Sendgrid experiences

Hi.
I am temporarily using Sendgrid now on my Mailman instance. Initial observations have been positive. A list with 100 users is racking up email delivers though, I am on the basic paid account which gives me 50k emails per month. I was hoping to use a cheaper provider and pay overage costs per email on the assumption that I'm seeing a spike in traffic today because people have started getting the messages again.
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.
Hope this helps. Andrew.

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.
-- University of Tsukuba Faculty of Policy and Planning Sciences Tennodai 1-1-1, Tsukuba 305-8573 JAPAN tel/fax: +81-29-853-5091 turnbull@sk.tsukuba.ac.jp https://turnbull.sk.tsukuba.ac.jp/

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
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.

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> 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
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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This message sent to swd@pobox.com

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> Sent: Thursday, May 11, 2023 2:57 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
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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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 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> 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> *Sent:* Thursday, May 11, 2023 2:57 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
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> 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
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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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> Sent: Thursday, May 11, 2023 3:14 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
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.
Mailman-users mailing list -- mailman-users@mailman3.org<mailto:mailman-users@mailman3.org> To unsubscribe send an email to mailman-users-leave@mailman3.org<mailto:mailman-users-leave@mailman3.org> https://lists.mailman3.org/mailman3/lists/mailman-users.mailman3.org/ Archived at: https://lists.mailman3.org/archives/list/mailman-users@mailman3.org/message/...
This message sent to swd@pobox.com<mailto:swd@pobox.com>

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 ~all"
On Thu, May 11, 2023 at 10:16 AM Andrew Hodgson <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> *Sent:* Thursday, May 11, 2023 3:14 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
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 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> 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> *Sent:* Thursday, May 11, 2023 2:57 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
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> 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
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.
Mailman-users mailing list -- mailman-users@mailman3.org To unsubscribe send an email to mailman-users-leave@mailman3.org https://lists.mailman3.org/mailman3/lists/mailman-users.mailman3.org/ Archived at: https://lists.mailman3.org/archives/list/mailman-users@mailman3.org/message/...
This message sent to swd@pobox.com

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-s...>
- 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.
Mailman-users mailing list -- mailman-users@mailman3.org<mailto:mailman-users@mailman3.org> To unsubscribe send an email to mailman-users-leave@mailman3.org<mailto:mailman-users-leave@mailman3.org> https://lists.mailman3.org/mailman3/lists/mailman-users.mailman3.org/ Archived at: https://lists.mailman3.org/archives/list/mailman-users@mailman3.org/message/...
This message sent to swd@pobox.com<mailto:swd@pobox.com>

Reviving this old thread...
Are folks still using Google Workspace or Sendgrid for Mailman?
For Sendgrid, don't all sending addresses have to be verified? How do you get around that? Surely you don't have all list members go through the verification process?
Does Google not have this restriction?
Or am I missing something about how this works? Are people just having all list emails come from the list email address and using the Reply To header or something?

I am running mailman3 in google's cloud. I have a google workspace account with a single authorized user. ($8/month) I use those account credentials and have mailman3 using google's smtp servers as the outbound relay. Works OK. There are still some members of my organization who don't receive list emails, for reasons I've never been able to debug.
On Sun, Sep 28, 2025 at 7:43 AM <tom@tomsmyth.ca> wrote:
Reviving this old thread...
Are folks still using Google Workspace or Sendgrid for Mailman?
For Sendgrid, don't all sending addresses have to be verified? How do you get around that? Surely you don't have all list members go through the verification process?
Does Google not have this restriction?
Or am I missing something about how this works? Are people just having all list emails come from the list email address and using the Reply To header or something?
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This message sent to swd@pobox.com

How do you even debug email/SMTP transactions on google workspace?
On Sun, Sep 28, 2025 at 3:38 PM Stephen Daniel <swd@pobox.com> wrote:
I am running mailman3 in google's cloud. I have a google workspace account with a single authorized user. ($8/month) I use those account credentials and have mailman3 using google's smtp servers as the outbound relay. Works OK. There are still some members of my organization who don't receive list emails, for reasons I've never been able to debug.
On Sun, Sep 28, 2025 at 7:43 AM <tom@tomsmyth.ca> wrote:
Reviving this old thread...
Are folks still using Google Workspace or Sendgrid for Mailman?
For Sendgrid, don't all sending addresses have to be verified? How do you get around that? Surely you don't have all list members go through the verification process?
Does Google not have this restriction?
Or am I missing something about how this works? Are people just having all list emails come from the list email address and using the Reply To header or something?
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https://lists.mailman3.org/archives/list/mailman-users@mailman3.org/message/...
This message sent to swd@pobox.com
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-- Best regards, Odhiambo WASHINGTON, Nairobi,KE +254 7 3200 0004/+254 7 2274 3223 In an Internet failure case, the #1 suspect is a constant: DNS. "Oh, the cruft.", egrep -v '^$|^.*#' ¯\_(ツ)_/¯ :-) [How to ask smart questions: http://www.catb.org/~esr/faqs/smart-questions.html]

Thanks Stephen. I think it would kind of be a dealbreaker if some folks couldn't get mail with no way to remedy.
Are there other hosts? How is this not a bigger issue for Mailman users? Maybe most are big institutions that have their own SMTP relays and dedicated staff to keep deliverability/reputation high?
Or maybe a lot of people are using DMARC mitigation so that the 'from' address is always the list address? I am curious how well that works. I'll start a separate thread on that.
On Sun, Sep 28, 2025 at 8:53 AM Odhiambo Washington <odhiambo@gmail.com> wrote:
How do you even debug email/SMTP transactions on google workspace?
On Sun, Sep 28, 2025 at 3:38 PM Stephen Daniel <swd@pobox.com> wrote:
I am running mailman3 in google's cloud. I have a google workspace account with a single authorized user. ($8/month) I use those account credentials and have mailman3 using google's smtp servers as the outbound relay. Works OK. There are still some members of my organization who don't receive list emails, for reasons I've never been able to debug.
On Sun, Sep 28, 2025 at 7:43 AM <tom@tomsmyth.ca> wrote:
Reviving this old thread...
Are folks still using Google Workspace or Sendgrid for Mailman?
For Sendgrid, don't all sending addresses have to be verified? How do you get around that? Surely you don't have all list members go through the verification process?
Does Google not have this restriction?
Or am I missing something about how this works? Are people just having all list emails come from the list email address and using the Reply To header or something?
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On 2025-09-28 10:23:59 -0400 (-0400), Tom Smyth wrote: [...]
Are there other hosts? How is this not a bigger issue for Mailman users? Maybe most are big institutions that have their own SMTP relays and dedicated staff to keep deliverability/reputation high?
Or maybe a lot of people are using DMARC mitigation so that the 'from' address is always the list address? I am curious how well that works. I'll start a separate thread on that. [...]
Taking the Mailman deployment I help manage for the OpenDev Collaboratory as an example: We use an MTA on our Mailman server to send messages directly to subscriber addresses with no other relay in between. We use a mix of approaches to DMARC-related breakage depending on the particular list:
Some lists are configured to avoid making any changes to messages they relay in order to preserve DKIM signature validity
Some lists conditionally apply DMARC mitigations if a few of the people posting are from domains that make it a problem
Some lists unconditionally apply DMARC mitigations if there's a diversity of domains for posting addresses and more simple approaches fail to maintain deliverability
Some lists don't disable subscribers for frequent bounces in order to prevent a thread involving someone with problematic DKIM signatures from wrecking things
We have not set up any DKIM signing or ARC sealing on the server, and use only the most minimal SPF records ("v=spf1 a ?all").
Maintaining reputation of the server is some work, but not insurmountable. The biggest challenge is from Mailman itself actually, because moderator notifications and messages to the list owner addresses include message bodies which are often spam, and if the moderators use a massmail provider and can't or don't configure it to prevent classifying these then they can end up causing the provider to flag our server as a spam source or auto-reporting it to blocklists. Because of this we frequently end up disabling notifications or blackholing the addresses themselves.
I'll note that we manage with a small number of volunteer admins whose time is spread across hundreds of other servers for various services in the collaboratory, only one of which is running Mailman. As for the scale of our deployment, we host maybe a hundred lists across half a dozen or so domains (one Mailman instance configured for multi-domain operation) supporting a variety of open source projects and nonprofit/volunteer organizations. The largest lists have thousands of subscribers that see at most a few dozen posts in a day, but most of them only have subscriber counts in the tens or hundreds and are far less busy.
Jeremy Stanley

Tom Smyth writes
Are there other hosts?
well I got the domain folks.email (pronounce folksy mail), and run a list there. I could run others.
Maybe most are big institutions that have their own SMTP relays and dedicated staff to keep deliverability/reputation high?
I'm not particularly savvy in the area of deliverability and I should not have to be. As long as I make sure that I follow SPF and DKIM and as long as I don't send and/or forward spam, it should be the receivers who ensure delivery.
-- Written by Thomas Krichel http://openlib.org/home/krichel on his 22032nd day.

Tom Smyth writes:
Are there other hosts?
Many! Costs and services vary enormously, though. I choose to run my own server and MTA because dogfooding, but there are a lot of services that will manage Mailman instances for you, and you just provide the domain and list owners.
How is this not a bigger issue for Mailman users?
Not sure what "this" refers to, SMTP relays? They're a huge issue for instances that don't have other reasons to run an MTA. But if you're hosting email accounts or running MX for an organization you have a lot of other problems, and dealing with the Mailman-specific aspects basically amounts to using the DMARC mitigations, good abusive mail filtering, and implementing the ARC protocol.
Maybe most are big institutions that have their own SMTP relays and dedicated staff to keep deliverability/reputation high?
As far as I can tell, people with just a couple of discussion or non-commercial announce lists, a few dozen members at most, and low traffic, do very well with cheap services that run the MTA and the Mailman instance, and they just handle the list owner stuff. Instances that do more than that typically are serving an organization that provides hosting and SMTP relay service.
Or maybe a lot of people are using DMARC mitigation so that the 'from' address is always the list address?
For most discussion lists, there really is no alternative to "Munge From", at least for p=reject posters. "Stealth DMARC" (where large providers like Gmail require From alignment when they receive messages from themselves) is annoying, but we have an option to deal with that.
Under some circumstances it is possible to run lists that never alter the message, but those are pretty restricted because many jurisdictions require "easy unsubscribe".
-- GNU Mailman consultant (installation, migration, customization) Sirius Open Source https://www.siriusopensource.com/ Software systems consulting in Europe, North America, and Japan

tom@tomsmyth.ca writes:
Are folks still using Google Workspace or Sendgrid for Mailman?
No, but I did until May. I stopped because I wasn't actually using that Mailman instance for anything. As far as I know nothing has changed.
For Sendgrid, don't all sending addresses have to be verified?
Yes.
How do you get around that?
Basic answer, you don't. I used the approach of setting DMARC mitigation to Munge From for all outgoing mail.
I'm not sure that's entirely necessary. I seem to recall that there are documented ways to use Sendgrid to pass through mail with a different From if you set Sender or maybe the envelope From_. But it seemed annoying. Almost all traffic was from me anyway, so it didn't really matter to me. Munge From was easy (by default it even sets Reply-To appropriately for my use case).
I'm currently using a Linode for my mail server. I looked at Google cloud but it didn't seem to have any advantages over Linode, and I was already familiar with Linode. The only problem was Spamhaus had my IPv6 listed, and if you don't pay for the address you effectively get a /128 network from Linode. Spamhaus flat refuses to help in that case. So I configured Postfix to use only IPv4 for outgoing mail and that's working fine for me so far (but small amount of traffic).
-- GNU Mailman consultant (installation, migration, customization) Sirius Open Source https://www.siriusopensource.com/ Software systems consulting in Europe, North America, and Japan

Google has some tools to help debug, which I have experimented with.
I consider having less than 100% reliability to be a reason to find another solution. I started with SendGrid. Google was a substantial improvement. My financial resources are limited, and do not extend to a commercial ISP account. So I have to run this in "the cloud". I choose Google's cloud for various reasons. They both forbid and block any attempt to operate an MTA. I assume other cloud vendors do too. Since I cannot run my own MTA I feel a bit stuck.
Currently I am running a small web site and a modest mailman3 implementation in Google's cloud for less than $25/month, including the cost of the Google Workspace account that lets me use their SMTP relay. Any suggestions on more reliable ways of implementing mailman3 that do not dramatically expand the budget are most welcome.
Thanks!
On Sun, Sep 28, 2025 at 11:32 AM Stephen J. Turnbull <steve@turnbull.jp> wrote:
tom@tomsmyth.ca writes:
Are folks still using Google Workspace or Sendgrid for Mailman?
No, but I did until May. I stopped because I wasn't actually using that Mailman instance for anything. As far as I know nothing has changed.
For Sendgrid, don't all sending addresses have to be verified?
Yes.
How do you get around that?
Basic answer, you don't. I used the approach of setting DMARC mitigation to Munge From for all outgoing mail.
I'm not sure that's entirely necessary. I seem to recall that there are documented ways to use Sendgrid to pass through mail with a different From if you set Sender or maybe the envelope From_. But it seemed annoying. Almost all traffic was from me anyway, so it didn't really matter to me. Munge From was easy (by default it even sets Reply-To appropriately for my use case).
I'm currently using a Linode for my mail server. I looked at Google cloud but it didn't seem to have any advantages over Linode, and I was already familiar with Linode. The only problem was Spamhaus had my IPv6 listed, and if you don't pay for the address you effectively get a /128 network from Linode. Spamhaus flat refuses to help in that case. So I configured Postfix to use only IPv4 for outgoing mail and that's working fine for me so far (but small amount of traffic).
-- GNU Mailman consultant (installation, migration, customization) Sirius Open Source https://www.siriusopensource.com/ Software systems consulting in Europe, North America, and Japan
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Stephen Daniel writes
Any suggestions on more reliable ways of implementing mailman3 that do not dramatically expand the budget are most welcome.
I operate mailman3 + exim4 + spamassassin on a Hetzner dedicated machine and it seems to work fine.
-- Written by Thomas Krichel http://openlib.org/home/krichel on his 22032nd day.

"Stephen" == Stephen Daniel <swd@pobox.com> writes:
Stephen> So I have to run this in "the Stephen> cloud". I choose Google's cloud for various reasons. They Stephen> both forbid and block any attempt to operate an MTA. I Stephen> assume other cloud vendors do too. Since I cannot run my own Stephen> MTA I feel a bit stuck.
I run mailman3 in a VPS that costs around $110 per year. I chose one near to me (in Sydney, Australia); for ease of admin, you need to choose something with low latency to where you're administering it.
The main issue with running your own MTA is it's likely to have relatively low volume, and Google and Microsoft will show it as having a poor reputation until they've seen a certain amount of traffic from it --- and drop or bounce email.
Peter C

I will look into VPS services here in the south-eastern US. Next time I rework on this I'm hoping to go with a containerized implementation, but I think the logic still holds.
Any workaround for the low volume email server? Our volume is less than two messages per week to about 150 subscribers.
On Sun, Sep 28, 2025 at 7:43 PM Peter Chubb <peter@chubb.wattle.id.au> wrote:
"Stephen" == Stephen Daniel <swd@pobox.com> writes:
Stephen> So I have to run this in "the Stephen> cloud". I choose Google's cloud for various reasons. They Stephen> both forbid and block any attempt to operate an MTA. I Stephen> assume other cloud vendors do too. Since I cannot run my own Stephen> MTA I feel a bit stuck.
I run mailman3 in a VPS that costs around $110 per year. I chose one near to me (in Sydney, Australia); for ease of admin, you need to choose something with low latency to where you're administering it.
The main issue with running your own MTA is it's likely to have relatively low volume, and Google and Microsoft will show it as having a poor reputation until they've seen a certain amount of traffic from it --- and drop or bounce email.
Peter C

Peter Chubb via Mailman-users writes
The main issue with running your own MTA is it's likely to have relatively low volume, and Google and Microsoft will show it as having a poor reputation until they've seen a certain amount of traffic from it --- and drop or bounce email.
From what I know, that is correct. Clearly, email being taken over by an oligarchy of tech giants. It should not be that way, and it does not have to be that way. Running your own MTA is an act of resistance.
-- Written by Thomas Krichel http://openlib.org/home/krichel on his 22032nd day.

Stephen Daniel writes:
Currently I am running a small web site and a modest mailman3 implementation in Google's cloud for less than $25/month, including the cost of the Google Workspace account that lets me use their SMTP relay. Any suggestions on more reliable ways of implementing mailman3 that do not dramatically expand the budget are most welcome.
More reliable I can't speak to yet, it's only been about 2 months, but I'm running Mailman, webserver, Cyrus imapd, and the MTA system (including spamfiltering, DKIM and ARC signing, etc) on a Linode, with just the addresses that Linode provides. So far, very easy. I got banned by IP from the get-go by O365, which automatically unbanned me in a very simple procedure (seriously, I expected MSFT to be a *much* bigger PITA). Then I had to disable outgoing SMTP over IPv6 because Spamhaus. (Long story short: they refuse to talk to you about your IPv6 addresses unless you own at least a /64 network.)
Less than $15/month but very low traffic, both mail and web.
-- GNU Mailman consultant (installation, migration, customization) Sirius Open Source https://www.siriusopensource.com/ Software systems consulting in Europe, North America, and Japan

I seem to recall that there are documented ways to use Sendgrid to pass through mail with a different From if you set Sender or maybe the envelope From_.
I'd be really curious about this. I have searched but couldn't find anything. Any chance you have a link to this?
On Sun, Sep 28, 2025 at 11:31 AM Stephen J. Turnbull <steve@turnbull.jp> wrote:
tom@tomsmyth.ca writes:
Are folks still using Google Workspace or Sendgrid for Mailman?
No, but I did until May. I stopped because I wasn't actually using that Mailman instance for anything. As far as I know nothing has changed.
For Sendgrid, don't all sending addresses have to be verified?
Yes.
How do you get around that?
Basic answer, you don't. I used the approach of setting DMARC mitigation to Munge From for all outgoing mail.
I'm not sure that's entirely necessary. I seem to recall that there are documented ways to use Sendgrid to pass through mail with a different From if you set Sender or maybe the envelope From_. But it seemed annoying. Almost all traffic was from me anyway, so it didn't really matter to me. Munge From was easy (by default it even sets Reply-To appropriately for my use case).
I'm currently using a Linode for my mail server. I looked at Google cloud but it didn't seem to have any advantages over Linode, and I was already familiar with Linode. The only problem was Spamhaus had my IPv6 listed, and if you don't pay for the address you effectively get a /128 network from Linode. Spamhaus flat refuses to help in that case. So I configured Postfix to use only IPv4 for outgoing mail and that's working fine for me so far (but small amount of traffic).
-- GNU Mailman consultant (installation, migration, customization) Sirius Open Source https://www.siriusopensource.com/ Software systems consulting in Europe, North America, and Japan
-- Tom Smyth (he/him)

Tom Smyth writes:
I seem to recall that there are documented ways to use Sendgrid to pass through mail with a different From if you set Sender or maybe the envelope From_.
I'd be really curious about this. I have searched but couldn't find anything. Any chance you have a link to this?
No, I don't. I know you can register a whole domain, but that probably isn't what you want. That may be what I vaguely recalled.
Steve
-- GNU Mailman consultant (installation, migration, customization) Sirius Open Source https://www.siriusopensource.com/ Software systems consulting in Europe, North America, and Japan
participants (10)
-
Andrew Hodgson
-
Jeremy Stanley
-
Odhiambo Washington
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Peter Chubb
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Stephen Daniel
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Stephen J Turnbull
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Stephen J. Turnbull
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Thomas Krichel
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Tom Smyth
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tom@tomsmyth.ca