick rise in IPv4 "shortage"
- capableweb 4y ago
  + unsurprisingly, lots of hosting providers disable SMTP/block port 25/ban you if any email sending is being detected coming from your instances, legitimate or not, as the problem with hosting IPs that are sending spam is so annoying (and even illegal in some places).
- deleted 4y ago
  [deleted]
- djbusby 4y ago
  How does one even know that message are being tagged as spam?
  - dijit 4y ago
    Depending on the provider you can receive a “bounce” response. Yahoo and Hotmail do this, Google was a little more opaque if memory serves.
  - aendruk 4y ago
    https://en.wikipedia.org/wiki/Feedback_loop_(email) https://en.wikipedia.org/wiki/Feedback_loop_(email)
- Thaxll 4y ago
  You can't just send 100k emails with a good delivery rate, if you're a nobody Gmail will never trust you. You can follow all the rules the want ( dkim, spf etc .. ) somehow it will no be delivered because you don't know exaclty how they rate your IP.
galdor 4y ago
You go with Mailchimp (or equivalent) for newsletters because they give you the subscription form, handle email verification, unsubscriptions, GDPR mentions everywhere, provide useful stats and notifications, segmentation and targeting… Getting email delivered is indeed really hard, especially if you send thousands of emails, but building all these other features is insanely time consuming. The cost of Mailchimp is negligible in comparison. Same reason why companies use Sendgrid for marketing campaigns.
- SoftTalker 4y ago
  Anything I get from Mailchimp or similar services is auto-flagged as spam by rule.
gwbrooks 4y ago
You can get high deliverability -- the keys, whether you're using your own servers or someone else's come down to a clean list that won't generate complaints and staying within the TOS of your mailserver host or third-party SMTP service. Host your mail-creation/list-management/analytics stack yourself (I like Mautic and MailWizz but there are other options) and use a third party for SMTP services. Amazon SES charges $1 per 10,000 emails; other services are slightly more expensive but it's all still very affordable.
- tedivm 4y ago
  I'm not sure why you're getting the downvotes but this is the way for people who want some level of self hosting. I finally gave up hosting my own mail server about two years ago- I had been self hosting email since 2005, but it reached the point where delivery to the big companies was extremely difficult. If someone wants to host their own software but actually have their emails delivered they really do need a third party SMTP service that specialized in deliverability or has a big company behind it.
  - nottathrowaway3 4y ago
    You're sending your emails over the internet anyway. You're paying for the reputation of the 3p smtp service and it's a pretty liquid/perfect market.
  - wankle 4y ago
    > I finally gave up hosting my own mail server A lot of us haven't. > If someone wants to host their own software but actually have their emails delivered they really do need a third party SMTP service that specialized in deliverability or has a big company behind it. A lot of us don't.
- locustous 4y ago
  I've had really poor deliverability from SES. Our emails went straight to spam on many providers. Just trying to do email verification on new signups.
luckylion 4y ago
That's also why the phishing campaigns now use Amazon SES (and amazon happily lets them, as long as they pay, it seems): their email will get delivered.
samstave 4y ago
The biggest aspect that used to be used in spam detection (from an OSI, not a content reading perspective) was source IP blocks. Many people dont realize that spam was the original source for social networking... I cant type up all the history I know quickly, but Friendster (who 'invented the social graph', HI5, Tagged, MySpace, were all started as an overlay to email harvesting mechanisms to --> spam.... They needed to create high value email-lists of valid emails. Asking for such, was stupid as most people rejected it. Then, they figured out that adding a service (chat and share with your friends, give us your email and their email so we can connect you by sending them invites etc) was the best social-engineering (the 'hacker' meaning) mechanism was to have people validate their personal email, offer a novel e-'service' to 'connect' with your friends within some context - and have you pre-validate the email list based on your invites and contacts... then parlay MLM structure to create better more validated email lists. Then you sell the lists on the BM to spammers looking to avoid a high bounce rate based on real emails. Then they started nefariously stealing your contacts with auto-opt-in agreements and such.... Then as the battle btwn spam and socially-interesting services ramped up the spam companies (such as Postini (which was bought by google) became the spam filters (selling their services to BigCorps) began to realize that filtering on the sending IPs was a good measure for determining spam (along with rate-limiting, and other aspects) - such that spammers were getting blocked based on delivery IP blocks. This set-off a market incentive for spammers to buy up swaths of IPv4 blocks so they could swap out IPs... Then there were many ranges, sources, tracrts etc used to determine senders and ID them as spammers etc.... So - the spammers invented VPN/Tunneling delivery routes such they could send to a number of various global relays so that they could send from a central source of machines, but be delivered to the endpoints from a variety of global IP blocks. There was a market for IPv4 blocks all over the world and spammers were spending big bucks on all aspects, from paying for the IP blocks, relationships with ISP/VPN/etc tech.... All while attempting to provide what was a thin layer of utility service to the user to keep what was effectively continued access to the growing address books of their users and keep them engaged on the platform such that they could keep knowing if existing or new contacts were valid. There were even back-room deals between spammers/tech/isp etc to allow access. So, the "social networks" we know know of were birthed literally upon spam. - Have you ever wondered why as soon as tiktock came out, all of a sudden a fuck-ton of spam was hitting your gmail inbox (previously postini) <-- Because tictock was eating the revenue lunch. Zuck literally stated that the entire revenue model for FB was "senator, we sell ads" When in an interview with Google, they asked "what kind of company do you think google is "Well, most people think youre a search engine, but youre actually an advertisement correlation engine" In an interview with Twitter (dont forget about the infamous ATT room 641A?) - what do you think twitter is: "Twitter is a global sentiment monitering engine" (this was ~2006?8? I cant recall) -- Source: I know these founders and many of the original devops members from the above companies, and other more scary outcomes from the above statements. And here we are today with the advanced learning all built upon "consumption" ad algos
j45 4y ago
A dedicated IP address can be warmed up to deliver email well enough but it can take some time. A mail server software like mdaemon can quickly handle the heavy lifting of improving deliverability. It’s a small price for the deliverability. I’m just a former user of it. It’s ok to use an external email provider for outgoing email delivery. ESPs (email service providers) are handy because they can separate outgoing transactional emails from marketing ones to ensure deliverability.
jd3 4y ago
> I find it hard to believe that you can "free-ly" send e-mail to, say, 100,000 e-mails and actually have it get delivered at a high rate? I would love to learn if I'm wrong though. The company I work for has an outbox feature which supports this and it was a non-trivial problem to solve. We ended up using sparkpost with a bunch of modifications to isolate potentially bad actors (i.e., clients who pay for our software but send what is basically spam) to an individual sending pool. We also have CSMs that handle this and help to coach clients to not send spam. https://support.sparkpost.com/docs/deliverability https://support.sparkpost.com/docs/deliverability

dijit 4y ago

> I find it hard to believe that you can "free-ly" send e-mail to, say, 100,000 e-mails and actually have it get delivered at a high rate? I would love to learn if I'm wrong though. You can do this, I have done this, but honestly it's annoyingly painful and you're always one bad ad campaign away from being nuked to death by people marking your emails as spam. There's a lot of rules to follow and even when you follow them you need to ensure that you start emailing a low volume for each new sending IP until the reputation grows over time.

Breza 4y ago
This is the correct answer. I work at a company that sends millions of emails every week from our self-hosted IP range. If you have a high quality list of recipients who actually want to hear from you and warm up your IPs gradually, you can be successful.
Nextgrid 4y ago
To be fair, if people are marking your emails as spam frequently enough to get your IPs/domains blacklisted then it suggests the system is working as designed and you shouldn’t be sending whatever you’re sending to those people.
- dijit 4y ago
  Nah, about 2% of my "Thank you for ordering, here is your receipt" mails also get marked as spam. Some number of people just smack the "spam" button for nearly everything that is automated, and those "spam" buttons seem to work on absolute numbers not percentages; so if you have a high number of people in the pool then you will be false flagged eventually. We had a very explicit double opt-in system, made it super easy to unsubscribe, emailed once a month at most; and we had people still marking our communications as spam. I'm not sure what else we could have done to weed out the people who just smack the spam button honestly. That said, there was a lot of variance, emoji in the headline was the campaign that caused 9% of people to mark spam and 20% to unsubscribe, but it was enough to have us blackholed for 2.5 months. I think a major issue is that people don't want to even check how to unsubscribe and they see the “mark as spam” button as a “just make this go away” button.
  - supertrope 4y ago
    I assume you have transactional and marketing emails coming from separate email addresses. If the email ecosystem made it easier for bulk senders, this would just shift the burden onto recipients. Right now the common enemy of illegal spammers externalize the costs of their business onto email providers and users. For every dollar they take they impose 100x that in spam filtering costs. >99.9% of raw email traffic is spam. Blame spammers who offer fake unsubscribe links. Or companies who violate CAN-SPAM by requiring login to unsubscribe instead of one click opt-out. Marking as spam always works.
  - rationalist 4y ago
    How do you prevent people from entering in the wrong address, and thus a random person receiving your emails? If it's just a one-off receipt, I'll delete it. If that business I never had any business with starts spamming me, then I mark it as spam. Second receipt, pisses me off, a third receipt from the same company gets marked as spam etc. If you want to send more than one email, ask for permission. Unfortunately I have a few technology-challenged acquaintances still using my common-ish firslast@ gmail, but once I get them switched over, everything that inbox receives will automatically be marked as spam.
- monsieurbanana 4y ago
  Could be, or it could be that those systems are so aggressively tuned that newcomers have no chance to not be labeled spam while established players are whitelisted. (I truly don't know, but I don't think it's as simple as you're saying)
  - nottathrowaway3 4y ago
    Email delivery is not purely a protection racket. People use Gmail because they legitimately want to filter out the unsolicited spam, marketing, etc. To an anonymous attacker, there is no cost to send these emails. Middlemen like MailChimp and Sendgrid play the role of converting email from a free, publicly exploitable channel into a paid, KYC one. Email fbfw is the de facto standard communication channel for almost everything, but by design a single computer can send an unlimited number of emails to other addresses. This maybe was a good enough design originally, but now the role of email has grown so much that, today, it should be a paid KYC channel. What is the alternative to spam filtering? Everyone maintains their own allowlist of good senders?
    - me-vs-cat 4y ago
      > What is the alternative to spam filtering? Make sending email cost the sender. No, I don't know how. The best ideas I've heard (1) make the sender store the message and (2) have no hope of being widely adopted.
- safety1st 4y ago
  Is that the "Just So" story that people who don't work with email at scale believe? Email deliverability is a full time job. There are so many "potential spam" markers that are interpreted differently (and opaquely) by different ESPs. Getting your email delivered to a lot of people is essentially non deterministic. Including a link to a Google Doc in your message body is enough to get you blacklisted by some email providers if you don't have a prior history with them. Yes, there will usually be some process to get off the blacklists and doing it will mostly stick even if you continue to email Google Docs to people. But the key word there is mostly. As I said, deliverability (at least at scale) is a full time job.
- gscott 4y ago
  It's been my experience that people can't tell the difference between the delete button and the spam button.
- IncRnd 4y ago
  Except, that's not a fair take. It only takes a moment for a single person to get your ip or domain balacklisted, not a concerted campaign. There are many blacklists that accept direct submissions from any unauthenticated person for any target domain/ip. What's difficult is not to get onto a blacklist but to get off of a blacklist.
- mrmattyboy 4y ago
  One thing to say to this.. I work at a company and have personally setup quite a few mail servers for mass email sending and warming up IPs.. not fun.. (these are all legitimate interest emails) I was in a meeting with a couple of people from the team and a QA engineer mentioned that everytime he's done with an email in gmail, he spams it off... _wut_.. Whilst yes, we have been blacklisted a handful of times and, based on spam reports (feedback loops), people do mark emails as spam for completely nonsensical reasons... e.g. users signing up, (getting and using the activation email), using the service and then spamming the activation email. Edit: I definitely think there's a bell curve for sending your own emails: * If you have a very small platform (at least in my experience), reputation doesn't mean that much, emails are generally accepted by providers (assuming IPs that you used haven't been previously used for spammy activity), so self-hosting might make some sense (though a third-party probably wouldn't be too expensive if you did want to). * If you start sending 100s-1000s of emails/day, I guess some third party solution would make sense, since running dedicated IPs/domains and servers just for sending emails might not be beneficial. * As you go to sending 100K+ emails a day, personally, I think setting up servers starts making more sense
- samstave 4y ago
  See my other comment below on how IP blocks for IPv4 went through the roof on price and availabilty... The global spam market is what caused the hockey-stick rise in IPv4 "shortage"
capableweb 4y ago
+ unsurprisingly, lots of hosting providers disable SMTP/block port 25/ban you if any email sending is being detected coming from your instances, legitimate or not, as the problem with hosting IPs that are sending spam is so annoying (and even illegal in some places).
deleted 4y ago
[deleted]
djbusby 4y ago
How does one even know that message are being tagged as spam?
- dijit 4y ago
  Depending on the provider you can receive a “bounce” response. Yahoo and Hotmail do this, Google was a little more opaque if memory serves.
- aendruk 4y ago
  https://en.wikipedia.org/wiki/Feedback_loop_(email) https://en.wikipedia.org/wiki/Feedback_loop_(email)
Thaxll 4y ago
You can't just send 100k emails with a good delivery rate, if you're a nobody Gmail will never trust you. You can follow all the rules the want ( dkim, spf etc .. ) somehow it will no be delivered because you don't know exaclty how they rate your IP.

galdor 4y ago

You go with Mailchimp (or equivalent) for newsletters because they give you the subscription form, handle email verification, unsubscriptions, GDPR mentions everywhere, provide useful stats and notifications, segmentation and targeting… Getting email delivered is indeed really hard, especially if you send thousands of emails, but building all these other features is insanely time consuming. The cost of Mailchimp is negligible in comparison. Same reason why companies use Sendgrid for marketing campaigns.

SoftTalker 4y ago
Anything I get from Mailchimp or similar services is auto-flagged as spam by rule.

gwbrooks 4y ago

You can get high deliverability -- the keys, whether you're using your own servers or someone else's come down to a clean list that won't generate complaints and staying within the TOS of your mailserver host or third-party SMTP service. Host your mail-creation/list-management/analytics stack yourself (I like Mautic and MailWizz but there are other options) and use a third party for SMTP services. Amazon SES charges $1 per 10,000 emails; other services are slightly more expensive but it's all still very affordable.

tedivm 4y ago
I'm not sure why you're getting the downvotes but this is the way for people who want some level of self hosting. I finally gave up hosting my own mail server about two years ago- I had been self hosting email since 2005, but it reached the point where delivery to the big companies was extremely difficult. If someone wants to host their own software but actually have their emails delivered they really do need a third party SMTP service that specialized in deliverability or has a big company behind it.
- nottathrowaway3 4y ago
  You're sending your emails over the internet anyway. You're paying for the reputation of the 3p smtp service and it's a pretty liquid/perfect market.
- wankle 4y ago
  > I finally gave up hosting my own mail server A lot of us haven't. > If someone wants to host their own software but actually have their emails delivered they really do need a third party SMTP service that specialized in deliverability or has a big company behind it. A lot of us don't.
locustous 4y ago
I've had really poor deliverability from SES. Our emails went straight to spam on many providers. Just trying to do email verification on new signups.

luckylion 4y ago

That's also why the phishing campaigns now use Amazon SES (and amazon happily lets them, as long as they pay, it seems): their email will get delivered.

samstave 4y ago

The biggest aspect that used to be used in spam detection (from an OSI, not a content reading perspective) was source IP blocks. Many people dont realize that spam was the original source for social networking... I cant type up all the history I know quickly, but Friendster (who 'invented the social graph', HI5, Tagged, MySpace, were all started as an overlay to email harvesting mechanisms to --> spam.... They needed to create high value email-lists of valid emails. Asking for such, was stupid as most people rejected it. Then, they figured out that adding a service (chat and share with your friends, give us your email and their email so we can connect you by sending them invites etc) was the best social-engineering (the 'hacker' meaning) mechanism was to have people validate their personal email, offer a novel e-'service' to 'connect' with your friends within some context - and have you pre-validate the email list based on your invites and contacts... then parlay MLM structure to create better more validated email lists. Then you sell the lists on the BM to spammers looking to avoid a high bounce rate based on real emails. Then they started nefariously stealing your contacts with auto-opt-in agreements and such.... Then as the battle btwn spam and socially-interesting services ramped up the spam companies (such as Postini (which was bought by google) became the spam filters (selling their services to BigCorps) began to realize that filtering on the sending IPs was a good measure for determining spam (along with rate-limiting, and other aspects) - such that spammers were getting blocked based on delivery IP blocks. This set-off a market incentive for spammers to buy up swaths of IPv4 blocks so they could swap out IPs... Then there were many ranges, sources, tracrts etc used to determine senders and ID them as spammers etc.... So - the spammers invented VPN/Tunneling delivery routes such they could send to a number of various global relays so that they could send from a central source of machines, but be delivered to the endpoints from a variety of global IP blocks. There was a market for IPv4 blocks all over the world and spammers were spending big bucks on all aspects, from paying for the IP blocks, relationships with ISP/VPN/etc tech.... All while attempting to provide what was a thin layer of utility service to the user to keep what was effectively continued access to the growing address books of their users and keep them engaged on the platform such that they could keep knowing if existing or new contacts were valid. There were even back-room deals between spammers/tech/isp etc to allow access. So, the "social networks" we know know of were birthed literally upon spam. - Have you ever wondered why as soon as tiktock came out, all of a sudden a fuck-ton of spam was hitting your gmail inbox (previously postini) <-- Because tictock was eating the revenue lunch. Zuck literally stated that the entire revenue model for FB was "senator, we sell ads" When in an interview with Google, they asked "what kind of company do you think google is "Well, most people think youre a search engine, but youre actually an advertisement correlation engine" In an interview with Twitter (dont forget about the infamous ATT room 641A?) - what do you think twitter is: "Twitter is a global sentiment monitering engine" (this was ~2006?8? I cant recall) -- Source: I know these founders and many of the original devops members from the above companies, and other more scary outcomes from the above statements. And here we are today with the advanced learning all built upon "consumption" ad algos

j45 4y ago

A dedicated IP address can be warmed up to deliver email well enough but it can take some time. A mail server software like mdaemon can quickly handle the heavy lifting of improving deliverability. It’s a small price for the deliverability. I’m just a former user of it. It’s ok to use an external email provider for outgoing email delivery. ESPs (email service providers) are handy because they can separate outgoing transactional emails from marketing ones to ensure deliverability.

jd3 4y ago

> I find it hard to believe that you can "free-ly" send e-mail to, say, 100,000 e-mails and actually have it get delivered at a high rate? I would love to learn if I'm wrong though. The company I work for has an outbox feature which supports this and it was a non-trivial problem to solve. We ended up using sparkpost with a bunch of modifications to isolate potentially bad actors (i.e., clients who pay for our software but send what is basically spam) to an individual sending pool. We also have CSMs that handle this and help to coach clients to not send spam. https://support.sparkpost.com/docs/deliverability https://support.sparkpost.com/docs/deliverability