Email deliverability to Microsoft email servers
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I worked at a company before who offered transactional email services for business customers (we‘re talking like 1-2 million mails per day, e.g. banks that send out notifications or password reset links etc.). Believe me, email reputation was a 24/7 job.
I would, therefore, rather rely on a pro for relaying email and keeping reputation.
And I don’t blame it so much on Microsoft/Google but all these little a**holes who sign up a VPS and start sending their shit. You just can’t have nice things anymore…. -
I worked at a company before who offered transactional email services for business customers (we‘re talking like 1-2 million mails per day, e.g. banks that send out notifications or password reset links etc.). Believe me, email reputation was a 24/7 job.
I would, therefore, rather rely on a pro for relaying email and keeping reputation.
And I don’t blame it so much on Microsoft/Google but all these little a**holes who sign up a VPS and start sending their shit. You just can’t have nice things anymore….@necrevistonnezr Yeah, I learned a few things from the research, so it was a bit of commentary on that to see what other experience and successes we might find.
I think I misunderstood how the relaying was implemented, now I know that, and a couple of other things, much happier that there are solutions for all occasions. Hopefully some tips to hep others here, and additions to the documentation should help, too.
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@here I've not used mail relays with a Cloudron email service setup before (only used them for email newsletter sending).
Anyone know if the sent mail is still stored on the IMAP server before it's sent to the relay to deliver?
@marcusquinn said in Email deliverability to Microsoft email servers:
Anyone know if the sent mail is still stored on the IMAP server before it's sent to the relay to deliver?
This depends on your email client settings actually. Basically, most email clients save a copy of the email you are sending in the 'Sent' folder, but they can be configured not to. The saved copy is uploaded to your actual 'mailbox' via IMAP - but this is not equivalent to sending an email, this is just saving a copy that doesn't leave your mailbox. IMAP is basically what allows you to organize and upload and download to that mailbox - and it doesn't have anything to do with actually sending of the email.
Actual outgoing email goes through a different protocol called SMTP - and it doesn't touch your actual 'mailbox' at all except for when email is delivered to you. SMTP is used by your email client to send your email to your own email server, and then SMTP is used again from your server to the receiver's email server (and sometimes multiple chains if it's configured that way). So it's basically just a protocol for sending email.
Anyways, best of luck with all of this
. Sorry it's being so painful to get it working. -
@marcusquinn said in Email deliverability to Microsoft email servers:
Anyone know if the sent mail is still stored on the IMAP server before it's sent to the relay to deliver?
This depends on your email client settings actually. Basically, most email clients save a copy of the email you are sending in the 'Sent' folder, but they can be configured not to. The saved copy is uploaded to your actual 'mailbox' via IMAP - but this is not equivalent to sending an email, this is just saving a copy that doesn't leave your mailbox. IMAP is basically what allows you to organize and upload and download to that mailbox - and it doesn't have anything to do with actually sending of the email.
Actual outgoing email goes through a different protocol called SMTP - and it doesn't touch your actual 'mailbox' at all except for when email is delivered to you. SMTP is used by your email client to send your email to your own email server, and then SMTP is used again from your server to the receiver's email server (and sometimes multiple chains if it's configured that way). So it's basically just a protocol for sending email.
Anyways, best of luck with all of this
. Sorry it's being so painful to get it working.@michaelpope Yeah, one of those things I should have known, but have used relays in every other context but this over the years, so just was leaning on the experience here for a sanity check
Now I'm sure, it actually makes far more sense to just use for all servers. I'd also fallen into the thinking that my dedicated IPs were better for controlling deliverability, but had never thought that lower volumes might be a negative factor.
I'm good with pain, it's just the price of filling knowledge gaps, and it it's not obvious or common knowledge, it's probably more valuable experience, too.
Think I have a happy solution now, either using Elastic Mail for pure relaying, or Namecheap or any other mass-market provider SMTP relay for outbound.
Still not ideal for 100% privacy, but you'd hope most are good to their word of not storing data beyond retention periods for logs, and the inbound for things like 2FA can still remain as private as the Cloudron instance can be kept.
Maybe there's an add-on service idea for Cloudron in also offering its own relay.
Ultimately, with non-E2EE, you have to trust some man in the middle, andI feel we have a good measure of trust ethics here.
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FWIW, I have found the best email delivery using Postmark, a REASONABLE, paid service provider. We have used Mailgun (shared IP) and periodically needed to switch IP addresses once the IP address got "poisoned" by someone else. Dedicated IP works, but is very expensive. If you do not send a large volume of emails, it may be difficult to earn a good reputation.
For all those reasons, we have moved most of our outbound email to Postmark. Deliverability is excellent. You can (and should) establish individual "servers" for different domains/email streams (marketing vs. transactional).
We get confirmation that emails were delivered to the recipient's mail server. That's how we found out that some of our emails were being "blackholed" by a large inbox provider (guess who?)For an expenditure of $US20/month we can send 10K/month and have delivery records for 90 days. Totally worth it.
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FWIW, I have found the best email delivery using Postmark, a REASONABLE, paid service provider. We have used Mailgun (shared IP) and periodically needed to switch IP addresses once the IP address got "poisoned" by someone else. Dedicated IP works, but is very expensive. If you do not send a large volume of emails, it may be difficult to earn a good reputation.
For all those reasons, we have moved most of our outbound email to Postmark. Deliverability is excellent. You can (and should) establish individual "servers" for different domains/email streams (marketing vs. transactional).
We get confirmation that emails were delivered to the recipient's mail server. That's how we found out that some of our emails were being "blackholed" by a large inbox provider (guess who?)For an expenditure of $US20/month we can send 10K/month and have delivery records for 90 days. Totally worth it.
@crazybrad said in Email deliverability to Microsoft email servers:
send 10K/month
Yeah, if I need to send large volumes of mail I'd certainly give Postmark a try given how many people here seem to be recommending it.
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@crazybrad said in Email deliverability to Microsoft email servers:
send 10K/month
Yeah, if I need to send large volumes of mail I'd certainly give Postmark a try given how many people here seem to be recommending it.
@jdaviescoates I send nowhere near that limit. I use it for business and personal email accounts because of the deliverability issue. The monthly cost is trivial compared to the time wasted trying to troubleshoot issues.
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Deliverability to Microsoft and Google are a real challenge, that's for sure. Full DMARC with discard/delete options does help.
If we could just override the default Cloudron email configuration on a per app basis, it would be much easier to deal with
We're happy using our Cloudron Digital Ocean hosted droplet foliovision.net SMTP to deliver internal emails but can't use it for client emails (not reliable enough). Unfortunately Cloudron is missing a per application option not to hijack the app's email settings. This oversight caused us serious issues with InvoiceNinja where we had endless trouble with invoice deliverability due to the SMTP settings being silently erased on every restart.
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Deliverability to Microsoft and Google are a real challenge, that's for sure. Full DMARC with discard/delete options does help.
If we could just override the default Cloudron email configuration on a per app basis, it would be much easier to deal with
We're happy using our Cloudron Digital Ocean hosted droplet foliovision.net SMTP to deliver internal emails but can't use it for client emails (not reliable enough). Unfortunately Cloudron is missing a per application option not to hijack the app's email settings. This oversight caused us serious issues with InvoiceNinja where we had endless trouble with invoice deliverability due to the SMTP settings being silently erased on every restart.
@foliovision said in Email deliverability to Microsoft email servers:
If we could just override the default Cloudron email configuration on a per app basis, it would be much easier to deal with
You can
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That's very good news, J. Thanks.
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@michaelpope It really isn't for volume sending, just a few dozen normal communications emails per day. Cost doesn't bother me, it's avoiding complexity, and a matter of principle now.
I hear on the X.com vine that even Zoho is having more deliverability issues now, as the screws tighten.
I've never had issues like this in the past. Gone over all the usual checks, and everything is perfectly setup and no blacklists.
Part of me is wondering if faking email headers to look like they are sent from an Exchange server would solve
I'll keep digging, and report back once solved. It's man vs universe now on this one.
Keep the ideas coming, I've an open mind on this one, but have to solve it now, as it wastes so much time not having reliable delivery for just mundane business emails.
@marcusquinn said in Email deliverability to Microsoft email servers:
Keep the ideas coming,
You know, when I realized some emails being served from my MXRoute-hosted domains were going to Spam, I tried including an email from either my @mac.com or @outlook.com stable in the Reply To: field, and then the emails were going through. I included a note to the recipients asking them to reply to the sending email, and that this was an attempt to improve deliverability. I don't have the numbers, stats, or screenshots, but that worked until the regular From address was no longer blocked or labelled as spam (I'm thinking it was about 2 weeks, about 5-6 emails).
A life lived in fear is a life half-lived
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@marcusquinn said in Email deliverability to Microsoft email servers:
Keep the ideas coming,
You know, when I realized some emails being served from my MXRoute-hosted domains were going to Spam, I tried including an email from either my @mac.com or @outlook.com stable in the Reply To: field, and then the emails were going through. I included a note to the recipients asking them to reply to the sending email, and that this was an attempt to improve deliverability. I don't have the numbers, stats, or screenshots, but that worked until the regular From address was no longer blocked or labelled as spam (I'm thinking it was about 2 weeks, about 5-6 emails).
@scooke nice hack!
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@marcusquinn said in Email deliverability to Microsoft email servers:
Keep the ideas coming,
You know, when I realized some emails being served from my MXRoute-hosted domains were going to Spam, I tried including an email from either my @mac.com or @outlook.com stable in the Reply To: field, and then the emails were going through. I included a note to the recipients asking them to reply to the sending email, and that this was an attempt to improve deliverability. I don't have the numbers, stats, or screenshots, but that worked until the regular From address was no longer blocked or labelled as spam (I'm thinking it was about 2 weeks, about 5-6 emails).
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@scooke Interesting! You can make a few alias addresses on iCloud, so could those to separate from your regular email.
@marcusquinn Yes, I've got the full number allowed! I often almost forget what the main email is!
