Hi.
Just letting you know that over the weekend I moved from Sendgrid to our Office365 instance similar to what Stephen Daniel did with his Google instance.
Some notes:
- Instead of using authenticated relay I had to create a connecter which allowed relaying from the static IP of the instance. Option 3 in this article is what I did: How to set up a multifunction device or application to send email using Microsoft 365 or Office 365 | Microsoft Learn<https://learn.microsoft.com/en-us/exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-microsoft-365-or-office-365>
- Our list domain is a subdomain of the main domain in Office365. To get this working I had to add lists.domain.com to Office365 and verify the domain DNS records as well as set up DKIM/SPF. I then had to set the domain up as a relay domain and create an outbound connecter for email going to that domain to relay through the Mailman server in order for internal users on our Office365 instance to be able to email the lists.
- This means I can now route list traffic through Office365 as an antispam measure but won’t be doing this as it doesn’t give me recipient validation.
- All mailman specific headers are preserved and bounce processing now works fine.
- Not sure how many emails I can relay through this way but delivery is working fine so far.
Thanks. Andrew.
From: Stephen Daniel <swd@pobox.com> Sent: Thursday, May 11, 2023 3:20 PM To: Andrew Hodgson <andrew@hodgson.io> Cc: Stephen J Turnbull <turnbull@sk.tsukuba.ac.jp>; mailman-users@mailman3.org Subject: Re: [MM3-users] Re: Sendgrid experiences
Also, once I got things running I added some stuff to my DNS records that appears to help with delivery: MYDOMAIN.org TXT 10 minutes "v=spf1 include:_spf.google.com<http://spf.google.com> ~all"
On Thu, May 11, 2023 at 10:16 AM Andrew Hodgson <andrew@hodgson.io<mailto:andrew@hodgson.io>> wrote: Thanks for this. Another option I am thinking of is buying a cheap Linode or other host which isn’t on as many blocklists as Hetzner for outbound mail relay purposes. Hetzner provide a good cheap VPS but their Ips are on a lot of blacklists.
Andrew.
From: Stephen Daniel <swd@pobox.com<mailto:swd@pobox.com>> Sent: Thursday, May 11, 2023 3:14 PM To: Andrew Hodgson <andrew@hodgson.io<mailto:andrew@hodgson.io>> Cc: Stephen J Turnbull <turnbull@sk.tsukuba.ac.jp<mailto:turnbull@sk.tsukuba.ac.jp>>; mailman-users@mailman3.org<mailto:mailman-users@mailman3.org> Subject: Re: [MM3-users] Re: Sendgrid experiences
I'll check my notes. I don't think I did anything with mailman. I am running postfix as my local MTA, and mailman talks to it as normal. In /etc/postfix/main.cf<http://main.cf> I have relayhost = smtp-relay.gmail.com:submission set. It took a bit of playing around to get it running, but its been rock solid since then.
Domains have not been a problem. My google workspace account is MYDOMAIN.dev and all my email lists are MYDOMAIN.org, and everything appears to work just fine.
I took a bunch of cryptic notes on how I got this working. As you would expect, the hard part is getting the authentication and permissions set up. I will send you a private message with a link to my notes.
On Thu, May 11, 2023 at 10:00 AM Andrew Hodgson <andrew@hodgson.io<mailto:andrew@hodgson.io>> wrote: Hi.
Thanks for the recommendation on the Google Workspace. How did you set this up in terms of the domain, since I don’t want to use Google Workspace as the main email provider for this domain. Also did you have to set anything special in Mailman?
Thanks. Andrew.
From: Stephen Daniel <swd@pobox.com<mailto:swd@pobox.com>> Sent: Thursday, May 11, 2023 2:57 PM To: Andrew Hodgson <andrew@hodgson.io<mailto:andrew@hodgson.io>> Cc: Stephen J Turnbull <turnbull@sk.tsukuba.ac.jp<mailto:turnbull@sk.tsukuba.ac.jp>>; mailman-users@mailman3.org<mailto:mailman-users@mailman3.org> Subject: Re: [MM3-users] Re: Sendgrid experiences
I would definitely look for alternatives to SendGrid. I tried using them and had a very poor rate of people actually getting my emails, even when I temporarily upgraded to an expensive plan with a dedicated IP address. I'm currently hosting mailman in Google Cloud and relaying outbound mail through a Google Workspace account. It's working OK. The workspace account costs me $6/month for basically unlimited mail relay.
On Thu, May 11, 2023 at 9:50 AM Andrew Hodgson <andrew@hodgson.io<mailto:andrew@hodgson.io>> wrote: Stephen J Turnbull wrote:
2023-05-10 03:49 に Andrew Hodgson wrote:
Sendgrid is maintaining the Message-Id header which is good for archiving. It is re-writing the Return-Path header though which means that bounce handling in Mailman won't work, but I think all the services do this in some way so I am happy to live with that for the moment.
How does it rewrite the Return-Path? Returned mail is not something that such a service would be able to handle properly (although they can help with apparently returned spam). If mail is legitmately sent and returned as undeliverable, only the author or their agent will know how to handle it. So such >services should provide some way to find out about returned mail.
An example: Return-Path: bounces+[Sendgrid GUID]-andrew=hodgson.io@em6096.lists.hodgsonfamily.org<mailto:hodgson.io@em6096.lists.hodgsonfamily.org>
Sendgrid provide information about bounces but crucially that bounce isn't forwarded back to the original return-path sender (i.e, Mailman).
A few people have pointed out they can provide list hosting at a cheaper cost than Sendgrid so I'm looking for alternatives again.
Andrew.
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