issue with email delivery going through Cloudron mailing lists.

[jdaviescoates]

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

For 4.7.28 more information, go to 4.7.28 https://support.google.com/mail/?p=UnsolicitedRateLimitError

Based on what it says there and what you've said here my guess is that it thinks you're too rapildy emailing the 5 or 7 gmail addresses in the groups where this is an issue. It seems like google thinks you're very rapidly separately emailing those 5 or 7 people rather than realising it's one email sent to a list.

But I've no idea what you could do about it, if anything

[avatar1024]

@jdaviescoates Thanks! I wonder if anyone can reproduce this to see if it is a general issue with Gmail, or something specific to my server.

Also it seems weird that would happen with only 5 or 7 people. I can easily imagine (and I'm sure I did) sending a personal email to 5+ recipients that have gmail addresses without it causing an issue.

@staff what do you reckon about the above problem? Is there anything that could be done to mitigate this?

Thank you!

[avatar1024]

Ok so I've done additional testing:

1. I created a brand new list like earlier with a few people but only one gmail address: everything works fine.
2. I added 5 more gmail addresses: errors started to show up
3. I created a mailbox and in roundcude within which I created a filter that forwards all emails to exactly the same 6 gmail addresses + the non gmail addresses as in 2.: everything works fine!!

So the issue really ONLY happens when using the mailing list function.

Sadly 3. is not really a workaround as those lists with issues are closed lists and so I would need to set a rule to the filter so it only allows emails from those people (this would work to reproduce the closed list feature of Cloudron but it would be a tedious workaround and not easily self managed by the people on this Cloudron as they aren't very tech savy...they're ok with Cloudron list feature but probably not with going into mailboxes, set/change filters etc.).

[girish]

I think this is related to SRS rewriting for mailing lists. IIRC, gmail does not like SRS Other vendors like outlook/hotmail want SRS. I guess the mail sever can maintain some sort of a list of who supports SRS and who doesn't.

[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.