issue with email delivery going through Cloudron mailing lists.

[avatar1024]

@girish Hi Girish, thanks for looking into this. That could be it, although it looks like when I do the redirect filter with roundcube to replicate the email list behaviour there is also a SRS rewrite and emails are going through fine.
I could send you the event logs if you want to compare the two?

[girish]

@avatar1024 good point about redirection not being affected! I will add this into the next release checklist.

[d19dotca]

Just wanted to check in on this. It seems I am running into this issue from one particular domain. Same Gmail reply status. Deferred mail according to Gmail, and it’s taking hours to days to ever be accepted by Gmail. Oddly it only affects one domain but I think it’s because it’s also the only domain that forwards via distribution lists in Cloudron to a few Gmail addresses.

Can we please consider this? I see mention of “add this into the next release checklist”, but not sure if that ever got into it or not, or if that was unrelated. Do we have a fix for this Gmail delivery issue when using the Cloudron mailing lists feature?

Upstream error: 421 4.7.28 Gmail has detected an unusual rate of unsolicited mail. To protect 4.7.28 our users from spam, mail has been temporarily rate limited. For 4.7.28 more information, go to 4.7.28  https://support.google.com/mail/?p=UnsolicitedRateLimitError to 4.7.28 review our Bulk Email Senders Guidelines. 6a1803df08f44-6fb09b2f3b8si64915186d6.375 - gsmtp

The mailing list is rarely used and only sends to maybe 18 emails addresses, only 5 or 6 of which are Gmail accounts. It’s for a residential strata mailing lists so it’s a small amount of emails involved and a small group of people, they maybe send a few a day and then weeks can go by with nothing. So it definitely isn’t an unsolicited mass emailing, the response from Google seems a little bit misleading there.

My guess from reading the above is Gmail is detecting the Cloudron mailing lists as bulk email, and deferring it as a result. Seems the workaround is to use a mailbox with mail forwarding instead, which I haven’t tried yet but may try tomorrow given the messages above in this post.

Any insights into how we can really fix this though so that we can use Cloudron mailing lists to Gmail?

[d19dotca]

Attached is an image, as you can see this is severely impacting the ability for the strata owners to communicate to anyone on the list which goes to a Gmail account. (I originally tried to uploaded a larger screenshot showing more lines but the forum software prevented it, saying it was too large.)

[robi]

Are there any mail gateway routers? So you can use different services with known good deliverability?

[james]

@avatar1024 was this resolved?

[avatar1024]

I can't tell as I stopped using Cloudron mailing list a while ago because of this. But clearly others (e.g. @d19dotca) seem to still have the problem so looks like it hasn't been solved.

[jdaviescoates]

@avatar1024 said in issue with email delivery going through Cloudron mailing lists.:

I stopped using Cloudron mailing list a while ago because of this

Out of interest, what you using instead?

[d19dotca]

@james said in issue with email delivery going through Cloudron mailing lists.:

@avatar1024 was this resolved?

No, this hasn’t been resolved. This still needs to be improved in Cloudron mailing lists, please.

[d19dotca]

@jdaviescoates said in issue with email delivery going through Cloudron mailing lists.:

@avatar1024 said in issue with email delivery going through Cloudron mailing lists.:

I stopped using Cloudron mailing list a while ago because of this

Out of interest, what you using instead?

I think they were using the workaround of creating a mailbox and logging into roundcube to setup mail forwarding, so it kind of acts like the Cloudron mailing list in a way, but seems to be more reliable and doesn’t trigger Gmail’s “mass mail” protections.

[avatar1024]

@d19dotca said in issue with email delivery going through Cloudron mailing lists.:

I think they were using the workaround of creating a mailbox and logging into roundcube to setup mail forwarding, so it kind of acts like the Cloudron mailing list in a way, but seems to be more reliable and doesn’t trigger Gmail’s “mass mail” protections.

That's correct and also started using Lismonk for larger distribution lists.

[jdaviescoates]

Just to add, I've hit this too.

I've got a small Cloudron mailing list that includes a bunch of Gmail address. In the past I think it's been sending to them fine, but the most recent send to the list (which was sent from a Google Workspace email account that is also on the list) generated this error:

Upstream error: 421 4.7.28 Gmail has detected this message exceeded its quota for sending 4.7.28 messages with the same Message-ID. To best protect our users, the 4.7.28 message has been temporarily rejected. For more information, go to 4.7.28 https://support.google.com/mail/answer/188131 a640c23a62f3a-afcdd03a4b4si214278366b.769 - gsmtp

I guess I'll have to resort to sending these messages out another way too

[jdaviescoates]

@avatar1024 said in issue with email delivery going through Cloudron mailing lists.:

also started using Lismonk for larger distribution lists.

Is that what you're still doing? Do those somehow magically get through to Gmail addresses OK?

[avatar1024]

@jdaviescoates Well, this is what I do for distribution list and it seems to work fine with Gmail addresses. But I have to say it isn't really a replacement for Cloudron lists. I find the current email situation really quite tricky on Cloudron, given:

1. issues with delivery on forwards to some providers like Gmail
2. issues with delivery when using an external SMTP (likely related to point 1) when trying to overcome bad IP rep (which with MS domains is a recurring issue with MS stupid IP range bans).

For work I have to now consider moving all our mailboxes out of Cloudron...which I would really want to avoid because of:

1. faff
2. because I love Cloudron and wanna promote it (but my users are getting pissed because of email problems).

@staff if you don;t really want to focus of changing the mailing function on Cloudron for now (and I totally respect and understand that this may not be your priority), can you advise on a working solution to use a address@domain.coop (with domain.coop being the Cloudron domain) which can be use as a list, where:

1. some mailboxes on this domain being hosted on Cloudron (so the MX has to remain pointing to the Cloudron server)
2. and while using an external SMTP server to ensure reliable email delivery