issue with email delivery going through Cloudron mailing lists.

[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

[d19dotca]

I was using ChatGPT for some assistance on this, as I'm still struggling with this issue off-and-on-again, and it recommended applying this to the Haraka configuration:

[outbound.limits]
gmail.com=1/30s

Essentially rate limiting delivery to Gmail which should lessen the likelihood of being rate limited by Gmail. Is there a way for us to configure this at all for testing purposes? I can't seem to create the outbound.limits file due to the read-only file system in the mail container, so I'm not sure how I can try this.

Interestingly though, I noticed today that this issue only seems to happen if sending from a hotmail.com / outlook.com address to the hosted Cloudron domain name which then forwards to the gmail.com address will this issue be triggered. If I send to the same distribution list from my other email addresses, it seems to not trigger the rate limiting response. So it seems possibly related to the sending domain originally before the hosted domain itself, which Gmail occasionally seems to have problems with.

Since the error is also sometimes Gmail has detected this message exceeded its quota for sending 4.7.28 messages with the same Message-ID, is there any possibility that Cloudron's mailing list feature could rotate the message-ID to avoid Gmail flagging it?

[avatar1024]

Do we know why this has been marked as solved?

[girish]

I read the thread quickly but it relates to Gmail sending quotas. Not sure what Cloudron can do here?

[d19dotca]

@girish Having the option to add rate limiting outbound to certain domains in Haraka would be nice to have.

[girish]

I think that message from gmail is the generic one saying it doesn't want your email from the IP. Are you actually sending 100s of emails to gmail ? Or is gmail rate limit so low? Happy to read up on some gmail docs, but I can't really find any note on specific limits.

[d19dotca]

@girish No I wasn’t and still don’t, that’s why I mentioned in an earlier comment that it was a little bit misleading. I’m just saying now though since this was marked as solved because you weren’t sure what more could be done, I’m just adding that exposing the ability to set rate limits in Haraka could be nice as a workaround and giving more control to users.

[girish]

@d19dotca ah ok!

[avatar1024]

@girish said:

I read the thread quickly but it relates to Gmail sending quotas. Not sure what Cloudron can do here?

@girish Surely there is something to be done in the implementation of mailing lists since it only fails when using the native claudron mailing list function but works fine when "reproducing" the mailing function using forwarding in roundcube (I.e. sending to one mailbax that forwards to the same addresses than those in the mailing list).

With Cloudron 10 it may be redundant given you've done an overhaul of the mailing function, but I wonder whether the new implementation solves this problem?

[girish]

With Cloudron 10, the forwarding logic is based on sieve. So, it's identical to roundcube.