4 ms·

Subnet level blocking is certainly a thing, but I’m setting up new domains routinely and Outlook works fine. Even with cheap / free domains. Lack of verbose fe

by aj3 5y ago

Subnet level blocking is certainly a thing, but I’m setting up new domains routinely and Outlook works fine. Even with cheap / free domains. Lack of verbose feedback / delivery errors makes debugging issues in your own really hard, so you might want to contact someone who knows a thing or two about emails for help.

vgb2k18 5y ago
> I’m setting up new domains routinely and Outlook works fine. Even with cheap / free domains. You say domains To ensure we're speaking to, not past, each other it will be essential to clarify one thing: what do you mean precisely by "setting up new domains", "cheap/ free domains"? Domains, I'm not interested in chatting about those, but IP address space, then yes I'm all ears. If you can reliably setup new, fully self-hosted mail servers (i.e., not using SendGrid, MailGun etc), with port 25 open for both send and receive, on cheap, accessible VPS servers... And... Send email messages from those new servers directly to your Outlook's inbox. Then you Good Sir, have the secret sauce. *Caveat: AWS does have a lot of un-blacklisted IP address space, however, port 25 remains blocked for new customers without a "valid use-case" and an unspecified amount of payment history. Similar for Azure. So if your methodology is built around AWS/Azure then kudos, but for new-comers, it would be unrealistic from my experience to suggest the path forward will be without major hurdles and/or delays. The lack of verbose feedback in the rejection reason from Outlook was, as I see it, a feature not a bug. A bit of friction to turn away the undetermined ones. I followed the trail of clues from the top search results of the error message and eventually got my new IP unblocked through the proper channel. So... I have made it from bottom tier (outright rejection of emails), to 2nd-bottom tier (directly to spam/junk folder). Next: build domain/ip reputation ever so slowly.
- aj3 5y ago
  Yeah, I didn't want to get stuck in details, but I'm setting up a couple of new mailservers (freshly registered domains, self-hosted VPS at cheap cloud providers (DO, Hetzner, OVH, AWS). And they do get delivered directly into Outlook, Google, Protonmail and other major providers after two days tops (some still employ greylisting for fresh IPs/domains). There's no secret sauce but there is a myriad of ways to shoot yourself in the foot when setting up a mail server from scratch. E.g. many standard setups may try delivering email over IPv6 if available which currently is a terrible idea but might be completely opaque to the user. Obviously, the results will also depend on what is it that you're sending as everyone uses point-based (or even ML) systems nowadays and headers + contents can earn you either negative or positive points.
  - vgb2k18 5y ago
    Oh boy, thanks for the detail, love it. You've probably been more fortunate than you can appreciate for now. I mean, I've not yet had a DO IP which wasn't listed blocked by SNDS (Outlook private block-lists): https://sendersupport.olc.protection.outlook.com/snds/ipStatus.aspx https://sendersupport.olc.protection.outlook.com/snds/ipStat... Would be interested to hear from others who've acquired new DO IPs that weren't blocked on that list though. Change my view of the whole scenario.

by aj3 5y ago

vgb2k18 5y ago

> I’m setting up new domains routinely and Outlook works fine. Even with cheap / free domains. You say domains To ensure we're speaking to, not past, each other it will be essential to clarify one thing: what do you mean precisely by "setting up new domains", "cheap/ free domains"? Domains, I'm not interested in chatting about those, but IP address space, then yes I'm all ears. If you can reliably setup new, fully self-hosted mail servers (i.e., not using SendGrid, MailGun etc), with port 25 open for both send and receive, on cheap, accessible VPS servers... And... Send email messages from those new servers directly to your Outlook's inbox. Then you Good Sir, have the secret sauce. *Caveat: AWS does have a lot of un-blacklisted IP address space, however, port 25 remains blocked for new customers without a "valid use-case" and an unspecified amount of payment history. Similar for Azure. So if your methodology is built around AWS/Azure then kudos, but for new-comers, it would be unrealistic from my experience to suggest the path forward will be without major hurdles and/or delays. The lack of verbose feedback in the rejection reason from Outlook was, as I see it, a feature not a bug. A bit of friction to turn away the undetermined ones. I followed the trail of clues from the top search results of the error message and eventually got my new IP unblocked through the proper channel. So... I have made it from bottom tier (outright rejection of emails), to 2nd-bottom tier (directly to spam/junk folder). Next: build domain/ip reputation ever so slowly.

aj3 5y ago
Yeah, I didn't want to get stuck in details, but I'm setting up a couple of new mailservers (freshly registered domains, self-hosted VPS at cheap cloud providers (DO, Hetzner, OVH, AWS). And they do get delivered directly into Outlook, Google, Protonmail and other major providers after two days tops (some still employ greylisting for fresh IPs/domains). There's no secret sauce but there is a myriad of ways to shoot yourself in the foot when setting up a mail server from scratch. E.g. many standard setups may try delivering email over IPv6 if available which currently is a terrible idea but might be completely opaque to the user. Obviously, the results will also depend on what is it that you're sending as everyone uses point-based (or even ML) systems nowadays and headers + contents can earn you either negative or positive points.
- vgb2k18 5y ago
  Oh boy, thanks for the detail, love it. You've probably been more fortunate than you can appreciate for now. I mean, I've not yet had a DO IP which wasn't listed blocked by SNDS (Outlook private block-lists): https://sendersupport.olc.protection.outlook.com/snds/ipStatus.aspx https://sendersupport.olc.protection.outlook.com/snds/ipStat... Would be interested to hear from others who've acquired new DO IPs that weren't blocked on that list though. Change my view of the whole scenario.